SecProbe.io

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 May 6, 2025

 Via Edgar

 U.S. Securities and Exchange Commission

 Division of Corporation Finance

 Office of Finance

 Washington, D.C. 20549

 Attention: Aisha Adegbuyi

 Re:
 Request for Acceleration

 Old Second Bancorp, Inc.
 (the "Registrant")

 Registration Statement
 on Form S-4 (File No. 333-286687)

 Dear Sir or Madam:

 Pursuant to Rule 461
under the Securities Act of 1933, as amended (the " Securities Act "), the Registrant hereby requests that the
effective date for the above-referenced Registration Statement be accelerated so that it will be declared effective under the Securities
Act at 9:30 a.m., Eastern Time, on Thursday, May 8, 2025, or as soon thereafter as practicable.

 Please contact our counsel,
Brittany McIntosh, at (864) 376-2326 with any questions you may have concerning this letter, or if you require any additional information.
Please notify Ms. McIntosh when this request for acceleration of effectiveness of the Registration Statement has been granted.

 Very truly yours,

 Old Second Bancorp, Inc.

 By:
 /s/ Bradley S. Adams

 Bradley S. Adams

 EVP, Chief Operating Officer and Chief
 Financial Officer

 37 South River Street, Aurora, Illinois 60507

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 May 1, 2025

James L. Eccher
Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, Illinois 60507

 Re: Old Second Bancorp, Inc.
 Registration Statement on Form S-4
 Filed April 23, 2025
 File No. 333-286687
Dear James L. Eccher:

 This is to advise you that we have not reviewed and will not review your
registration
statement.

 Please refer to Rules 460 and 461 regarding requests for acceleration.
We remind you
that the company and its management are responsible for the accuracy and
adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action
by the staff.

 Please contact Aisha Adegbuyi at 202-551-8754 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of Finance
cc: Brittany M. McIntosh, Esq.
</TEXT>
</DOCUMENT>

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​

Old Second Bancorp, Inc.

37 South River Street

Aurora, Illinois 60507

(630) 892-0202

​

​

August 24, 2023

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

100 F Street, NE

Washington, D.C.  20549

Attention:      Aisha Adegbuyi

Re:

 Old Second Bancorp, Inc. (the “Company”)

 Request for Acceleration of Effectiveness of Form S-3

 SEC File No. 333-274068 (the “Registration Statement”)

​

Dear Ms. Adegbuyi:

The Company hereby requests acceleration of the effective date of the above-referenced Registration Statement to 4:00 p.m., Eastern Time, on Monday, August 28, 2023, or as soon thereafter as practicable.

The staff should feel free to contact Brennan Ryan of Nelson Mullins Riley & Scarborough LLP, the Company’s legal counsel, at (404) 322-6444 with any questions or comments.

 Very truly yours,

 Old Second Bancorp, Inc.

 /s/ Bradley S. Adams

 Bradley S. Adams

 Executive Vice President, Chief Operating Officer, and Chief Financial Officer

​

​

United States securities and exchange commission logo
August 23, 2023
James Eccher
Chairman of the Board, President, Chief Executive Officer and Director
Old Second Bancorp, Inc.
37 South River Street Aurora,
Illinois 60507
Re:Old Second Bancorp, Inc.
Registration Statement on Form S-3
Filed August 18, 2023
File No. 333-274068
Dear James Eccher:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Aisha Adegbuyi at 202-551-8754 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:       Brennan Ryan

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October 19, 2021

Via Edgar

U.S. Securities and Exchange Commission

Division of Corporation Finance

Office of Finance

Washington, D.C. 20549

Attention: Tonya K. Aldave

    Re:
    Request for Acceleration

    Old Second Bancorp, Inc. (the “Registrant”)

    Registration Statement on Form S-4 (File No. 333-259964)

Dear Sir or Madam:

Pursuant to Rule 461
under the Securities Act of 1933, as amended (the “Securities Act”), the Registrant hereby requests that the
effective date for the above-referenced Registration Statement be accelerated so that it will be declared effective under the Securities
Act at 4:00 p.m., Eastern Time, on Thursday, October 21, 2021, or as soon thereafter as practicable.

Please contact our counsel,
Brennan Ryan, at (404) 322-6218 with any questions you may have concerning this letter, or if you require any additional information.
Please notify Mr. Ryan when this request for acceleration of effectiveness of the Registration Statement has been granted.

    Very truly yours,

    Old Second Bancorp, Inc.

    By:
    /s/ Bradley S. Adams

    Bradley S. Adams

    Chief Financial Officer

37 South River Street, Aurora, Illinois 60507

United States securities and exchange commission logo
October 6, 2021
James L. Eccher
Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60507
Re:Old Second Bancorp, Inc.
Registration Statement on Form S-4
Filed October 1, 2021
File No. 333-259964
Dear Mr. Eccher:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Tonya K. Aldave at (202) 551-3601 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:       Brennan Ryan, Esq.

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Old Second Bancorp, Inc.

37 South River Street

Aurora, Illinois 60507

(630) 892-0202

​

​

August 18, 2020

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

100 F Street, NE

Washington, D.C.  20549

Attention:      Donald Field

Re:

 Old Second Bancorp, Inc. (the “Company”)

 Request for Acceleration of Effectiveness of Form S-3

 SEC File No. 333-243746 (the “Registration Statement”)

Dear Mr. Field:

The Company hereby requests acceleration of the effective date of the above-referenced Registration Statement to 4:00 p.m., Eastern Time, on Thursday, August 20, 2020, or as soon thereafter as practicable.

The staff should feel free to contact Brennan Ryan of Nelson Mullins Riley & Scarborough LLP, the Company’s legal counsel, at (404) 322-6444 with any questions or comments.

 Very truly yours,

 Old Second Bancorp, Inc.

 /s/ Bradley S. Adams

 Bradley S. Adams

 Executive Vice President and Chief Financial Officer

​

United States securities and exchange commission logo
August 14, 2020
James L. Eccher
Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, Illinois 60507
Re:Old Second Bancorp, Inc.
Registration Statement on Form S-3
Filed August 10, 2020
File No. 333-243746
Dear Mr. Eccher:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Donald Field at 202-551-3680 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance

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Old Second Bancorp, Inc.

37 South River Street

Aurora, Illinois 60507

(630) 892-0202

August 10, 2017

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

100 F Street, NE

Washington, D.C.  20549

Attention:      Christopher Dunham, Staff Attorney

Re:

Old Second Bancorp, Inc. (the “Company”)

Request for Acceleration of Effectiveness of Form S-3

SEC File No. 333-219680 (the “Registration Statement”)

Dear Mr. Dunham:

The Company hereby requests acceleration of the effective date of the above-referenced Registration Statement to 10:00 a.m., Eastern Time, on Friday, August 11, 2017, or as soon thereafter as practicable.

The staff should feel free to contact Brennan Ryan of Nelson Mullins Riley & Scarborough LLP, the Company’s legal counsel, at (404) 322-6218 with any questions or comments.

Very truly yours,

Old Second Bancorp, Inc.

/s/ Bradley S. Adams

Bradley S. Adams

Executive Vice President and   Chief Financial Officer

Mail Stop 4720

August 8, 2017

Bradley S. Adams
Executive Vice President, Chief Financial Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60507

Re: Old Second Bancorp, Inc.
  Registration Statement on Form S-3
Filed  August 3, 2017
  File No.  333-219680

Dear Mr. Adams :

This is to advise you that we have not  reviewed and will not review your registration
statement .

Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.

Please  contact Christopher Dunham, Staff Attorney, at (202) 551 -3783  with any
questions .

Sincerely,

 /s/ Dietrich A. King

Dietrich A. King
Assistant Director
Office of Financial Services

cc: J. Brennan Ryan , Esq.

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December 1, 2016

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

100 F Street, NE

Washington, D.C.  20549

Attention:      Katelyn Donovan

Re:

Old   Second Bancorp, Inc.

Request   for Acceleration of Effectiveness of Form S-3

SEC File No. 333-214459   (“Registration Statement”)

Dear Ms. Donovan:

On behalf of Old Second Bancorp, Inc., as registrant, the undersigned officer hereby requests that the effective date for the Registration Statement, as amended, be accelerated so that it will be declared effective at 1:00 p.m. (Washington, D.C. time) or as soon as practicable thereafter on Friday, December 2, 2016.

The staff should feel free to contact Bill Fay of Barack Ferrazzano Kirschbaum & Nagelberg LLP, the registrant’s legal counsel, at (312) 629-7470 with any questions or comments.

Very truly   yours,

Old Second   Bancorp, Inc.

/s/ J. Douglas   Cheatham

J. Douglas   Cheatham

Executive Vice   President and Chief Executive Officer

Mail Stop 4720
November 14, 2016

James L. Eccher
President and Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60507

Re: Old Second Bancorp, Inc.
  Registration Statement on Form S-3
Filed  November 4, 2016
  File No.  333-214459

Dear Mr. Eccher :

This is to advise you that we have not  reviewed and will not review your registration
statement .

Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.

Please  contact Katelyn Donovan, Law Clerk , at (202) 551 -8636 with any questions.

Sincerely,

 /s/ Era Anagnosti

Era Anagnosti
Legal Branch Chief
Office of Financial Services

cc: Abdul R. Mitha
 Barack Ferrazzano Kirschbaum & Nagelberg LLP

April 3, 2014

Via E -mail
William B. Skoglund
Chairman and Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60506

Re: Old Second Bancorp,  Inc.
Form 10 -K for Fiscal Year Ended  December 31, 2013
Filed February 26, 2014
Form 10 -K for Fiscal Year Ended  December 31, 2012
Filed March 20, 2013
Form 10 -Q for Fiscal Quarter Ended  September 30, 2013
Filed November 12, 2013
File No. 000-10537

Dear Mr. Skoglund :

We have completed our review of your filings.  We remind you that our comments or
changes to disclosure in response to our comments do not foreclose the Commission from taking
any action with respect to the company or the filing s and the company may not assert staff
comments as a defense in any proceeding initiated by the Commission or any person under the
federal securities laws of the United States.  We urge all persons who are responsible for the
accuracy and adequacy of  the disclosure in the filing s to be certain that the filing s include the
information the Securities Exchange Act of 1934 and all applicable rules require.

Sincerely,

 /s/ Michael Clampitt

Michael Clampitt
Senior Counsel

cc: Via E -mail
 J. Douglas Cheatham
 Robert M. Fleetwood , Esq.

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April 1, 2014

VIA EDGAR

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.

Amendment No. 2 to Registration Statement on Form S-1

Filed March 26, 2014

File No. 333-193424

Dear Mr. Clampitt:

We are in receipt of your letter dated April 1, 2014, concerning the above-captioned filings of Old Second Bancorp, Inc. (the “Company”), and hereby submit the following responses to the comments contained therein.  To facilitate your review, we have repeated your comment in your April 1, 2014 letter below in bold italic type, followed by our responses.

Amendment No. 2 to Registration Statement on Form S-1

Exhibit 23.1

Consent to Independent Registered Public Accounting Firm

1.              The staff notes the consent refers to the report dated March 26, 2014 while the report in the Form 10-K is dated February 26, 2014.  Please revise or advise.

In response to this comment, the Company has filed Amendment No. 3 to the Registration Statement on Form S-1 to amend the consent of the Company’s independent registered public accounting firm, filed as Exhibit 23.1 to Amendment No. 2 to the Registration Statement on Form S-1, to correct the date of the report.

*  * * * *

The Company hereby acknowledges that:

·                  The Company is responsible for the adequacy and accuracy of the disclosure in the filings;

·                  Staff comments or changes to disclosure in response to Staff comments do not foreclose the Commission from taking any action with respect to the filing; and

·                  The Company may not assert Staff comments as a defense in any proceeding initiated by the Commission or any person under the federal securities laws of the United States.

The Company believes the foregoing provides a complete response to the Comment Letter.  If you have questions regarding the foregoing or require any additional information, please feel free to contact me directly at (630) 906-5484 or dcheatham@oldsecond.com or William Skoglund, Chairman and President of the Company, at (630) 906-5483 or wskoglund@oldsecond.com.

Sincerely,

/s/   J. Douglas Cheatham

J.   Douglas Cheatham

Executive   Vice President and Chief Financial Officer

2

April 1, 2014

Via E -mail
William B. Skoglund
Chairman and Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60506

Re: Old Second Bancorp,  Inc.
Amendment No. 2  to Registration Statement on Form S -1
Filed March 26 , 2014
  File No. 333 -193424

Dear Mr. Skoglund :

We have reviewed the above referenced filing  and have the following comments.  In
some of our comments, we may ask you to provide us with information so we may better
understand your disclosure.

Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.

After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments .

Amendment No. 2  to Registration Statement on Form S -1

Exhibit 23.1

Consent of Independent Registered Public Accounting Firm

1. The staff notes the consent refers to the report dated March 26, 2014 while the report in
the Form 10 -K is dated February 26 , 2014.  Please revise or advise.

We urge all persons who are responsible for the accuracy and adequacy of the disclosure
in the filing to be certain that the filing includes the information the Securities Act of 1933 and
all applicable Securities Act rul es require.   Since the company and its management are in
possession of all facts relating to a company’s disclosure, they are responsible for the accuracy
and adequacy of the disclosures they have made.

William B. Skoglund
Old Second Bancorp, Inc.
April 1, 2014
Page 2

 Notwithstanding our comments, in the event you request acceleration of the effective date
of the pending registration statement please provide a written statement from the company
acknowledging that:

 should the Commission or the staff, acting pursuant to delegated authority, declare the
filing effecti ve, it does not foreclose the Commission from taking any action with respect
to the filing;

 the action of the Commission or the staff, acting pursuant to delegated authority, in
declaring the filing effective, does not relieve the company from its full r esponsibility for
the adequacy and accuracy of the disclosure in the filing; and

 the company may not assert staff comments and the declaration of effectiveness as a
defense in any proceeding initiated by the Commission or any person under the federal
securities laws of the United States.

Please refer to Rules 460 and 461 regarding requests for acceleration.  We will consider a
written request for acceleration of the effective date of the registration statement as confirmation
of the fact that those requ esting acceleration are aware of their respective responsibilities under
the Securities Act of 1933 and the Securities Exchange Act of 1934 as they relate to the proposed
public offering of the securities specified in the above registration statement.  Ple ase allow
adequate time for us to review any amendment prior to the requested effective date of the
registration statement.

You may contact Chris Harley at (202) 551 -3695 or David Irving at (202) 551 -3321  if
you have questions regarding comments on t he financial statements and related matters.  Please
contact David Lin at (202) 551 -3552  or me at (202) 551 -3434  with any other questions.

Sincerely,

 /s/ Michael Clampitt

Michael Clampitt
Senior Counsel

cc: Via E -mail
 J. Douglas Cheatham
 Robert M. Fleetwood , Esq.

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Old Second Bancorp, Inc.

37 South River Street

Aurora, Illinois 60506

March 31, 2014

VIA EDGAR

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.

Request for Acceleration of Effectiveness of

Registration Statement on Form S-1 (File No. 333-193424)

Ladies and Gentlemen:

Pursuant to Rule 461 under the Securities Act of 1933 (the “Securities Act”), Old Second Bancorp, Inc., a Delaware corporation (the “Company”), respectfully requests that the effective date of the above-referenced Registration Statement on Form S-1 be accelerated by the Securities and Exchange Commission (the “Commission”) so that the Registration Statement, as then amended, will become effective under the Securities Act at 1:00 p.m. (Eastern Standard Time) on Thursday, April 3, 2014, as soon as practicable thereafter or at such later time as the Company or its counsel may orally request via telephone call to the staff of the Commission.

The undersigned officer of the Company, on behalf of the Company, acknowledges that:

·                                    should the Commission or the staff, acting pursuant to delegated authority, declare the filing effective, it does not foreclose the Commission from taking any action with respect to the filing;

·                                    the action of the Commission or the staff, acting pursuant to delegated authority, in declaring the filing effective, does not relieve the Company from its full responsibility for the adequacy and accuracy of the disclosure in the filing; and

·                                    the Company may not assert staff comments and the declaration of effectiveness as a defense in any proceeding initiated by the Commission or any person under the federal securities laws of the United States.

We request that we be notified of such effectiveness by a telephone call to Robert M. Fleetwood at (312) 629-7329 or Gregory V. Demo at (312) 629-5182, both of Barack Ferrazzano Kirschbaum & Nagelberg LLP, and that such effectiveness also be confirmed in writing.

Very truly yours,

/s/ J. Douglas Cheatham

J. Douglas Cheatham

Executive Vice President and Chief Financial Officer

cc:

Mr. Robert M. Fleetwood

Mr. Gregory V. Demo

Barack Ferrazzano Kirschbaum & Nagelberg LLP

200 West Madison Street, Suite 3900

Chicago, Illinois 60606

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Keefe, Bruyette & Woods, Inc.

as representative of the several underwriters

787 Seventh Avenue

4th Floor

New York, New York 10019

March 31, 2014

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.
 Registration Statement on Form S-1
 Registration File No. 333-193424

Ladies and Gentlemen:

In accordance with Rule 461 of the Securities Act of 1933, as amended (the “Act”), we hereby join in the request of Old Second Bancorp, Inc. (the “Company”) for acceleration of the effective date of the above-named Registration Statement, as amended, so that it becomes effective at 1:00 p.m. (Washington, D.C. time) on Thursday, April 3, 2014, or as soon thereafter as practicable.

Pursuant to Rule 460 under the Act, we wish to advise you that we have effected distribution of 800 copies, in the aggregate, of the Company’s Preliminary Prospectus issued March 26, 2014 through the date hereof to prospective underwriters, institutions and others.

We have been informed by the participating underwriters that they will comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

Very   truly yours,

KEEFE,   BRUYETTE & WOODS, INC.

By:

/s/   Allen G. Laufenberg

Name:

Allen   G. Laufenberg

Title:

Managing   Director

2

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Old Second Bancorp, Inc.

37 South River Street

Aurora, Illinois 60506

March 31, 2014

VIA EDGAR

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.

Request for Acceleration of Effectiveness of

Registration Statement on Form S-1 (File No. 333-193424)

Ladies and Gentlemen:

Pursuant to Rule 461 under the Securities Act of 1933 (the “Securities Act”), Old Second Bancorp, Inc., a Delaware corporation (the “Company”), respectfully requests that the effective date of the above-referenced Registration Statement on Form S-1 be accelerated by the Securities and Exchange Commission (the “Commission”) so that the Registration Statement, as then amended, will become effective under the Securities Act at 1:00 p.m. (Eastern Standard Time) on Thursday, April 3, 2013, as soon as practicable thereafter or at such later time as the Company or its counsel may orally request via telephone call to the staff of the Commission.

The undersigned officer of the Company, on behalf of the Company, acknowledges that:

·                                    should the Commission or the staff, acting pursuant to delegated authority, declare the filing effective, it does not foreclose the Commission from taking any action with respect to the filing;

·                                    the action of the Commission or the staff, acting pursuant to delegated authority, in declaring the filing effective, does not relieve the Company from its full responsibility for the adequacy and accuracy of the disclosure in the filing; and

·                                    the Company may not assert staff comments and the declaration of effectiveness as a defense in any proceeding initiated by the Commission or any person under the federal securities laws of the United States.

We request that we be notified of such effectiveness by a telephone call to Robert M. Fleetwood at (312) 629-7329 or Gregory V. Demo at (312) 629-5182, both of Barack Ferrazzano Kirschbaum & Nagelberg LLP, and that such effectiveness also be confirmed in writing.

Very truly yours,

/s/ J. Douglas Cheatham

J. Douglas Cheatham

Executive Vice President and Chief Financial Officer

cc:

Mr. Robert M. Fleetwood

Mr. Gregory V. Demo

Barack Ferrazzano Kirschbaum & Nagelberg LLP

200 West Madison Street, Suite 3900

Chicago, Illinois 60606

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Keefe, Bruyette & Woods, Inc.

as representative of the several underwriters

787 Seventh Avenue

4th Floor

New York, New York 10019

March 31, 2014

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.
 Registration Statement on Form S-1
 Registration File No. 333-193424

Ladies and Gentlemen:

In accordance with Rule 461 of the Securities Act of 1933, as amended (the “Act”), we hereby join in the request of Old Second Bancorp, Inc. (the “Company”) for acceleration of the effective date of the above-named Registration Statement, as amended, so that it becomes effective at 1:00 p.m. (Washington, D.C. time) on Thursday, April 3, 2013, or as soon thereafter as practicable.

Pursuant to Rule 460 under the Act, we wish to advise you that we have effected distribution of 800 copies, in the aggregate, of the Company’s Preliminary Prospectus issued March 26, 2014 through the date hereof to prospective underwriters, institutions and others.

We have been informed by the participating underwriters that they will comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

Very   truly yours,

KEEFE,   BRUYETTE & WOODS, INC.

By:

/s/   Allen G. Laufenberg

Name:

Allen   G. Laufenberg

Title:

Managing   Director

2

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Confidential Treatment Requested by Old Second Bancorp, Inc., Pursuant to 17 C.F.R. § 200.83

March 26, 2014

VIA EDGAR

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:

Old Second Bancorp, Inc.

Amendment No. 1 to Registration   Statement on Form S-1

Filed February 27, 2014

File No. 333-193424

Form 10-K for Fiscal Year Ended

December 31, 2013

Filed February 26, 2014

File No. 000-10537

Dear Mr. Clampitt:

We are in receipt of your letter dated March 19, 2014, concerning the above-captioned filings of Old Second Bancorp, Inc. (the “Company”), and hereby submit the following responses to the comments contained therein.  To facilitate your review, we have repeated your comments below in bold italic type, followed by our responses.

The Company respectfully requests confidential treatment for certain omitted sections of this letter indicated by bracketed asterisks (“[***]”) below pursuant to 17 C.F.R. § 200.83 (“Rule 83”) promulgated by the Securities and Exchange Commission (the “Commission”).  Pursuant to Rule 83, the Company’s omitted responses will be provided to the Commission under separate cover in hard copy.  We request that these omitted sections be maintained in confidence, not be made part of any public record and not be disclosed to any person, because of the commercially sensitive nature of the omitted information.  In the event that the Commission receives a request for access to the confidential sections herein, whether pursuant to the Freedom of Information Act or otherwise, the Company respectfully requests that it be notified immediately so that it may further substantiate this request for confidential treatment under Rule 83.  Please address any notification of a request for access to such information to J. Douglas Cheatham, Old Second Bancorp, Inc., 37 S. River Street, Aurora, Illinois 60506.

Additionally, the Company has voluntarily enclosed with the paper copy of this letter supplemental materials responsive to the Commission’s comments on a confidential basis.  The supplemental information is being provided on a supplemental, confidential basis only and is not to be filed with or deemed a part of this response, pursuant to Rule 12b-4 under the Securities Exchange Act of 1934, as amended (“Rule 12b-4”).  Pursuant to Rule 12b-4, the Company hereby requests that the supplemental information be returned to the undersigned promptly following completion of the Commission’s review of the supplemental information.  In addition, in accordance with Rule 83, the Company requests confidential treatment due to the commercially sensitive nature of this information.

The Company has filed a separate letter with the Office of Freedom of Information and Privacy Act Operations in connection with the confidential treatment requests pursuant to Rule 83.

Amendment No. 1 to Registration Statement on Form S-1

Risk Factors, page 15

General

1.              We note your revised disclosure in response to prior comment 7 in our letter dated February 12, 2014.  However, your revised disclosure continues to discuss the possibility of risks that are currently unknown or appear immaterial.  Therefore, we reissue the comment.

In response to this comment, the Company has revised Amendment No. 2 to the Registration Statement on Form S-1 to remove the above-referenced language and undertakes to include this revised language, as appropriate, in future filings.

Form 10-K for the Fiscal Year Ended December 31, 2013

Item 8. Financial Statements and Supplementary Date

Note 11- Income Taxes, pages 104

2.              We note your response to comments 15 and 16 from our letter dated February 12, 2014. We note that you expect to utilize net operating losses before their expiration, starting in 2021 for Illinois NOLs and 2030 for federal NOLs. Please specifically provide your time horizon for the utilization of federal and state NOLs and provide detailed information addressing the future reversals and timing of existing taxable temporary differences

[***]

Item 13. Certain Relationships and Related Transactions..., page 156

3.              We note your disclosure in response to prior comment 14 in our letter dated February 12, 2014. With respect to the “certain transactions” between Alarm Detection Systems, Inc. and the Company, please revise future filings to provide the information required by Item 404(a) of Regulation S-K or tell us how you concluded that you are not required to do so.

In response to this comment, the Company undertakes to include the disclosure required by Item 404(a) of Regulation S-K, as appropriate, in future filings.

*  * * * *

The Company hereby acknowledges that:

·                  The Company is responsible for the adequacy and accuracy of the disclosure in the filings;

·                  Staff comments or changes to disclosure in response to Staff comments do not foreclose the Commission from taking any action with respect to the filing; and

2

·                  The Company may not assert Staff comments as a defense in any proceeding initiated by the Commission or any person under the federal securities laws of the United States.

The Company believes the foregoing provides a complete response to the Comment Letter.  If you have questions regarding the foregoing or require any additional information, please feel free to contact me directly at (630) 906-5484 or dcheatham@oldsecond.com or William Skoglund, Chairman and President of the Company, at (630) 906-5483 or wskoglund@oldsecond.com.

Sincerely,

/s/ J. Douglas Cheatham

J. Douglas Cheatham

Executive Vice President and Chief Financial   Officer

3

March 19, 2014

Via E -mail
William B. Skoglund
Chairman and Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60506

Re: Old Second Bancorp,  Inc.
Amendment No. 1 to  Registration Statement on Form S -1
Filed February  27, 2014
  File No. 333 -193424
Form 10 -K for Fiscal Year Ended
December 31, 2013
Filed February 26, 2014
File No. 000 -10537

Dear Mr. Skoglund :

We have reviewed the above referenced filings and have the following comments.  In
some of our comments, we may ask you to provide us with information so we may better
understand your disclosure.

Please respond to this letter by amending your registration statement and pr oviding the
requested information, including, if applicable, a draft of your proposed disclosures to be made
in future filings.  If you do not believe our comments apply to your facts and circumstances or do
not believe an amendment is appropriate, please tell us why in your response.

After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.

Amendment No. 1 to Registration Statement on Form S -1

Risk Fac tors, page 15

General

1. We note your revised disclosure in response to prior comment 7 in our letter dated
February 12, 2014.  However, your revised disclosure continues to discuss the possibility
of risks that are currently unknown or appear immaterial.  Therefore, we reissue the
comment.

William B. Skoglund
Old Second Bancorp, Inc.
March 19, 2014
Page 2

 Form 10 -K for the Fiscal Year Ended December 31, 2013

Item 8.  Financial Statements and Supplementary Data

Note 11 – Income Taxes, page 104

2. We note your response to comments 15 and 16 from our letter dated February 12 , 2014.
We note that you expect to utilize net operating losses before their expiration, starting in
2021 for Illinois NOLs and 2030 for federal NOLs.  Please specifically provide your time
horizon for the utilization of federal and state NOLs and provide  detailed information
addressing the future reversals and timing of existing taxable temporary differences.

Item 13. Certain Relationships and Related Transactions..., page 156

3. We note your disclosure in response to prior comment 14 in our letter dated F ebruary 12,
2014.  With respect to the “certain transactions” between Alarm Detection Systems,  Inc.
and the Company, please revise future filings to provide the information required by Item
404(a) of Regulation S -K or tell us how you concluded that you are  not required to do so.

We urge all persons who are responsible for the accuracy and adequacy of the disclosure
in the filing to be certain that the filing includes the information the Securities Act of 1933 and
all applicable Securities Act rules requi re.  Since the company and its management are in
possession of all facts relating to a company’s disclosure, they are responsible for the accuracy
and adequacy of the disclosures they have made.

Notwithstanding our comments, in the event you request acc eleration of the effective date
of the pending registration statement please provide a written statement from the company
acknowledging that:

 should the Commission or the staff, acting pursuant to delegated authority, declare the
filing effective, it does not foreclose the Commission from taking any action with respect
to the filing;

 the action of the Commission or the staff, acting pursuant t o delegated authority, in
declaring the filing effective, does not relieve the company from its full responsibility for
the adequacy and accuracy of the disclosure in the filing; and

 the company may not assert staff comments and the declaration of effect iveness as a
defense in any proceeding initiated by the Commission or any person under the federal
securities laws of the United States.

Please refer to Rules 460 and 461 regarding requests for acceleration.  We will consider a
written request for accele ration of the effective date of the registration statement as confirmation
of the fact that those requesting acceleration are aware of their respective responsibilities under

William B. Skoglund
Old Second Bancorp, Inc.
March 19, 2014
Page 3

 the Securities Act of 1933 and the Securities Exchange Act of 1934 as they relate  to the proposed
public offering of the securities specified in the above registration statement.  Please allow
adequate time for us to review any amendment prior to the requested effective date of the
registration statement.

You may contact Chris Ha rley at (202) 551 -3695 or David Irving at (202) 551 -3321  if
you have questions regarding comments on the financial statements and related matters.  Please
contact David Lin at (202) 551 -3552  or me at (202) 551 -3434  with any other questions.

Sincerely,

 /s/ Michael Clampitt

Michael Clampitt
Senior Counsel

cc: Via E -mail
 J. Douglas Cheatham
 Robert M. Fleetwood , Esq.

CORRESP
1
filename1.htm

Confidential Treatment Requested by Old Second Bancorp, Inc., Pursuant to 17 C.F.R. § 200.83

February 27, 2014

VIA EDGAR

Securities Exchange Commission

Division of Corporate Finance

U.S. Securities and Exchange Commission

100 F Street, NE

Washington, D.C. 20549

Attention:  Michael Clampitt

Re:                             Old Second Bancorp, Inc.

Registration Statement on Form S-1

Filed January 17, 2014

File No. 333-193424

Form 10-K for Fiscal Year Ended

December 31, 2012

Filed March 20, 2013

Form 10-Q for Fiscal Quarter Ended

September 30, 2013

Filed November 12, 2013

File No. 000-10537

Dear Mr. Clampitt:

We are in receipt of your letter dated February 12, 2014, concerning the above-captioned filings of Old Second Bancorp, Inc. (the “Company”), and hereby submit the following responses to the comments contained therein.  To facilitate your review, we have repeated your comments below in bold italic type, followed by our responses.

The Company respectfully requests confidential treatment for certain omitted sections of this letter indicated by bracketed asterisks (“[***]”) below pursuant to 17 C.F.R. § 200.83 (“Rule 83”) promulgated by the Securities and Exchange Commission (the “Commission”).  Pursuant to Rule 83, the Company’s omitted responses will be provided to the Commission under separate cover in hard copy.  We request that these omitted sections be maintained in confidence, not be made part of any public record and not be disclosed to any person, because of the commercially sensitive nature of the omitted information.  In the event that the Commission receives a request for access to the confidential sections herein, whether pursuant to the Freedom of Information Act or otherwise, the Company respectfully requests that it be notified immediately so that it may further substantiate this request for confidential treatment under Rule 83.  Please address any notification of a request for access to such information to J. Douglas Cheatham, Old Second Bancorp, Inc., 37 S. River Street, Aurora, Illinois 60506.

Additionally, the Company has voluntarily enclosed with the paper copy of this letter supplemental materials responsive to the Commission’s comments on a confidential basis.  The supplemental information is being provided on a supplemental, confidential basis only and is not to be filed with or deemed a part of this response, pursuant to Rule 12b-4 under the Securities Exchange Act of 1934, as amended (“Rule 12b-4”).  Pursuant to Rule 12b-4, the Company hereby requests that the supplemental information be returned to the undersigned promptly following completion of the Commission’s review

of the supplemental information.  In addition, in accordance with Rule 83, the Company requests confidential treatment due to the commercially sensitive nature of this information.

The Company has filed a separate letter with the Office of Freedom of Information and Privacy Act Operations in connection with the confidential treatment requests pursuant to Rule 83.

Registration Statement on Form S-1

General

1.              Please revise to include executive compensation disclosure for your completed fiscal year ended December 31, 2013. For guidance, refer to Regulation S-K Compliance and Disclosure Interpretation 217.11, available on the SEC website.

The Company has included in its Form 10-K for the year ended December 31, 2013, which was filed with the Commission on February 26, 2014, the required executive compensation disclosure for the fiscal year ended December 31, 2013, and has incorporated such disclosure by reference into Amendment No. 1 to the Registration Statement on Form S-1 (the “Amendment”).

2.              Please provide the disclosure required by Item 505 of Regulation S-K or advise.

The Company respectfully submits that it is not required to provide the disclosure required by Item 505 of Regulation S-K.  The Company’s common stock is listed on The Nasdaq Global Select Market and actively traded.  Further, the Company does not believe that there will be any material disparity between the price of its common stock in its public offering and the market price of its common stock listed on The Nasdaq Global Select Market although the Company does expect that the price of its common stock in the public offering will be slightly lower than the market price.  Consequently, the Company is not required to provide the disclosure required by Item 505(a) of Regulation S-K.  Moreover, since the Company is only registering common stock, it is also not required to provide the disclosure required by Item 505(b) of Regulation S-K.

Cover Page of Prospectus

3.              Please confirm that you will disclose the number of shares of common stock being offered in an amendment filed prior to any distribution of the prospectus.

The Company will disclose the number of shares of common stock being offered in an amendment filed prior to any distribution of the prospectus.

Incorporation by Reference, page 3

4.              Revise to update this section through the latest practicable date.

The Company has updated this section in the Amendment through and including the date of the Amendment.

2

Selected Financial Date, page 12

5.              Please revise future filings, starting with the December 31, 2013 10-K, to reflect the line items titled ‘Lease revenue from other real estate owned’ and ‘Net gain on sale of other real estate owned’ in the net cost of operation of other real estate (including provisions for real estate losses, rental income and gains and losses on sales of real estate) within Noninterest Expenses on the Consolidated Statement of Operations pursuant to Rule 9-04 (14) (d) of Regulation S-X. In addition, revise the MD&A discussion in future filings as well.

The Company has included the information requested in this Comment 5 in its Form 10-K for the year ended December 31, 2013, which was filed with the Commission on February 26, 2014, and undertakes to include this information, as appropriate, in future filings.

6.              Revise the line item titled net loans charged off to average total loans to reflect annualized amounts as of the nine months ended September 30, 2013 and 2012 and provide a note to state that these amounts have been annualized.

The Company has revised the selected financial data in the Amendment to include financial data as of the year ended December 31, 2013, and consequently is no longer providing the data referenced in this Comment 6.

Risk Factors, page 15

General

7.              We note that the introductory paragraph discusses the possibility of risks that are currently unknown or appear immaterial. Please revise to delete this language, which is unnecessarily confusing.

In response to this comment, the Company has revised the Amendment to remove the confusing language.

Our business is concentrated in and dependent upon...page 17

8.              We note your disclosure that “the State of Illinois’s financial condition continues to be among the most troubled of any state in the United States.” Please revise to provide more detailed information, including quantification to the extent feasible, as to the unemployment rate, mortgage delinquencies, real estate price declines, or other similar indicators, for your primary market area.

In response to this comment, the Company has revised the Amendment to provide more detailed information concerning the troubled financial condition of the State of Illinois, namely that Illinois ranks in the bottom ten states in the United States of America both in terms of unemployment and foreclosure rates.

3

The holders of our senior preferred stock..., page 27

9.              Revise to disclose the current holder(s) of the warrant, the exercise terms and the date of expiration of the warrant.

The Company has revised the Amendment to disclose the exercise price and expiration date of the warrant to purchase 815,339 shares of Company common stock.  The Company respectfully submits that disclosure of the current holder of the warrant is not required.  Item 403 of Regulation S-K only requires the disclosure of persons or entities that beneficially own five percent or more of any class of a registrant’s voting securities or who are directors or executive officers of a registrant.  The current holder of the warrant is an unrelated third party that does not beneficially own or hold, even assuming the warrant were to be fully exercised, five percent or more of the Company’s voting securities.

Underwriting

Director and Officer Participation, page 43

10.       We note that the underwriters will reserve a certain percentage of the shares for sale directly to your directors and officers. Please describe the mechanics of how and when these shares are offered and sold to investors in the directed share program for this offering. For example, tell us how the prospective recipients and number of reserved shares are determined. Tell us how and when the issuer and underwriter notified the directed share investors, including the types of communications used. Discuss the procedures these investors must follow in order to purchase the offered securities. Are directed share purchasers required to establish accounts before the effective time, and, if so, what if any funds are put in newly established brokerage accounts before the effective date? How do the procedures for the directed share program differ from the procedures for the general offering to the public?

The Company has replaced the disclosure about the directed share program with a statement that  all of the Company’s directors and certain of its officers intend to purchase shares of Company common stock in the offering from the underwriters.  Based on their indications of interest, the Company’s directors and certain of its officers intend to subscribe for approximately $1.3 million worth of shares of common stock in this offering.  All of the terms and conditions of the purchases by these directors and officers will be the same as any other person in the general offering to the public, including the purchase price, except that the underwriters will reserve these shares specifically for purchase by these directors and officers.  No special documentation will be prepared in connection with offers to the Company’s directors and officers, and the directors and officers will receive the same offering materials as are distributed to the general public.  Any directors and officers who do not have existing accounts with an underwriter or selling group member, or an investment account with the Company, will be required to open an account with an underwriter.  After the registration statement is declared effective and pricing occurs, the directors and officers will receive confirmations of their purchases from the underwriters and will wire transfer or send checks to their accounts for the purchase price.  Their shares will settle in the same manner as the shares sold to any other retail investor.

Part II

11.       We are unable to locate the information required by Item 15 of Part II of Form S-1.  Please revise or advise, as appropriate.

The Company respectfully submits that the information required by Item 15 of Part II of Form S-1 is not required as the Company has not sold any securities within the last three years which were not registered under the Securities Act of 1933.

4

Exhibits

12.       Refer to the last sentence on page 1 of the legality opinion filed as Exhibit 5.1. We note that counsel expresses “no opinion regarding the statutes, administrative decisions, rules, regulations or requirements of any county, municipality, subdivision or local authority or any jurisdiction.” (Emphasis added.) This limitation appears to be overly broad, insofar as it would include the “federal law of the United States of America and the General Corporation Law of the State of Delaware,” as set forth in the preceding sentence. Please advise or revise as appropriate.

In response to this Comment, the Company’s attorneys have revised their legal opinion filed as Exhibit 5.1 to the Amendment to clarify that their legal opinion applies to the federal laws of the United States of America and the General Corporation Law of the State of Delaware.

13.       Please file the following as exhibits with your next amendment:

·                  engagement letter, as amended and restated on November 15, 2013, between the Company and Keefe, Bruyette & Woods, Inc.; and

·                  2013 non-equity incentive compensation plan.

Alternatively, please provide us with an analysis supporting your determination that they are not required to be filed pursuant to Item 601 of Regulation S-K.

The Company respectfully submits that the engagement letter (the “engagement letter”) with Keefe, Bruyette & Woods, Inc. (“KBW”) is not a document that is required to be filed as an exhibit to the registration statement pursuant to Item 601 of Regulation S-K.  The engagement letter is not an underwriting contract or agreement with a principal underwriter that would be required to be filed pursuant to Item 601(b)(1) of Regulation S-K.  The underwriting agreement is the agreement that will contain all of the terms of the underwriting arrangements between KBW and the Company for this offering, a form of which was filed as an exhibit to the registration statement.

The engagement letter is also not a contract material to the Company that would be required to be filed pursuant to Item 601(b)(10)(i) of Regulation S-K.  The Company does not believe that there is any information in the engagement letter that is material to an understanding of the Company’s business.  In addition, the Company and KBW intend to revise the engagement letter to remove the right of first refusal that was originally contained therein and have deleted the corresponding disclosure from the Amendment.  The selection of KBW as a financial advisor or lead underwriter for a potential offering is not material to the Company.  It is customary for companies to select investment banks to serve as financial advisors or lead underwriters for potential financings from time to time.  The selection of an investment bank is not material or required to be disclosed until the time an offering is undertaken, at which time the terms of the underwriting agreement are negotiated between the parties and described in the prospectus.  All of the material terms of the underwriting agreement between KBW and the Company are described in the prospectus.  In addition, the Company believes that the filing of the engagement letter would not provide any additional information that is material to investors.

The Company has not adopted a 2013 non-equity incentive plan.  The 2013 non-equity incentive plan referenced in the Company’s proxy statement for its 2013 annual meeting filed on April 15, 2013, with the Commission on Schedule 14A refers to certain performance metrics adopted by the Company’s Compensation Committee rather than a formal plan capable of being filed with the Commission.

5

Form 10-K for the Fiscal Year Ended December 31, 2012

Item 13. Certain Relationships and Related Transactions..., page 128

14.       We note your incorporation by reference of the information required by Item 13 from your DEF 14A filed April 15, 2013, including, without limitation, the section headed “Transactions with Management”. However, we are unable to locate such disclosure in the DEF 14A. Please revise to include the information required by Item 404 of Regulation S-K, or confirm that no disclosure is required.

The Company has included the information required by Item 404 of Regulation S-K in Item 13 of the Company’s Form 10-K for the year ended December 31, 2013, which was filed with the Commission on February 26, 2014, and has incorporated this disclosure by reference into the Amendment.

Form 10-Q for the Fiscal Quarter E

February 12, 2014

Via E -mail
William B. Skoglund
Chairman and Chief Executive Officer
Old Second Bancorp, Inc.
37 South River Street
Aurora, IL 60506

Re: Old Second Bancorp,  Inc.
Registration Statement on Form S -1
Filed January 17, 2014
  File No. 333 -193424
Form 10 -K for Fiscal Year Ended
December 31, 2012
Filed March 20, 2013
Form 10 -Q for Fiscal Quarter Ended
September 30, 2013
Filed November 12, 2013
File No. 000 -10537

Dear Mr. Skoglund :

We have reviewed the above referenced filings and have the following comments.  In
some of our comments, we may ask you to provide us with information so we may better
understand your disclosure.

Please respond to this letter by amending your registration statement and providing the
requested information, including, if applicable, a draft of your proposed disclosures to be made
in future filings.  If you do not believe our comments apply to your fa cts and circumstances or do
not believe an amendment is appropriate, please tell us why in your response.

After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.

Registration Statement on Form S -1

General

1. Please revise to include executive compensation disclosure for your completed fiscal year
ended December 31, 2013.  For guidance, refer to Regulation S -K Compliance
and Disclosure Interpretation 217 .11, available on the SEC website.

William B. Skoglund
Old Second Bancorp, Inc.
February 12, 2014
Page 2

 2. Please provide the disclosure required by  Item 505  of Regulation S -K or advise.

Cover Page of Prospectus

3. Please confirm that you will disclose the number of shares of common stock being
offered in an amendment filed prior to any distribution of the prospectus.

Incorporation by Reference, page 3

4. Revise to update this section through the latest practicable date.

Selected Financial Data, page 12

5. Please r evise future filings, starting with the December 31, 2013 10 -K, to reflect the line
items titled ‘Lease revenue from other real estate owned ’ and ‘Net gain on sale of other
real estate owned ’ in the net cost of operation of other real estate (including provisions
for real estate losses, rental income and gains and loss es on sales of real estate) within
Noninterest E xpenses on the Consolidated Statement of Operations pursuant to Rule 9 -04
(14) (d) of Regulation S -X.  In addition, revise the MD&A discussion in future filings as
well.

6. Revise the line item titled net loans  charged off to average total loans to reflect
annualized amounts as of the nine months ended September 30, 2013 and 2012 and
provide a note to state that these amounts have been annualized.

Risk Factors, page 15

General

7. We note that the introductory pa ragraph discusses the possibility of risks that are
currently unknown or appear immaterial.  Please revise to delete this language, which is
unnecessarily confusing.

Our business is concentrated in and dependent upon...page 17

8. We note your disclosure that “ the State of Illinois’s financial condition continues to be
among the most troubled of any state in the United States.”  Please revise to provide more
detailed information, including quantification to the extent feasible, as to the
unemployment rate, mortgage delinquencies, real estate price declines, or other similar
indicators, for your primary market area.

William B. Skoglund
Old Second Bancorp, Inc.
February 12, 2014
Page 3

 The holders of our senior preferred stock…, page 27

9. Revise to disclose the current holder(s) of the warrant, the exercise terms and the date of
expiration of the warrant.

Underwriting

Director and Officer Participation, page 43

10. We note that the underwriters will r eserve a certain percentage of the shares for sale
directly to your directors and officers.  Please describe the mechanics of how and when
these shares are offered and sold to investors in the directed share program for this
offering.  For example, tell us  how the prospective recipients and number of reserved
shares are determined.  Tell us how and when the issuer and underwriter notified the
directed share investors, including the types of communications used.  Discuss the
procedures these investors must f ollow in order to purchase the offered securities.  Are
directed share purchasers required to establish accounts before the effective time, and, if
so, what if any funds are put in newly established brokerage accounts before the effective
date?  How do the  procedures for the directed share program differ from the procedures
for the general offering to the public?

Part II

11. We are unable to locate the information required by Item 15 of Part II of Form S -1.
Please revise or advise, as appropriate.

Exhibit s

12. Refer to the last sentence on page 1 of the legality opinion filed as Exhibit 5.1.  We note
that counsel expresses “no opinion regarding the statutes, administrative decisions, rules,
regulations or requirements of any county, municipality, subdivision or local authority or
any jurisdiction .” (Emphasis added.)  This limitation appears to be overly broad, insofar
as it would include the “federal law of the United States of America and the General
Corporation Law of the State of Delaware,” as set forth in the preceding sentence.  Please
advise or revise as appropriate.

13. Please file the following as exhibits with your next amendment:
 engagement letter, as amended and restated on November  15, 2013, between the
Company and Keefe, Bruyette  & Woods,  Inc.; and
 2013 non -equity incentive compensation plan.
Alternatively, please provide us with an analysis supporting your determination that they are
not required to be filed pursuant to Item 601 of Regulation S -K.

William B. Skoglund
Old Second Bancorp, Inc.
February 12, 2014
Page 4

 Form 10 -K for the Fiscal Year Ended December 31, 2012

Item 13. Certain Relationships and Related Transactions..., page 128

14. We note your incorporation by reference of the information required by Item 13 from
your DEF 14A filed April  15, 2013, including, without limitation, the section headed
“Transactio ns with Management”.  However, we are unable to locate such disclosure in
the DEF 14A.  Please revise to include the  information required by Item 404  of
Regulation S -K, or confirm that no disclosure is required.

Form 10 -Q for the Fiscal Quarter Ended  September 30, 2013

Item 1.  Financial Statements

Note 16 – Income Taxes, page 39

15. We note you released a large portion of the deferred tax asset valuation allowance during
the interim period of September 30, 2013.   We note that you recognized significant
cumulative losses before taxes during the fiscal 2008 -2012 periods.   In determining the
need for a valuation allowance, forming a conclusion that a valuation allowance is not
necessary is difficult when there is negative evidence such as cumulative losses fro m
continuing operations, which is considered a significant piece of negative evidence that is
difficult to overcome (refer to paragraphs 21 – 23 of ASC 740 -10-30).   Furthermore the
weight given to the potential effect of negative and positive evidence sho uld be
commensurate with the extent to which it can be objectively verified, specifically
concerning forecasts of future taxable income.  Please provide us with the following
specific evidence to support the realizability of the net deferred tax asset at S eptember 30,
2013:

 Specific detailed information to support the realizability of the net deferred tax asset
at September 30, 2013;
 Forecasted projections utilized at September 30, 2013, including all assumptions
considered.  In regard to any projections and assumptions utilized, provide us with
specific evidence to support the assumptions such as the number of years in the
projections, estimated growth rates, net interest margins considered, estimated loan
loss provision rates as well as reven ue and expense growth rates utilized;
 Detailed information comparing actual versus forecasted results for the fiscal years
ended December 31, 2012 and the nine month period ended September 30, 2013;
 Specific information related to tax -planning strategies and how you considered the
guidance in ASC 740 -10-30-20 to support the how you determined you could
generate $11.4 million of taxable income from the sale of bank -owned life insurance;
and
 Please update to provide your analysis for the 3 - and 12 -months end ed December 31,
2013, if available.

William B. Skoglund
Old Second Bancorp, Inc.
February 12, 2014
Page 5

16. Please explain to us how you considered the following in support of management’s
decision to reverse most of the deferred tax asset valuation allowance during the periods
presented:

 The magnitude and duration of your past losses as well as your return to profitability;
 The significant factors driving your past losses and the current profitability; and
 The sustainability of your current profitability in light of the current economic
environment.

We urge all persons who are responsible for the accuracy and adequacy of the disclosure
in the filing to be certain that the filing includes the information the Securities Act of 1933 and
all applicable Securities Act rules require.   Since the company and its management are in
possession of all facts relating to a company’s disclosure, they are responsible for the accuracy
and adequacy of the disclosures they have made.

Notwithstanding our comments, in the event you request acceleration of the effective date
of the pending registration statement please provide a written statement from the company
acknowledging that:

 should the Commission or the staff, acting pursuant to delegated authority, declare the
filing effective, it does not foreclose the Commissi on from taking any action with respect
to the filing;

 the action of the Commission or the staff, acting pursuant to delegated authority, in
declaring the filing effective, does not relieve the company from its full responsibility for
the adequacy and accuracy of the disclosure in the filing; and

 the company  may not assert staff comments and the declaration of effectiveness as a
defense in any proceeding initiated by the Commission or any person under the federal
securities laws of the United States.

Please refer to Rules 460 and 461 regarding requests for acceleration.  We will consider a
written request for acceleration of the effective date of the registration statement as confirmation
of the fact that those requesting acceleration are aware of their respective responsibilities under
the Securities Act of  1933 and the Securities Exchange Act of 1934 as they relate to the proposed
public offering of the securities specified in the above registration statement.  Please allow
adequate time for us to review any amendment prior to the requested effective date o f the
registration statement.

William B. Skoglund
Old Second Bancorp, Inc.
February 12, 2014
Page 6

 You may contact Chris Harley at (202) 551 -3695 or David Irving at (202) 551 -3321  if
you have questions regarding comments on the financial statements and related matters.  Please
contact David Lin at (202) 551 -3552  or me  at (202) 551 -3434  with any other questions.

Sincerely,

 /s/ Michael Clampitt

Michael Clampitt
Senior Counsel

cc: Via E -mail
 J. Douglas Cheatham
 Robert M. Fleetwood , Esq.

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

      DIVISION OF
CORPORATION FINANCE
Mail Stop 4720
        July 6, 2009
By U.S. Mail and Facsimile to: (630) 906-3208

J. Douglas Cheatham Executive Vice President and Chief Financial Officer Old Second Bancorp, Inc. 37 South River Street Aurora, Illinois 60507

Re: Old Second Bancorp, Inc.
 Form 10-K for the Fiscal Year Ended December 31, 2008
 Filed March 16, 2009
 File No. 000-10537

Dear Mr. Cheatham:

We have completed our review of your Form 10-K and related filings and have no further
comments at this time.

Sincerely,

Christian Windsor Special Counsel

CORRESP
1
filename1.htm

May 20, 2009

VIA
EDGAR

Securities and Exchange
Commission

Division of Corporate Finance

100 F Street, N.E.

Mail Stop 4561

Washington, DC 20549-0408

Attention:  Mr. Christian Windsor

  Re:

  Old Second Bancorp, Inc.

  Form 10-K for the Fiscal
  Year Ended December 31, 2008

  (Filed March 16, 2009)

  Form 8-K (Filed
  April 21, 2009)

  File No. 000-10537

Dear Mr. Windsor:

Old Second Bancorp, Inc.
(the “Company”) has filed via EDGAR today its responses to the comments of the
Staff contained in a letter, dated April 27, 2009, relating to the
above-referenced filings.  Set forth
below are the comments contained in the Staff’s letter and immediately below
each comment is the response with respect thereto.

Form 10-K for the Fiscal
Year Ended December 31, 2008

Item 5.
Market for the Registrant’s Common Equity…..page 29

1.                    It does not appear that the
company included a performance graph in its 2008 annual report to security
holders.  Please provide us with the
performance graph and confirm that the company will provide the performance
graph to security holders in accordance with Item 201(e) of Regulation S-K
in future filings.

The Company’s response is
as follows:

The 2008 performance
graph is included immediately below as part of this response.  The Company also confirms that it will
provide the requisite performance graph to security holders in accordance with
Item 201(e) of Regulation S-K in its future filings.

  Date

  Old Second

  Bancorp

  NASDAQ Bank

  Index

  S&P 500

  December 31, 2003

  $100.00

  $100.00

  $100.00

  December 31, 2004

  $130.95

  $113.62

  $110.85

  December 31, 2005

  $127.72

  $111.44

  $116.28

  December 31, 2006

  $124.62

  $126.79

  $134.61

  December 31, 2007

  $116.37

  $101.60

  $141.99

  December 31, 2008

  $52.53

  $79.80

  $89.54

Item 10.
Directors, Executive Officers, and Corporate Governance, page 32

2.                    Please revise to describe the
business experience, including principal occupations and employment, of Mr. Sloan
during the past five years.  Refer to
Item 401(e) of Regulation S-K.

The Company’s response is
as follows:

During the past
five years, Mr. Sloan has served as Senior Vice President and Senior
Lending Officer for Old Second Bancorp, Inc.  In 2007, he assumed the title of Executive
Vice President, Chief Risk Officer, taking on additional responsibility for
overall Enterprise Risk Management for the Company.   This is reflected in
the draft amendment to Form 10-K attached as Exhibit A to this letter.

Item 11. Executive Compensation, page 32

General

3.                   You state that the sections in
the proxy statement marked “Executive Compensation”, “Director Compensation”, “Compensation
Discussion and Analysis” and “Compensation Committee Report” are furnished for
the information of the Commission and are not deemed “filed” as part of the Form 10-K.  Other than the information required by Item
407(e)(5) of Regulation S-K, all of the information you reference is
filed, and not furnished.  Please file an
amendment to the Form 10-K confirming that these sections, other than the
Compensation Committee Report, are incorporated into the Form 10-K and are
deemed filed, or provide the information required by Part III of Form 10-K.  Please also confirm that you will revise your
future filings accordingly.

The Company’s response is as follows:

Please refer to Exhibit A
for a draft amendment to Form 10-K for the fiscal year ending December 31,
2008.  The purpose of the amendment is to make it clear that the sections
of the Company’s proxy statement entitled “Executive Compensation”, “Director Compensation”,
and “Compensation Discussion and Analysis” are incorporated by reference into
the Form 10-K and are deemed filed as part of the Form 10-K and
not deemed to be furnished.  The Company will make this clear in its
future filings.

Compensation Discussion and Analysis, page 12
of Definitive Proxy Statement

4.                   We note that the company
benchmarks certain elements of compensation to its peers.  Please identify, and revise future filings to
disclose, the component companies that make up the compensation peer group(s) and
the basis for selecting the peer group(s).
Refer to Item 402(b)(2)(xiv) of Regulation S-K.

The Company’s response is as follows:

As disclosed in the proxy
statement, for several years, the Compensation Committee has utilized the services
of an outside consultant for expertise and resources regarding current market
activities and to assist the committee in benchmarking and comparing the
Company’s compensation and benefit programs with an objective peer group.”  The peer group utilized in 2008 included
various Midwest banks.  The committee
believed that this was appropriate peer group because of the similar size,
location and complexity between the peers and the Company.  The peer group consists of:

  1st Source Corp

  AMCORE Financial, Inc.

  Capital Bancorp Ltd.

  Centrue Financial Group

  First Financial Corp.

  Firstbank Corp.

  Integra Bank Corp

  Macatawa Bank Corp.

  MBT Financial Corp.

  Mercantile Bancorp, Inc.

  Midwest Bank Holdings, Inc.

  Private Bancorp, Inc.

  QCR Holdings, Inc.

  Taylor Capital Group

For future filings, the
component peer group will be disclosed.

Individual
Goals Component, page 18 of Definitive Proxy Statement

5.                   Please tell us why you have not
disclosed certain of the performance targets utilized in determining annual
bonus compensation for your named executive officers for the 2008 fiscal
year.  For example, you have not
disclosed the specific targets for return on equity, efficiency ratio, total
net charge-offs, net interest margin and total loan growth that were used as
bases for determining the individual component of the annual bonuses for your
named executive officers.  To the extent
you believe that disclosure of the historical performance targets is not
required because it would result in competitive harm such that the targets
could be excluded under Instruction 4 to Item 402(b) of Regulation S-K,
please provide a detailed supplemental analysis supporting your
conclusion.  In particular, your
competitive harm analysis should clearly explain the nexus between disclosure
of the performance objectives and the competitive harm that is likely to result
from disclosure.  Refer to Item 402(b)(2)(v) of
Regulation S-K and Regulation S-K Compliance and Disclosure Interpretation
118.04.

The Company’s response is
as follows:

As set forth in the proxy
statement for 2008, individual goals were assigned to each officer and
generally reflected measures that are affected by that officer’s
performance.  The measures used by the
committee include return on equity, our efficiency ratio, total net
charge-offs, growth in earnings per share (“EPS”), and the goals varied from
officer to officer.  The Company did not
believe it was necessary to provide the specific performance targets for the
individual goals, but will revise future filings to include such information.  The following is a description of the
individual performance targets for 2008:

EPS Growth vs. Peer; ROE
vs. Peer (two-year average)

Peer group:  publicly traded Midwest banks with assets of
$1-$5 billion.

  Peer Comparison

  Percent of
  Allocation Factor

  75th Percentile +

  125%

  62.5th Percentile

  100%

  40th Percentile

  50%

  Below 40th Percentile

  0%

Efficiency ratio goal:  62 % or lower

Net charge-off goal:

  Charge-off percentage

  Percent of Allocation Factor

  0.05% or less

  125%

  0.75%

  100%

  0.10%

  75%

Item
13.  Certain Relationships and Related
Transactions…page 33

Transactions
with Management, page 35 of Definitive Proxy Statement

6.                   We note the disclosure on pages 35-36
of your definite proxy statement that the loans were made on substantially the
same terms as those prevailing at the time for comparable transactions with
other persons.  Please confirm, and
revise future filings to disclose, if true, that the loans were made on substantially
the same terms, including interest rates and collateral, as those prevailing at
the time for comparable loans with persons not related to the lender.  Refer to Instruction 4(c) to Item 404(a) of
Regulation S-K.

The Company’s response is
as follows:

The Company confirms that
the loans referred to under “Certain Relationships and Related Transactions”
and “Transactions with Management” in the proxy statement were made on
substantially the same terms, including interest rates and collateral, as those
prevailing at the time for comparable loans with persons not related to the
lender.  The Company will disclose this
in its future filings.

Signatures.
Page 36

7.                   Please tell us if the report has
been signed by the company’s controller or principal accounting officer.  Refer to General Instruction D(2)(a) to Form 10-K.

The Company’s response is
as follows:

The Company’s Chief
Financial Officer is also its principal accounting officer and, therefore, it
was signed in accordance with the general instruction cited above.  In future filings, the Company will provide a
specific notation to the principal accounting officer on the signature page.

Management’s
Discussion and Analysis, page 48

8.                   We note your disclosure that
approximately $53.6 million of the problem loan total was acquired through the
Heritage Bank acquisition.  Further, we
note you carried over approximately $3.0 million of allowance related to the
loans acquired from Heritage Bank.
Please tell us how you considered whether any of the acquired loans were
within the scope of SOP 03-3 on the acquisition date.  To the extent that you are accounting for
some of the

acquired loans under SOP 03-3, please review your
future filings to more clearly reflect that fact.

The Company’s response is
as follows:

While the Company may
have used terminology that suggested SOP 03-3 might have been applicable, the
Company did not buy any loans at a significant discount, and accordingly
management does not believe that SOP 03-3 applied.  As such, the business combination with
Heritage was accounted for under the purchase method of accounting, FASB
Statement No. 141, as disclosed in the Company’s filings.

Notes to Consolidated Financial
Statements

Note D; Securities, page 76

9.                   We note the significant unrealized
losses related to your collateralized debt obligations (backed by trust
preferred securities) at December 31, 2008.  We have the following comments:

·                                          Please provide us a detailed
analysis of the securities’ impairment as of December 31, 2008 that identifies
all available evidence, explains the relative significance of each piece of
evidence, and identifies the primary evidence on which you rely to support a
realizable value equal to or greater than the carrying value of the investment.  Specifically tell us if you considered all
available evidence, including information received after year end, affecting
the projected cash flows as of the period end.
We may have further comment based on your response.

·                                          Please provide us with, and
consider disclosing in future filings, a table detailing the following
information for these securities: deal name, single-issuer or pooled, class,
book value, fair value, unrealized gain/loss, credit ratings, number of banks in
issuance, deferrals and defaults as a dollar amount and percentage of
collateral, and excess subordination.

The Company’s response is
as follows:

Point 1:

Management’s
procedures to assess impairment included the performance of both an initial and
follow up review to include all the available evidence, including information
that became available after year-end.
Evidence such as a decline in credit ratings, announced deferments and
defaults, and other items that affect the projected cash flows was taken into
consideration to support management’s assessment that the realizable value of
the securities was greater than the carrying value of the investments at the
reporting date.

These securities were rated AAA at acquisition and after acquisition,
management’s analysis was used to determine whether impairment was temporary or
other than temporary, considering the below factors:

·                  Probability
of collecting all amounts due according to the contractual terms of the debt
security based upon the results of stressed cash flow analyses, which shows all
principal and interest being paid as agreed.

·                  Severity
of impairment, including the duration period, which was relatively short.

·                  The
issuer’s financial condition and near-term prospects were considered to be
good, and;

·                  Management
intent and ability to hold these securities.

The
credit update and related cash flow analysis of the underlying institutions in
the CDO obligation provided primary support that the realizable value of the
securities was greater than the carrying value of the investment and that the
debt securities would pay as agreed even under a high stress scenario.  Each underlying institution was analyzed
individually for deferment or failure potential under continued and
progressively heightened stressed economic scenarios and the cash flow impact
of projected deferment or failure was included in the cash flow scenarios analyzed.  The cash flow analysis scenarios were
prepared by a third party agent, and a detailed review of the likely results
was performed by management who is responsible for interpreting the cash flow
analysis.

The
analysis for potential deferment or failure for each institution relied on an
overall knowledge of financial analysis plus specific knowledge related to the
performance of the underlying institutions.
The degree of risk was weighted to each underlying institution and
included an analysis of several key ratios and trends in those ratios.  Key ratios analyzed were non-performing
assets to tangible capital and reserves nonperforming assets to total assets
and tangible capital ratio.  In addition,
the institution’s profitability was also a key performance actor.  A cease and desist announcement from the
institution’s primary regulator affects the stressed cash flow analysis by
accelerating the estimate of failure date (unless a recapitalization plan
accompanied the regulatory declaration).

Secondary
factors that were taken into consideration included the following:  the location of the institutions primary
markets and the health of that market, and the relative concentration of loans
in real estate development and commercial real estate.  If an institution exhibited stress in the
above ratio analysis, then the level of core deposits to total deposits, and
the amount of reliance on brokered deposits, as well as the related trends in
those areas were analyzed.  Public
company announcements, including management action plans, were also
reviewed.  Announcements that would allow
companies to build capital (such as the decrease or the elimination of common
stock dividends) were noted.

Although
some institutions were downgraded to a higher degree of risk than the prior
analysis due to continued credit deterioration observed at year end or in the
period prior to filing the 10-K, the stress cash flow analysis still supported
repayment per original terms.  Two
institutions were upgraded due to capital injections from existing shareholders
and one from a new shareholder who took control of the institution.  One institution was acquired and the new bank’s
financial results were reviewed as part of the credit and cash flow analysis
update.

Point 2:

The
Company considered the tabular disclosure request cited above and included the
requested information in its May 11, 2009 filing of the March 31,
2009 10-

CORRESP
1
filename1.htm

OLD
SECOND BANCORP, INC.

April 29, 2009

VIA
EDGAR

Securities and
Exchange Commission

Division of
Corporation Finance

450 Fifth Street,
N.W.

Mail Stop 4561

Washington,
D.C.  20549-0408

Attention:  Mr. Justin Dobbie

RE:         Old
Second Bancorp, Inc.

        Form 10-K for the fiscal year ended
December 31, 2008 (filed March 16, 2009)

        Form 8-K (filed April 21,
2009)

        File No. 000-10537

Dear Mr. Dobbie:

Please allow this letter to serve as Old Second
Bancorp, Inc.’s (“Old Second”) request for additional time to respond to
the comments of the Staff contained in a letter, dated April 27, 2009,
relating to the above-referenced filings.
Old Second is currently working with its independent public accountants
and legal counsel to respond to the April 27 letter and will provide a
complete written response as required no later than May 21, 2009.

Please do not hesitate to call me if
you have any questions regarding this response.

  Very truly
  yours,

  /s/ J. Douglas
  Cheatham

  J. Douglas
  Cheatham

  Executive Vice
  President and

  Chief Financial
  Officer

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

       DIVISION OF
CORPORATION FINANCE
Mail Stop 4561
April 27, 2009

By U.S. Mail and Facsimile to: (630) 906-3208

J. Douglas Cheatham Executive Vice President and Chief Financial Officer Old Second Bancorp, Inc. 37 South River Street Aurora, Illinois 60507

Re: Old Second Bancorp, Inc.
Form 10-K for the Fiscal Year Ended December 31, 2008
(Filed March 16, 2009)
Form 8-K (Filed April 21, 2009)
 File No. 000-10537

Dear Mr. Cheatham:

We have reviewed your filing and have the following comments.  Where
indicated, we think you should re vise your document in response to these comments.  If
you disagree, we will consider your explanation as to why our comment is inapplicable or
a revision is unnecessary.  Please be as deta iled as necessary in your explanation.  In
some of our comments, we may ask you to provi de us with information so we may better
understand your disclosure.  After reviewing th is information, we may raise additional
comments.   Please understand that the purpose of our re view process is to assist you in your
compliance with the applicable disclosure  requirements and to  enhance the overall
disclosure in your filing.  We look forward to  working with you in these respects.  We
welcome any questions you may have about our comments or any other aspect of our review.  Feel free to call us at the telephone numbers listed at the end of this letter.
 Form 10-K for the Fiscal Year Ended December 31, 2008

 Item 5.  Market for the Registrant’s Common Equity…, page 29

 1. It does not appear that the company included a perf ormance graph in its 2008
annual report to security holders.  Please  provide us with the performance graph
and confirm that the company will provide the performance graph to security holders in accordance with Item 201(e) of Regulation S-K in future filings.

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 2

Item 10. Directors, Executive Officers,  and Corporate Governance, page 32

2. Please revise to describe the business e xperience, including principal occupations
and employment, of Mr. Sloan during the past  five years.  Refer to Item 401(e) of
Regulation S-K.
 Item 11. Executive Compensation, page 32

 General

 3. You state that the sections in th e proxy statement marked “Executive
Compensation”, “Director Compensati on”, “Compensation Discussion and
Analysis” and “Compensation Committee Report” are furnished for the information of the Commission and are not deemed “filed” as part of the Form
10-K.  Other than the information required by Item 407(e)(5) of Regulation S-K, all of the information you reference is f iled, and not furnished.  Please file an
amendment to the Form 10-K confirming that these sections, other than the Compensation Committee Report, are incor porated into the Form 10-K and are
deemed filed, or provide the informati on required by Part III of Form 10-K.
Please also confirm that you will revi se your future filings accordingly.
 Compensation Discussion and Analysis, page 12 of Definitive Proxy Statement

 4. We note that the company benchmarks certain elements of compensation to its
peers.  Please identify, and revise future filings to disclose, the component companies that make up the compensation peer group(s) and the basis for selecting the peer group(s).  Refer to  Item 402(b)(2)(xiv) of Regulation S-K.
 Individual Goals Component, page 18 of Definitive Proxy Statement

 5. Please tell us why you have not disclose d certain of the performance targets
utilized in determining annual bonus compensation for your named executive
officers for the 2008 fiscal year.  For exam ple, you have not disclosed the specific
targets for return on equity, efficiency ra tio, total net charge-offs, net interest
margin and total loan growth that were used as bases for determining the individual component of the annual bonuses  for your named executive officers.
To the extent you believe that disclosure of the historical performance targets is
not required because it would result in competitive harm such that the targets
could be excluded under Instruction 4 to Item 402(b) of Regulation S-K, please
provide a detailed supplemental anal ysis supporting your conclusion.  In
particular, your competitive harm anal ysis should clearly explain the nexus
between disclosure of the performance objectives and the competitive harm that is likely to result from disclosure.  Refer to Item 402(b)(2)(v) of Regulation S-K and Regulation S-K Compliance and Disclosure Interpretation 118.04.

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 3

Item 13. Certain Relationships and Related Transactions…, page 33

 Transactions with Management, page 35 of Definitive Proxy Statement

 6. We note the disclosure on pages 35-36 of your definitive proxy statement that the
loans were made on substantially the same  terms as those prevailing at the time
for comparable transactions with other pers ons.  Please confirm, and revise future
filings to disclose, if true, that the loans were made on substantially the same terms, including interest rates and collate ral, as those prevailing at the time for
comparable loans with persons not related to the lender
.  Refer to Instruction 4(c)
to Item 404(a) of Regulation S-K.
 Signatures, page 36

 7. Please tell us if the report has been  signed by the company’s controller or
principal accounting officer.  Refer to Gene ral Instruction D(2)(a) to Form 10-K.
 Management’s Discussion and Analysis, page 48

 8. We note your disclosure that approxima tely $53.6 million of the problem loan
total was acquired through the Heritage Bank acquisition.  Further, we note you
carried over approximately $3.0 million of a llowance related to the loans acquired
from Heritage Bank.  Please tell us how  you considered whether any of the
acquired loans were within the scope of SOP 03-3 on the acquisition date.  To the
extent that you are accounting for so me of the acquired loans under SOP 03-3,
please revise your future filings to more clearly reflect that fact.
 Notes to Consolidated Financial Statements

 Note D: Securities, page 76

 9. We note the significant unrealized losses  related to your collateralized debt
obligations (backed by trust preferred s ecurities) at December 31, 2008.  We have
the following comments:

• Please provide us a detailed analysis of the securities’ impairment as of December 31, 2008 that identifies all avai lable evidence, explains the relative
significance of each piece of evidence, a nd identifies the primary evidence on
which you rely to support a realizable value equal to or greater than the
carrying value of the investment.  Speci fically tell us if  you considered all
available evidence, including informati on received after ye ar end, affecting
the projected cash flows as of the peri od end.  We may have further comment
based on your response.

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 4

• Please provide us with, and consider disclosing in future filings, a table
detailing the following information for these securities: deal name, single-
issuer or pooled, class, book value, fair  value, unrealized gain/loss, credit
ratings, number of banks in issuance, de ferrals and defaults as a dollar amount
and percentage of collatera l, and excess subordination.

10. We note the significant unrealized losses re lated to your investments in states and
political subdivisions.  Further, we no te your disclosure on page 27 that the
majority of your investments in tax-ex empt state and local municipalities are
insured by monoline insure rs, one of which was downgraded and two others
which were placed on rating review.  Pl ease tell us how you considered these
facts when determining no other than  temporary impairment existed on these
securities as of December 31, 2008.  Add itionally, tell us whether any of the
monoline insurers were downgraded subs equent to year e nd, and explain how
those downgrades (if any) were factored into your year end anal ysis.  Specify the
ratings of those insurers were “secure” or “vulnerable” as of December 31, 2008
and as of March 31, 2009.
 11. Please address the following regarding your  disclosure on page 67 regarding your
investment in stock of the Federal Ho me Loan Bank of Chicago, including your
statement that the stock is redeemable at par:

• Please revise your disclosures in future filings to discuss the regulatory order
issued to the FHLB Chicago that ge nerally requires approval prior to
redeeming or paying dividends on common stock.

• Please refer to paragraph 8(i) of SOP 01-6 and revise your future filings to
disclose your impairment policies for thes e investments.  Clearly disclose how
you determined this investment was not ot her than temporarily impaired as of
the balance sheet date.  Discuss the positive and negative factors you
considered, including the fact that the FHLB Chicago is subject to a
regulatory order that generally requires  approval prior to redeeming or paying
dividends on common stock, the fact th at they have had a significant amount
of losses prior to December 31, 2008, and that they had cumulative losses for the twelve months ended December 31, 2008.

• Provide us with your proposed future disclosure.

Note U: Fair Values of Financial Instruments, page 93

• We note you use a third-part y pricing agent, consensus pricing and dealer
quotes to value certain of your investment securities.  Please tell us and revise

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 5

your future filings to di sclose the following:

• The number of prices you generally obt ain per instrument, and if you obtained
multiple prices, how you determine the ultimate fair value used in your
financial statements;

• Whether, an if so, how and why, you adju sted prices obtained from the pricing
service; and
 • If true, please include an affirmative statement that based on your internal
review procedures, the fair values provided by the pricing services are
consistent with the principals of SFAS 157.

Form 8-K filed April 21, 2009

 Exhibit 99.1

 12. We note your presentation of “tangible capital to tangi ble assets” and “tangible
capital to risk-weighted assets.”   Thes e ratios appear to be  non-GAAP measures
as defined by Regulation G and Item 10(e) of Regulation S- K as they are not
required by GAAP, Commi ssion Rules, or banking regulatory requirements.  To
the extent you plan to provide these non-GAAP  ratios in the future, the staff notes
the following:

• To the extent these ratios are disclosed in future filings with the Commission,
you should comply with all of the requir ements in Item 10(e) of Regulation S-
K, including clearly labe ling the ratios as non-GAAP measures and complying
with all of the disclosure requirements.

• To the extent that you plan to disclose these ratios in future Item 2.02 Form 8-
Ks, you should provide all of the disclosures required by Item 10(e)(1)(i) of
Regulation S-K as required by Instructi on 2 to Item 2.02 of Form 8-K.

• To the extent you disclose or release publicly any material information that
includes a non-GAAP measure, you should be cognizant of the requirements in Regulation G to label the measure as non-GAAP and provide a reconciliation to the most clos ely comparable GAAP measure.

• As it relates to the presentation of risk we ighted assets, in future filings, please
generally disclose how risk weighted a ssets are calculated  under regulatory
capital rules and specifically state, if  true, that the nu mber disclosed is
calculated consistent with banking regulatory requirements.

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 6

Closing Comments

 As appropriate, please amend your filing and respond to these comments within
10 business days or tell us when you will provid e us with a response.  You may wish to
provide us with marked copies of the amendm ent to expedite our review.  Please furnish
a cover letter with your amendment that keys your responses to our comments and provides any requested information.  Detailed co ver letters greatly faci litate our review.
Please understand that we may have addi tional comments after reviewing your
amendment and responses to our comments.    We urge all persons who are responsi ble for the accuracy an d adequacy of the
disclosure in the filing to be certain that the filing includes all in formation required under
the Securities Exchange Act of 1934 and th at they have provided all information
investors require for an informed invest ment decision.  Since the company and its
management are in possession of all facts re lating to a company’s disclosure, they are
responsible for the accuracy and adequacy of the disclosures they have made.
  In connection with responding to our comments, please provide, in writing, a statement from the company acknowledging that:
• the company is responsible for the adequacy  and accuracy of the disclosure in the
filing;

• staff comments or changes to disclosure  in response to staff comments do not
foreclose the Commission from taking any action with respect to the filing; and
 • the company may not assert staff comme nts as a defense in any proceeding
initiated by the Commission or any person under the federal secu rities laws of the
United States.

In addition, please be advise d that the Division of Enfo rcement has access to all
information you provide to the staff of the Divi sion of Corporation Fi nance in our review
of your filing or in response to our comments on your filing.

J. Douglas Cheatham
Old Second Bancorp, Inc. April 27, 2009 Page 7

 You may contact Sharon Blume, Assist ant Chief Accountant, at (202) 551-3474
or Kevin Vaughn, Accounting Branch Chief, at (202) 551-3494 if you have questions
regarding comments on the fina ncial statements and relate d matters.  Please contact
Justin Dobbie at (202) 551-3469 or me at  (202) 551-3419 with any other questions

Sincerely,

Christian Windsor Special Counsel