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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-