SecProbe.io

June 25, 2014

Via E -mail
Michael Groll, Esq.
Willkie, Farr & Gallagher LLP
787 Seventh Avenue
New York, NY  10019

Re: Aspen Insurance Holdings Limited
 Schedule 14D-9
Filed June 17, 2014
File No. 005 -79396

Dear Mr. Groll :

We have limited our review of your filing to the issues addressed in 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 filing, by providing the requested
information, or by advising us when you will provide the requested response.   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 filing and the information you provide in
response to these  comments, we may have  additional comments.

General

1. Please tell us whether Aspen provided its employees with access to  a video , the contents
of which related to Endurance’s proposal to acquire Aspen.  If so, please tell us why this
video, including a transcription, was not filed under applicable rules, such as Rule 425 of
Regulation C and Exchange Act Rule 14a -12.  Please also provide us a copy of these
materials.

Background of the Offer, page 16

2. We note the disclosure regarding the June 2, 2014 press release .  We also note  that in
such press release, Aspen states  that its shareholders do not support Endurance’s
acquisition proposal.  Given that it appears from Aspen’s disclosure that the proposal has
not yet been presented to shareholders, please tell us the basis for this statement.   Also
revise applicable futur e filings to clarify the basis of any statements  regarding the
opinions of Aspen shareholders relating to  the offer by Endurance .

Michael Groll , Esq.
Aspen Insurance Holdings Limited
June 25, 2014
Page 2

3. Please refer to the disclo sure on page 24 regarding the press release Aspen issued  on June
9, 2014 .  While the disclosure indicates the  content of that  communication was limited to
the matters specified in Rules 14d -9(b) and (f), the information actually included appears
to be beyond what is authorized by those rules.  Please revise your disclosure and future
filings accordingly.

Reasons for the Recommendation of the Aspen Board o f Directors, page 25

4. We note the “factors” the Board considered , as referenced here and page 35 .  Please
revise to clarify the reasons  for making their recommendation.  See Item 1012(b) of
Regulation M -A.

The Offer significantly undervalues Aspen, page  25

5. We note the use of the comparative term “undervalues.”  While we also note the multiple
bullet points included under this heading, it is unclear how the matters disclosed support
the conclusion that Endurance’s offer undervalues Aspen, inasmuch as the disclosure
does not indicate a value for Aspen  derived by the Board.  Therefore, p lease revise to
clarify  how the “Offer” undervalues Aspen .

6. As a related matter, we  note the financial advisor’s opinion related to the inadequacy of
the offer and that Asp en’s disclosure does not include a summary of its analysis or any
projections  Aspen  provided to it.  Notwithstanding the absence of an item requiring such
disclosure, please tell us, with a view toward disclosure, what consideration has been
given to discl osing the analyses and projections underlying the financial advisor’ s
opinion so that Aspen shareholders are better able to assess the basis for Aspen’s and the
financial advisor’s conclusions regarding the adequacy of the offered consideration.

The Offer is replet e with uncertainties and onerous conditions, page 34

7. Please clarify how the failed “Say -on-Pay” noted in the disclosure relates to the
likelihood of Endurance’s ability to win approval for the transaction from its own
shareholders.  The connection Aspen i s seeking to make is unclear, particularly given that
Endurance’s other proposals  at the referenced  meeting, including the election of
directors,  were approved by substantial majorities.

Cautionary Statement . . ., page 49

8. Please revise to delete reference here and in exhibits (a)(1) -(3) to inapplicable safe
harbors.  See Exchange Act Section 21E(b)(2)(C).

We urge all persons who are responsible for the accuracy and adequacy of the disclosure
in the filing to be certain that the fili ng includes the information the Securities Exchange Act of

Michael Groll , Esq.
Aspen Insurance Holdings Limited
June 25, 2014
Page 3

 1934 and all applicable Exchange 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.

 In responding to our comments, please provide  a written 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 comments as a defense in any proceeding initiated by
the Commission or any person under the federal securities laws of the United States.

Please contact Nicholas Panos , Senior Special Counsel, at (202) 551-3266  or me at (202)
551-3641 with any questions.

Sincerely,

 /s/ Geoff Kruczek

Geoff Kruczek
        Attorney -Adviser
        Office  of Mergers & Acquisitions