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FORM 4UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940
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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).
1. Name and Address of Reporting Person*
ALLEGHANY CORP /DE

(Last)(First)(Middle)
7 TIMES SQUARE TOWER 17TH FLOOR

(Street)
NEW YORKNY10036

(City)(State)(Zip)
2. Issuer Name and Ticker or Trading Symbol
Darwin Professional Underwriters Inc [DR]
5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)
XDirectorX10% Owner
Officer (give title below)Other (specify below)
3. Date of Earliest Transaction (Month/Day/Year)
10/20/2008
4. If Amendment, Date of Original Filed (Month/Day/Year)
6. Individual or Joint/Group Filing (Check Applicable Line)
Form filed by One Reporting Person
XForm filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1.Title of Security
(Instr. 3)
2. Transaction Date (Month/Day/Year)2A. Deemed Execution Date, if any (Month/Day/Year)3. Transaction Code
(Instr. 8)
4. Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4 and 5)
5. Amount of Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 3 and 4)
6. Ownership Form: Direct (D) or Indirect (I)
(Instr. 4)
7. Nature of Indirect Beneficial Ownership
(Instr. 4)
CodeVAmount(A) or (D)Price
Common Stock 10/20/2008 J(1)  9,371,096 D$ 32 0 I See Footnote (2)

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security
(Instr. 3)
2. Conversion or Exercise Price of Derivative Security3. Transaction Date (Month/Day/Year)3A. Deemed Execution Date, if any (Month/Day/Year)4. Transaction Code
(Instr. 8)
5. Number of Derivative Securities Acquired (A) or Disposed of (D)
(Instr. 3, 4, and 5)
6. Date Exercisable and Expiration Date
(Month/Day/Year)
7. Title and Amount of Underlying Securities
(Instr. 3 and 4)
8. Price of Derivative Security
(Instr. 5)
9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s)
(Instr. 4)
10. Ownership Form of Derivative Security: Direct (D) or Indirect (I)
(Instr. 4)
11. Nature of Indirect Beneficial Ownership
(Instr. 4)
CodeV(A)(D)Date ExercisableExpiration DateTitleAmount or Number of Shares
1. Name and Address of Reporting Person*
ALLEGHANY CORP /DE

(Last)(First)(Middle)
7 TIMES SQUARE TOWER 17TH FLOOR

(Street)
NEW YORKNY10036

(City)(State)(Zip)
1. Name and Address of Reporting Person*
ALLEGHANY INSURANCE HOLDINGS LLC

(Last)(First)(Middle)
7 TIMES SQUARE TOWER 17TH FLOOR

(Street)
NEW YORKNY10036

(City)(State)(Zip)
Explanation of Responses:
1. Disposed of pursuant to merger agreement by and among the issuer, Allied World Assurance Company Holdings, Ltd and Allied World Merger Company in exchange for a cash payment of $32.00 per share on the effective date of the merger.
2. Owned directly by Alleghany Insurance Holdings LLC ("AIHL") and beneficially owned indirectly by Alleghany Corporation ("Alleghany"), which is the sole stockholder of AIHL. This report is filed jointly by Alleghany and AIHL, 7 Times Square Tower, New York, New York 10036. Because, until the effective time of the merger, AIHL owned, and Alleghany beneficially owned, more than 50% of the issued and outstanding shares of DR common stock and AIHL had elected two Alleghany officers to serve as its representatives on the Board of Directors of DR, each of AIHL and Alleghany may be deemed to have been, until the effective time of the merger, a director by deputization of DR.
Aileen C. Meehan (attorney-in-fact for Alleghany Corporation)10/21/2008
Aileen C. Meehan (attorney-in-fact for Alleghany Insurance Holdings LLC)10/21/2008
** Signature of Reporting PersonDate
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4(b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

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