Sec Form 4 Filing - ProSight Global Holdings Ltd @ TIPTREE FINANCIAL INC. - 2016-06-27

FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED 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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1. Name and Address of Reporting Person ProSight Global Holdings Ltd 2. Issuer Name and Ticker or Trading Symbol TIPTREE FINANCIAL INC. [ TIPT] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director X __ 10% Owner _____ Officer (give title below) _____ Other (specify below) (Last) (First) (Middle) 1 CLARENDON HOUSE, 2 CHURCH STREET 3. Date of Earliest Transaction (MM/DD/YY) 06/27/2016 (Street) HAMILTON, D0HM11 4. If Amendment, Date Original Filed (MM/DD/YY) 6. Individual or Joint/Group Filing (Check Applicable Line) _____ Form filed by One Reporting Person __ X __ Form filed by More than One Reporting Person (City) (State) (Zip)

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned 1.Title of Security (Instr. 3) 2. Transaction Date (MM/DD/YY) 2A. Deemed Execution Date, if any (MM/DD/YY) 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) Code V Amount (A) or (D) Price Class A Common Stock 06/23/2016 S 3,242,882 D $ 6.5 0 I By New York Marine & General Insurance Company ( 1 ) ( 2 ) Class A Common Stock 06/23/2016 S 1,411,591 D $ 6.5 0 I By Gotham Insurance Company ( 1 ) ( 2 ) Class A Common Stock 06/23/2016 S 941,527 D $ 6.5 0 I By Southwest Marine and General Insurance Company ( 1 ) ( 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 Security 3. Transaction Date (MM/DD/YY) 3A. Deemed Execution Date, if any (MM/DD/YY) 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 (MM/DD/YY) 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) Code V (A) (D) Date Exercisable Expiration Date Title Amount or Number of Shares

Reporting Owners Reporting Owner Name / Address Relationships Director 10% Owner Officer Other ProSight Global Holdings Ltd 1 CLARENDON HOUSE 2 CHURCH STREET HAMILTON, D0HM11 X ProSight Global, Inc. 412 MT. KEMBLE AVENUE SUITE 300C MORRISTOWN, NJ07960 X ProSight Specialty Insurance Group, Inc. 412 MT. KEMBLE AVENUE SUITE 300C MORRISTOWN, NJ07960 X NEW YORK MARINE & GENERAL INSURANCE Co 412 MT. KEMBLE AVENUE SUITE 300C MORRISTOWN, NJ07960 X Southwest Marine & General Insurance Co 412 MT. KEMBLE AVENUE SUITE 300C MORRISTOWN, NJ07960 X Gotham Insurance Co 412 MT. KEMBLE AVENUE SUITE 300C MORRISTOWN, NJ07960 X Signatures /s/ Eric Bernstein, Director, ProSight Global Holdings Limited 06/27/2016 Signature of Reporting Person Date /s/ Anthony Piszel, Chief Financial Officer, ProSight Global, Inc. 06/27/2016 Signature of Reporting Person Date /s/ John Fitzgerald, Controller, ProSight Specialty Insurance Group, Inc. 06/27/2016 Signature of Reporting Person Date /s/ John Fitzgerald, Controller, New York Marine and General Insurance Company 06/27/2016 Signature of Reporting Person Date /s/ John Fitzgerald, Controller, Southwest Marine and General Insurance Company 06/27/2016 Signature of Reporting Person Date /s/ John Fitzgerald, Controller, Gotham Insurance Company 06/27/2016 Signature of Reporting Person Date

Explanation of Responses:

( 1 )This statement is being filed jointly on behalf of ProSight Global Holdings Limited ("PGHC"), ProSight Global, Inc. ("PGI"), ProSight Specialty Insurance Group, Inc. ("PSIG"), New York Marine and General Insurance Company ("NY Marine"), Southwest Marine and General Insurance Company ("SW Marine"), and Gotham Insurance Company ("Gotham," together with PGHC, PGI, PSIG, NY Marine, and SW Marine, the "Reporting Persons"). SW Marine and Gotham are wholly owned subsidiaries of NY Marine. NY Marine is a wholly owned subsidiary of PSIG. PSIG is a wholly owned subsidiary of PGI. PGI is a wholly owned subsidiary of PGHC. Each Reporting Person disclaims beneficial ownership of the securities reported herein except to the extent of its pecuniary interest, if any. ( 2 )The 5,596,000 shares of class A common stock, par value $0.001 per share ("Common Stock") of TipTree Financial Inc. (the "Company") whose dispostion is being reported in this Form 4 were previously directly owned by NY Marine, SW Marine and Gotham (each a "Seller" and collectively, the "Sellers"). Pursuant to that certain Stock Purchase Agreement, dated as of June 23, 2016 (the "Purchase Agreement"), by and among the Company, Caroline Holdings LLC, a Delaware limited liability company (the "Buyer"), the Sellers, and PSIG, the Sellers sold to the Buyer and the Buyer purchased from the Sellers, 5,596,000 shares of Common Stock for an aggregate purchase price of $36,374,000. As a result of the foregoing, as of June 23, 2016, the reporting persons ceased to be the beneficial owners of more than 10% of the Common Stock and are therefore no longer subject to Section 16 of the Securities Exchange Act of 1934, as amended.

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