0001047469-06-007892 Sample Contracts

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Agreement is made pursuant to the Purchase/Placement Agreement (the “Purchase/Placement Agreement”), dated as of March 27, 2006, by and between the Company and FBR in connection with the purchase and sale or placement of an aggregate of 23,500,000 shares of the Company’s common shares (plus an additional 3,525,000 shares to cover additional allotments, if any). In order to induce FBR to enter into the Purchase/Placement Agreement, the Company has agreed to provide the registration rights provided for in this Agreement to FBR, the Participants, and their respective direct and indirect transferees. The execution of this Agreement is a condition to the closing of the transactions contemplated by the Purchase/Placement Agreement.

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EMPLOYMENT AGREEMENT
Employment Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

THIS AGREEMENT (the “Agreement”), dated as of April 4, 2006, is by and between CastlePoint Holdings, Ltd., a Bermuda exempted company (the “Company”), and Michael H. Lee (the “Executive”).

MASTER AGREEMENT
Master Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Agreement (“Agreement”) is made this 4th day of April, 2006 by and between Tower Group, Inc, a Delaware corporation (“TGI”), Tower Insurance Company of New York (“TICNY), a New York Corporation, and Tower National Insurance Company (“TNIC”) a Massachusetts corporation, (collectively “Tower”) and CastlePoint Holdings, Ltd. (“CPH”), a Bermuda exempted corporation, and CastlePoint Management Corp., (“CPM”), a Delaware corporation (collectively “CastlePoint”).

CASTLEPOINT HOLDINGS, LTD. 23,500,000 Shares of Common Stock PURCHASE/PLACEMENT AGREEMENT
Purchase/Placement Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

CastlePoint Holdings, Ltd., a Bermuda company limited by shares (the “Company”), proposes to issue and sell to you, Friedman, Billings, Ramsey & Co., Inc. (“FBR”), as initial purchaser, a number of common shares, par value $0.01 per share, of the Company (the “Common Stock”) equal to 23,500,000 shares less the number of Regulation D Shares sold in the Private Placement (each as defined herein) (the “144A/Regulation S Shares”).

AMENDMENT NO. 1 TO SPECIALTY PROGRAM BUSINESS AND INSURANCE RISK SHARING BUSINESS QUOTA SHARE REINSURANCE AGREEMENT
Share Reinsurance Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This AMENDMENT No. 1 (this “Amendment”), dated as of May 26, 2006 (the “Effective Date”), to the Specialty Program Business and Insurance Risk Sharing Business Quota Share Reinsurance Agreement (the “Agreement”) by and among Tower Insurance Company of New York, Tower National Insurance Company and CastlePoint Reinsurance Company, Ltd., effective April 5, 2006. Capitalized terms used but not defined herein shall have the meanings ascribed thereto in the Agreement.

SERVICE AND EXPENSE SHARING AGREEMENT
Service and Expense Sharing Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd.

This (“Agreement”) is entered into as of April 10, 2006 (April 28, 2006 with respect to Tower National Insurance Company) by and between Tower Insurance Company of New York (“TICNY”) and Tower National Insurance Company (“TNIC”) , property and casualty insurance companies domiciled in New York and Massachusetts, respectively, (both insurance companies collectively referred to as Tower insurance companies or “TIC”) and Tower Risk Management Corp. (“TRM”), an insurance services company domiciled in New York (TIC and TRM are collectively referred to as “Tower”) with offices located at 120 Broadway, New York, N.Y. 10271 and CastlePoint Management Corp. and any of its after acquired property and casualty insurance company subsidiaries (collectively “CPM”), a Delaware corporation with offices located at 120 Broadway, New York, N.Y. 10271.

FORM OF TRADITIONAL PROGRAM BUSINESS POOLING AGREEMENT
Form of Traditional Program Business Pooling Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Traditional Program Business Pooling Agreement (“Pooling Agreement”) by and between Tower Insurance Company of New York (“TICNY”), an insurance company domiciled in New York, Tower National Insurance Company (“TNIC”), an insurance company domiciled in Massachusetts (collectively called “Tower”) and CastlePoint Insurance Company (“CPIC”), an insurance company domiciled in [ ], is dated this day of , 200[ ], and is made effective as of 12:01 a.m., [ ], 200[ ], (the “Effective Date”).

FORM OF SPECIALTY PROGRAM BUSINESS POOLING AGREEMENT
Pooling Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Specialty Program Business Pooling Agreement (“Pooling Agreement”) by and between Tower Insurance Company of New York (“TICNY”), an insurance company domiciled in New York, Tower National Insurance Company (“TNIC”), an insurance company domiciled in Massachusetts, (collectively called “Tower”), and CastlePoint Insurance Company (“CPIC”), an insurance company domiciled in [ ], is dated this day of , 200[ ], and is made effective as of 12:01 a.m., [ ], 200[ ], (the “Effective Date”).

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”) is made and entered into as of April 4, 2006 by and between TOWER GROUP, INC., a Delaware corporation (the “Investor”), and CASTLEPOINT HOLDINGS, LTD., a Bermuda company (the “Company”).

AMENDMENT NO. 1 TO BROKERAGE BUSINESS QUOTA SHARE REINSURANCE AGREEMENT
Quota Share Reinsurance Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This AMENDMENT No. 1 (this “Amendment”), dated as of May 26, 2006 (the “Effective Date”), to the Brokerage Business Quota Share Reinsurance Agreement (the “Agreement”) by and among Tower Insurance Company of New York, Tower National Insurance Company and CastlePoint Reinsurance Company, Ltd., effective April 5, 2006. Capitalized terms used but not defined herein shall have the meanings ascribed thereto in the Agreement.

Form of Option Agreement For Executive Employees] CastlePoint Holdings, Ltd. 2006 Long Term Equity Compensation Plan Stock Option Agreement
Stock Option Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York
FORM OF BROKERAGE BUSINESS POOLING AGREEMENT
Form of Brokerage Business Pooling Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Brokerage Business Pooling Agreement (“Pooling Agreement”) by and between Tower Insurance Company of New York (“TICNY”), an insurance company domiciled in New York, Tower National Insurance Company (“TNIC”), an insurance company domiciled in Massachusetts (collectively called “Tower”) and CastlePoint Insurance Company (“CPIC”), an insurance company domiciled in [ ], is dated this day of , 200[ ], and is made effective as of 12:01 a.m., [ ], 200[ ], (the “Effective Date”).

PROGRAM MANAGEMENT AGREEMENT
Program Management Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This Agreement, entered into as of April 10, 2006 (April 28, 2006 with respect to Tower National Insurance Company) (the “Agreement”) by and between TOWER INSURANCE COMPANY OF NEW YORK, a property and casualty insurance company domiciled in New York and TOWER NATIONAL INSURANCE COMPANY, a property and casualty insurance company domiciled in Massachusetts (collectively the “Company”), CASTLEPOINT MANAGEMENT CORP., a Delaware corporation (“Manager”), each having offices located at 120 Broadway, New York, N.Y. 10271.

AMENDMENT NO. 1 TO TRADITIONAL PROGRAM BUSINESS QUOTA SHARE REINSURANCE AGREEMENT
Quota Share Reinsurance Agreement • June 1st, 2006 • CastlePoint Holdings, Ltd. • New York

This AMENDMENT No. 1 (this “Amendment”), dated as of May 26, 2006 (the “Effective Date”), to the Traditional Program Business Quota Share Reinsurance Agreement (the “Agreement”) by and among Tower Insurance Company of New York, Tower National Insurance Company and CastlePoint Reinsurance Company, Ltd., effective April 5, 2006. Capitalized terms used but not defined herein shall have the meanings ascribed thereto in the Agreement.

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