Castlewood Holdings LTD Sample Contracts

ARTICLE III REPRESENTATIONS AND WARRANTIES
Merger Agreement • June 1st, 2006 • Castlewood Holdings LTD • Investors, nec • New York
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ENSTAR GROUP LIMITED 3.100% Senior Notes due 2031 UNDERWRITING AGREEMENT
Underwriting Agreement • August 24th, 2021 • Enstar Group LTD • Fire, marine & casualty insurance • New York

Conditions to Redemption and Repayment; Replacement Capital Covenant: Notwithstanding anything to the contrary set forth herein, (i) prior to March 31, 2025, the Notes may be redeemed only with BMA Approval, and (ii) the Notes may not be redeemed at any time or repaid prior to the Final Maturity Date if the Enhanced Capital Requirement would be breached immediately before or after giving effect to the redemption or repayment of such Notes, unless, in the case of each of clauses (i) and (ii), the Issuer or a subsidiary of the Issuer replaces the capital represented by the Notes to be redeemed or repaid with capital having equal or better capital treatment as the Notes under the Group Rules, provided that if under Applicable Supervisory Regulations no such consent is required at the time in order for the Notes to qualify, or continue to qualify, as applicable, as Tier 3 Capital of the Issuer or the Insurance Group, clause (i) shall not apply (collectively, the “BMA Redemption Requirement

BACKGROUND
Employment Agreement • September 20th, 2006 • Castlewood Holdings LTD • Fire, marine & casualty insurance • Delaware
WITNESETH:
License Agreement • July 11th, 2006 • Castlewood Holdings LTD • New York
EXHIBIT 99.2 SUPPORT AGREEMENT DATED AS OF MAY 23, 2006
Support Agreement • June 1st, 2006 • Castlewood Holdings LTD • Investors, nec • New York
ENSTAR GROUP LIMITED (a Bermuda exempted company) [l] Ordinary Shares (Par Value $1.00 Per Share) PURCHASE AGREEMENT
Purchase Agreement • June 26th, 2008 • Enstar Group LTD • Fire, marine & casualty insurance • New York

FOX-PITT KELTON COCHRAN CARONIA WALLER (USA) LLC DOWLING & PARTNERS SECURITIES, LLC as Representatives of the several Underwriters c/o Fox-Pitt Kelton Cochran Caronia Waller (USA) LLC One South Wacker Drive Chicago, Illinois 60606

RECITAL
Indemnification Agreement • January 31st, 2007 • Castlewood Holdings LTD • Fire, marine & casualty insurance
BACKGROUND
Employment Agreement • January 31st, 2007 • Castlewood Holdings LTD • Fire, marine & casualty insurance • Delaware
ENSTAR GROUP LIMITED AND THE BANK OF NEW YORK MELLON, as TRUSTEE SENIOR INDENTURE Dated as of March 10, 2017
Senior Indenture • March 10th, 2017 • Enstar Group LTD • Fire, marine & casualty insurance • New York

Provisions of Trust Indenture Act of 1939 and Indenture dated as of March 10, 2017, between Enstar Group Limited and The Bank of New York Mellon, as Trustee:

RECITAL
Indemnification Agreement • July 11th, 2006 • Castlewood Holdings LTD
AGREEMENT AND PLAN OF MERGER among ENSTAR GROUP LIMITED AML ACQUISITION, CORP. and SEABRIGHT HOLDINGS, INC. dated as of August 27, 2012
Merger Agreement • August 28th, 2012 • Enstar Group LTD • Fire, marine & casualty insurance • Delaware

AGREEMENT AND PLAN OF MERGER, dated as of August 27, 2012 (this “Agreement”), among Enstar Group Limited, a Bermuda exempted company (“Parent”), AML Acquisition, Corp., a Delaware corporation and an indirect, wholly-owned subsidiary of Parent (“Merger Sub”), and SeaBright Holdings, Inc., a Delaware corporation (the “Company”).

EMPLOYMENT AGREEMENT
Employment Agreement • August 7th, 2015 • Enstar Group LTD • Fire, marine & casualty insurance

This EMPLOYMENT AGREEMENT (“Agreement”) is dated as of May 11, 2015, between Enstar Group Limited, a Bermuda corporation (“Company”), and Mark Smith (“Executive”).

ENSTAR FINANCE LLC, as Issuer ENSTAR GROUP LIMITED, as Guarantor AND The Bank of New York Mellon, as TRUSTEE JUNIOR SUBORDINATED INDENTURE Dated as of August 26, 2020
Junior Subordinated Indenture • August 26th, 2020 • Enstar Group LTD • Fire, marine & casualty insurance • New York

Section of the Act Section of Indenture 310(a)(1) and (2) 6.8 310(a)(3) and (4) Inapplicable 310(b) 6.9 311(a) 6.12 311(b) 6.12 312(a) 4.1 and 4.2 312(b) 4.2 312(c) 4.2 313(a) 4.3 313(b) 4.3 313(c) 4.3, 5.11, 6.9, 6.10, 8.2 and 14.2 313(d) 4.3 314(a) 3.4 and 3.9 314(b) Inapplicable 314(c)(1) and (2) 13.5 314(c)(3) Inapplicable 314(d) Inapplicable 314(e) 13.5 314(f) Inapplicable 315(a), (c) and (d) 6.1 315(b) 5.11 315(e) 5.12 316(a)(1) 5.9 316(a)(2) Inapplicable 316(a) (last sentence) 7.4 316(b) 5.7 316(c) 7.2 317(a) 5.2 317(b) 3.3 318(a) 13.7 (*) This Cross-Reference Sheet is not part of the Indenture.

PERFORMANCE STOCK UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATED ENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN
Performance Stock Unit Award Agreement • May 7th, 2021 • Enstar Group LTD • Fire, marine & casualty insurance

This Performance Stock Unit Award Agreement (this “Agreement”) is entered into as of the Grant Date (as defined below), by and between the Grantee (as defined below) and Enstar Group Limited (the “Company”). Except as otherwise defined herein, capitalized terms used in this Agreement have the respective meanings set forth in the Plan (as defined below).

AMENDED AND RESTATED EMPLOYMENT AGREEMENT
Employment Agreement • January 27th, 2020 • Enstar Group LTD • Fire, marine & casualty insurance

This EMPLOYMENT AGREEMENT (“Agreement”) is dated as of January 21, 2020 between Enstar Group Limited, a Bermuda corporation (“Company”), and Paul O’Shea (“Executive”) and amends and restates in its entirety all previous Employment Agreements between Company and Executive.

DEPOSIT AGREEMENT November 21, 2018
Deposit Agreement • November 21st, 2018 • Enstar Group LTD • Fire, marine & casualty insurance • New York

DEPOSIT AGREEMENT, dated November 21, 2018 among ENSTAR GROUP LIMITED, a Bermuda exempted company (the “Company”), AMERICAN STOCK TRANSFER & TRUST COMPANY, LLC, a New York limited liability trust company, as Depositary (as hereinafter defined), as Registrar (as hereinafter defined), as Transfer Agent (as hereinafter defined), and as Dividend Disbursing Agent (as hereinafter defined) and Redemption Agent (as hereinafter defined), and all holders from time to time of Receipts (as hereinafter defined) issued hereunder.

AMENDED AND RESTATED EMPLOYMENT AGREEMENT
Employment Agreement • May 2nd, 2024 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This Amended and Restated Employment Agreement (“Agreement”) is made by and between Enstar (US) Inc., a Delaware corporation (the “Company”), and Nazar Alobaidat (“Executive”). The Company is a subsidiary of Enstar Group Limited (collectively, with its subsidiaries, “Enstar”).

ENSTAR GROUP LIMITED (a Bermuda exempted company) [l] Ordinary Shares (Par Value $1.00 Per Share) PURCHASE AGREEMENT
Purchase Agreement • June 25th, 2008 • Enstar Group LTD • Fire, marine & casualty insurance • New York

Enstar Group Limited, a Bermuda exempted company (the “Company”), and the persons listed in Schedule II hereto (the “Selling Shareholders”), hereby confirm their respective agreements with Fox-Pitt Kelton Cochran Caronia Waller (USA) LLC (“FPK”), Dowling & Partners Securities, LLC (“Dowling”) and each of the other Underwriters named in Schedule I hereto (collectively, the “Underwriters,” which term shall also include any underwriter substituted as hereinafter provided in Section 10 hereof), for whom FPK and Dowling are acting as representatives (in such capacity, the “Representatives”), with respect to (i) the sale by the Company and the Selling Shareholders, acting severally and not jointly, and the purchase by the Underwriters, acting severally and not jointly, of the respective numbers of ordinary shares, par value $1.00 per share, of the Company (“Ordinary Shares”) set forth in Schedules I and II hereto and (ii) the grant by the Company and certain of the Selling Shareholders ident

REGISTRATION RIGHTS AGREEMENT
Registration Rights Agreement • April 4th, 2014 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This REGISTRATION RIGHTS AGREEMENT, dated as of April 1, 2014 (this “Agreement”), is made among ENSTAR GROUP LIMITED, a Bermuda company (the “Company”), and FR XI Offshore AIV, L.P., First Reserve Fund XII, L.P., FR XII A Parallel Vehicle L.P. and FR Torus Co-Investment, L.P. (collectively, the “First Reserve Shareholder”) and Corsair Specialty Investors, L.P. (the “Corsair Shareholder”, and together with the First Reserve Shareholder, the “Shareholders” or individually a “Shareholder”).

MASTER AGREEMENT
Master Agreement • May 8th, 2019 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This MASTER AGREEMENT, dated as of March 1, 2019 (this “Agreement”), is made by and among Maiden Holdings, Ltd., a Bermuda company (“Maiden”), Maiden Reinsurance Ltd., a Bermuda insurance company (“Maiden Insurance”), and Enstar Group Limited, a Bermuda company (“Enstar”). Capitalized terms used but not otherwise defined herein have the respective meanings set forth in Section 1.1.

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AMENDED AND RESTATED SHAREHOLDERS’ AGREEMENT between NORTHSHORE HOLDINGS LIMITED and THE SHAREHOLDERS NAMED HEREIN dated as of 5 March, 2015
Shareholders Agreement • May 11th, 2015 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This Amended and Restated Shareholders’ Agreement (this “Agreement”), dated as of March 5, 2015, is entered into among Northshore Holdings Limited, a Bermuda exempted company (the “Company”), Kenmare Holdings Ltd (the “Enstar Shareholder”), Trident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P. (each, a “Trident Shareholder” and, collectively, the “Trident Shareholders” and, together with the Enstar Shareholder, the “Initial Shareholders”), Dowling Capital Partners I, L.P. (the “Dowling Shareholder”), Atrium Nominees Limited (the “Atrium Nominee”), each other Person who after the date hereof acquires Common Shares of the Company and becomes a party to this Agreement by executing a Joinder Agreement (such Persons, collectively with the Initial Shareholders, the Dowling Shareholder and the Atrium Nominee, the “Shareholders”) and, solely for purposes of Section 3.05 hereof, Enstar Group Limited (“Enstar”).

AMENDED AND RESTATED AGREEMENT AND PLAN OF AMALGAMATION BY AND AMONG ENSTAR GROUP LIMITED, VERANDA HOLDINGS LTD., HUDSON SECURITYHOLDERS REPRESENTATIVE LLC (solely in its capacity as the Securityholders’ Representative), AND TORUS INSURANCE HOLDINGS...
Agreement and Plan of Amalgamation • April 29th, 2014 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This AMENDED AND RESTATED AGREEMENT AND PLAN OF AMALGAMATION (this “Agreement”), dated as of March 11, 2014, is made by and among Enstar Group Limited, a Bermuda exempted company (“Parent”), Veranda Holdings Ltd., a Bermuda exempted company and an indirect subsidiary of Parent (“Amalgamation Sub”), Torus Insurance Holdings Limited, a Bermuda exempted company (the “Company”), and Hudson Securityholders Representative LLC, a Delaware limited liability company, solely in its capacity as the Securityholders’ Representative (the “Securityholders’ Representative”). Parent, Amalgamation Sub and the Company and, solely in its capacity as the Securityholders’ Representative and solely to the extent applicable, the Securityholders’ Representative, shall be referred to herein from time to time collectively as the “Parties”. Capitalized terms used but not otherwise defined herein have the meanings set forth in Section 1.1.

PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, ELK EVERGREEN INVESTMENTS, LLC and ELK CYPRESS INVESTMENTS, LLC November 8, 2023 PURCHASE AGREEMENT
Purchase Agreement • September 4th, 2024 • Enstar Group LTD • Fire, marine & casualty insurance • Delaware

This Purchase Agreement (this “Agreement”) is dated as of November 8, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), Elk Evergreen Investments, LLC, a Delaware limited liability company (“Evergreen Purchaser”), and Elk Cypress Investments, LLC (“Cypress Purchaser” and together with Evergreen Purchaser, the “Purchasers”).

Contract
Joint Ownership Agreement • July 6th, 2022 • Enstar Group LTD • Fire, marine & casualty insurance • England and Wales
AMENDED AND RESTATED REVOLVING CREDIT AGREEMENT dated as of May 30, 2023 between ENSTAR GROUP LIMITED, as Parent ENSTAR GROUP LIMITED KENMARE HOLDINGS LTD. ENSTAR (US ASIA-PAC) HOLDINGS LIMITED ENSTAR HOLDINGS (US) LLC and CAVELLO BAY REINSURANCE...
Revolving Credit Agreement • June 1st, 2023 • Enstar Group LTD • Fire, marine & casualty insurance • New York

Page ARTICLE I DEFINITIONS SECTION 1.01 Defined Terms 1 SECTION 1.02 Terms Generally 32 SECTION 1.03 Accounting Terms; Changes in GAAP 33 SECTION 1.04 Rates 33 SECTION 1.05 Exchange Rates; Currency Equivalents 33 SECTION 1.06 Change of Currency 33 SECTION 1.07 Letter of Credit Amounts 34 SECTION 1.08 Divisions 34 ARTICLE II COMMITMENTS AND CREDIT EXTENSIONS SECTION 2.01 Commitments 34 SECTION 2.02 Loans and Borrowings 35 SECTION 2.03 Borrowing Requests 35 SECTION 2.04 Swingline Loans 36 SECTION 2.05 Reserved 37 SECTION 2.06 Funding of Borrowings 37 SECTION 2.07 Interest Elections 37 SECTION 2.08 Prepayments 38 SECTION 2.09 Termination or Reduction of Commitments 39 SECTION 2.10 Repayment of Loans 39 SECTION 2.11 Interest 40 SECTION 2.12 Fees 40 SECTION 2.13 Evidence of Debt 41 SECTION 2.14 Payments Generally; Several Obligations of Lenders 41 SECTION 2.15 Sharing of Payments 42 SECTION 2.16 Compensation for Losses 43 SECTION 2.17 Increased Costs 43 SECTION 2.18 Taxes 44 SECTION 2.19

PURCHASE AGREEMENT
Purchase Agreement • November 13th, 2023 • Enstar Group LTD • Fire, marine & casualty insurance

This Purchase Agreement (this “Agreement”) is dated as of November 7, 2023, by and between Trident Public Equity LP, a Delaware limited partnership (“Trident”), and Enstar Group Limited, a Bermuda exempted company (“Enstar”).

RESTRICTED STOCK UNIT AWARD AGREEMENT UNDER THE AMENDED AND RESTATEDENSTAR GROUP LIMITED 2016 EQUITY INCENTIVE PLAN
Restricted Stock Unit Award Agreement • February 27th, 2020 • Enstar Group LTD • Fire, marine & casualty insurance

This Restricted Stock Unit Award Agreement (this “Agreement”) is entered into as of the Grant Date (as defined below), by and between the Grantee (as defined below) and Enstar Group Limited (the “Company”). Except as otherwise defined herein, capitalized terms used in this Agreement have the respective meanings set forth in the Plan (as defined below).

PURCHASE AGREEMENT
Purchase Agreement • March 28th, 2023 • Enstar Group LTD • Fire, marine & casualty insurance

This Purchase Agreement (this “Agreement”) is dated as of March 23, 2023 by and between Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), and Enstar Group Limited, a Bermuda exempted company (“Enstar”).

AMENDED AND RESTATED EMPLOYMENT AGREEMENT
Employment Agreement • January 27th, 2020 • Enstar Group LTD • Fire, marine & casualty insurance

This EMPLOYMENT AGREEMENT (“Agreement”) is dated as of January 21, 2020, between Enstar Group Limited, a Bermuda corporation (“Company”), and Orla M. Gregory (“Executive”) and amends and restates in its entirety all previous Employment Agreements between Company and Executive.

INVESTORS AGREEMENT
Investors Agreement • August 9th, 2013 • Enstar Group LTD • Fire, marine & casualty insurance • New York

This Shareholders’ Agreement (this “Agreement”), dated as of [•], 2013, is entered into among Bayshore Holdings Limited, a Bermuda exempted company (the “Company”), Kenmare Holdings Ltd (the “Enstar Shareholder”), Trident V, L.P., Trident V Parallel Fund, L.P. and Trident V Professionals Fund, L.P. (each, a “Trident Shareholder” and, collectively, the “Trident Shareholders” and, together with the Enstar Shareholder, the “Initial Shareholders”), each other Person who after the date hereof acquires Common Shares of the Company and becomes a party to this Agreement by executing a Joinder Agreement (such Persons, collectively with the Initial Shareholders, the “Shareholders”) and, solely for purposes of Section 3.05 hereof, Enstar Group Limited (“Enstar”).

May 23, 2006 To the undersigned parties
Recapitalization Agreement • June 1st, 2006 • Castlewood Holdings LTD • Investors, nec

Reference is made to the transactions contemplated by (i) the Agreement and Plan of Merger (the “Merger Agreement”), dated as of May 23, 2006, among Castlewood Holdings Limited, a Bermuda company (“Castlewood”), The Enstar Group, Inc., a Georgia corporation (“Enstar”) and CWMS Subsidiary Corp., a Georgia corporation and (ii) the Recapitalization Agreement (the “Recapitalization Agreement”), dated as of May 23, 2006, among Castlewood, Enstar and the other parties named on the signature pages thereto. Capitalized terms used herein without definition have the meanings given to them in the Merger Agreement or if not so defined in the Merger Agreement, the Recapitalization Agreement.

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