Exhibit 10.14 QUOTA SHARE TREATY OF WELLINGTON UNDERWRITING INC PROPERTY BUSINESS REINSURED: Wellington Reinsurance Limited, London, United Kingdom. PERIOD: Continuous contract always open in respect of risks attaching on or after the 1st January...Aspen Insurance Holdings LTD • November 25th, 2003 • Fire, marine & casualty insurance • London
Company FiledNovember 25th, 2003 Industry Jurisdiction
EXHIBIT 10.2 FORM OF THIRD AMENDED AND RESTATED REGISTRATION RIGHTS AGREEMENT This Third Amended and Restated Registration Rights Agreement, dated as of November 14, 2003 (this "Agreement"), among Aspen Insurance Holdings Limited (formerly known as...Registration Rights Agreement • November 25th, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledNovember 25th, 2003 Company Industry Jurisdiction
W I T N E S S E T H : - - - - - - - - - - WHEREAS, the parties hereto desire to amend the Credit Agreement on the terms and subject to the conditions set forth herein. NOW, THEREFORE, in consideration of the premises herein contained and for other...Credit Agreement • August 9th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledAugust 9th, 2004 Company Industry Jurisdiction
ANDService Agreement • September 24th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledSeptember 24th, 2004 Company Industry
Exhibit 4.11 SHAREHOLDER'S AGREEMENT ----------------------- This Shareholder's Agreement (this "Agreement") is entered into as of [o], 2003, between Aspen Insurance Holdings Limited, a Bermuda corporation (the "Company"), and the undersigned person...Shareholder's Agreement • February 4th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 4th, 2005 Company Industry
EXHIBIT 1.1 ASPEN INSURANCE HOLDINGS LIMITED ORDINARY SHARES, PAR VALUE 0.15144558(CENTS) PER SHARE UNDERWRITING AGREEMENTUnderwriting Agreement • December 3rd, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledDecember 3rd, 2003 Company Industry Jurisdiction
W I T N E S S E T H : - - - - - - - - - -Credit Agreement • August 9th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledAugust 9th, 2004 Company Industry Jurisdiction
EXHIBIT 4.4 FIRST SUPPLEMENTAL INDENTUREFirst Supplemental Indenture • October 14th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledOctober 14th, 2004 Company Industry Jurisdiction
TOAspen Insurance Holdings LTD • February 4th, 2005 • Fire, marine & casualty insurance • New York
Company FiledFebruary 4th, 2005 Industry Jurisdiction
amongGuarantee and Collateral Agreement • November 25th, 2003 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledNovember 25th, 2003 Company Industry Jurisdiction
EXHIBIT 4.5 ASPEN INSURANCE HOLDINGS LIMITED 6.00% SENIOR NOTES DUE 2014 EXCHANGE AND REGISTRATION RIGHTS AGREEMENTExchange and Registration Rights Agreement • October 14th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledOctober 14th, 2004 Company Industry Jurisdiction
ANDService Agreement • March 14th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledMarch 14th, 2005 Company Industry
PERIOD: Continuous contract always open in respect of ------- risks attaching on or after the 1st January 2003, subject to six months prior notice of cancellation to be tendered by the Reinsurer and three months prior notice of cancellation to be...Aspen Insurance Holdings LTD • November 25th, 2003 • Fire, marine & casualty insurance • London
Company FiledNovember 25th, 2003 Industry Jurisdiction
EXHIBIT 10.23 ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENT THIS AGREEMENT (the "Agreement"), is made effective as of the 22nd day of December, 2004, between Aspen Insurance Holdings Limited, a Bermuda corporation (hereinafter...Performance Share Award Agreement • March 14th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledMarch 14th, 2005 Company Industry
W I T N E S S E T H : - - - - - - - - - - WHEREAS, the parties hereto desire to amend the Credit Agreement on the terms and subject to the conditions set forth herein. NOW, THEREFORE, in consideration of the premises herein contained and for other...Credit Agreement • August 9th, 2004 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledAugust 9th, 2004 Company Industry Jurisdiction
AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018Agreement and Plan of Merger • August 28th, 2018 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Delaware
Contract Type FiledAugust 28th, 2018 Company Industry JurisdictionThis AGREEMENT AND PLAN OF MERGER (this “Agreement”) dated as of August 27, 2018, among Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”), Highlands Holdings, Ltd., a Bermuda exempted company (“Parent”), and Highlands Merger Sub, Ltd., a Bermuda exempted company and a wholly owned Subsidiary of Parent (“Merger Sub”).
AGREEMENT AND PLAN OF MERGER by and among HIGHLANDS HOLDINGS, LTD. HIGHLANDS MERGER SUB, LTD. and ASPEN INSURANCE HOLDINGS LIMITED Dated as of August 27, 2018Agreement and Plan of Merger • December 20th, 2023 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Delaware
Contract Type FiledDecember 20th, 2023 Company Industry JurisdictionThis AGREEMENT AND PLAN OF MERGER (this “Agreement”) dated as of August 27, 2018, among Aspen Insurance Holdings Limited, a Bermuda exempted company (the “Company”), Highlands Holdings, Ltd., a Bermuda exempted company (“Parent”), and Highlands Merger Sub, Ltd., a Bermuda exempted company and a wholly owned Subsidiary of Parent (“Merger Sub”).
SERVICE AGREEMENTService Agreement • February 22nd, 2017 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 22nd, 2017 Company Industry
UNDERWRITING AGREEMENTUnderwriting Agreement • August 7th, 2019 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledAugust 7th, 2019 Company Industry Jurisdiction
ASPEN INSURANCE HOLDINGS LIMITED Ordinary Shares UNDERWRITING AGREEMENTUnderwriting Agreement • May 14th, 2008 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledMay 14th, 2008 Company Industry Jurisdiction
ASPEN INSURANCE HOLDINGS LIMITED LTIP RESTRICTED SHARE UNIT AWARD AGREEMENTLtip Restricted Share Unit Award Agreement • February 22nd, 2018 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 22nd, 2018 Company IndustryTHIS RESTRICTED SHARE UNIT AWARD AGREEMENT (the “Agreement”), is made effective as of 10th February 2017, between Aspen Insurance Holdings Limited, a Bermuda corporation (hereinafter called the “Company”), and [NAME] (hereinafter called the “Participant”).
CHANGE OF CONTROL EMPLOYMENT AGREEMENTChange of Control Employment Agreement • February 19th, 2016 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • England
Contract Type FiledFebruary 19th, 2016 Company Industry JurisdictionTHIS CHANGE OF CONTROL EMPLOYMENT AGREEMENT (this “Agreement”) by and among Aspen Insurance Holdings Limited, a Bermuda corporation (“Holdings”), Aspen Insurance UK Services Limited, an England corporation (the “Company”) and Stephen Postlewhite (the “Executive”) is dated as of the 23rd day of February 2015.
PLEDGE AGREEMENTPledge Agreement • October 13th, 2006 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledOctober 13th, 2006 Company Industry JurisdictionPLEDGE AGREEMENT, dated as of 17 JANUARY 2006, (this ‘‘Agreement’’) made among Aspen Insurance Ltd, a company organized and existing under the laws of Bermuda (the ‘‘Pledgor’’), and Citibank, N.A. (the ‘‘Pledgee’’).
EMPLOYMENT AGREEMENTEmployment Agreement • February 19th, 2016 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Connecticut
Contract Type FiledFebruary 19th, 2016 Company Industry JurisdictionAGREEMENT (the “Agreement”), dated and entered into as of January 24, 2011, between Aspen Insurance U.S. Services Inc., a Delaware corporation, (the “Company”), and Emil Issavi (the “Executive”).
ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENTRestricted Share Unit Award Agreement • February 13th, 2019 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 13th, 2019 Company Industry
EXHIBIT 10.22 ASPEN INSURANCE HOLDINGS LIMITED NONQUALIFIED SHARE OPTION AGREEMENT THIS AGREEMENT (the "Agreement"), is made effective as of the 22nd day of December, 2004 (hereinafter called the "Date of Grant"), between Aspen Insurance Holdings...Nonqualified Share Option Agreement • March 14th, 2005 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledMarch 14th, 2005 Company Industry
CHANGE OF CONTROL EMPLOYMENT AGREEMENTChange of Control Employment Agreement • February 19th, 2016 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • Connecticut
Contract Type FiledFebruary 19th, 2016 Company Industry JurisdictionTHIS CHANGE OF CONTROL EMPLOYMENT AGREEMENT (this “Agreement”) by and among Aspen Insurance Holdings Limited, a Bermuda corporation (“Holdings”), Aspen Insurance U.S. Services Inc., a Delaware corporation (the “Company”) and Emil Issavi (the “Executive”) is dated as of the 24th day of February 2015.
THE BANK OF NEW YORK MELLON,Credit Agreement • May 4th, 2017 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledMay 4th, 2017 Company Industry JurisdictionSECOND AMENDED AND RESTATED CREDIT AGREEMENT (this “Agreement”), dated as of March 27, 2017, among ASPEN INSURANCE HOLDINGS LIMITED, a Bermuda exempted limited liability company (the “Company”), the Subsidiary Borrowers (as defined below; together with the Company, collectively, the “Borrowers” and individually, a “Borrower”), the several banks and other financial institutions or entities from time to time parties to this Agreement (the “Lenders”), CITIBANK, N.A., as syndication agent (in such capacity, the “Syndication Agent”), DEUTSCHE BANK SECURITIES INC., THE BANK OF NEW YORK MELLON and LLOYDS SECURITIES INC., as co-documentation agents (in such capacities, each a “Co-Documentation Agent”), THE BANK OF NEW YORK MELLON, as collateral agent, and BARCLAYS BANK PLC, as administrative agent.
ASPEN INSURANCE HOLDINGS LIMITED PERFORMANCE SHARE AWARD AGREEMENTPerformance Share Award Agreement • February 28th, 2012 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 28th, 2012 Company IndustryTHIS AGREEMENT (the “Agreement”), is made effective as of the 9th day of February, 2011 (hereinafter called the “Date of Grant”), between Aspen Insurance Holdings Limited, a Bermuda corporation (hereinafter called the “Company”), and «Full_Name» (hereinafter called the “Participant”):
ASPEN INSURANCE HOLDINGS LIMITED RESTRICTED SHARE UNIT AWARD AGREEMENTRestricted Share Unit Award Agreement • February 26th, 2013 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledFebruary 26th, 2013 Company IndustryTHIS AWARD AGREEMENT (the “Agreement”), is made effective as of the 1st day of November 2012, between Aspen Insurance Holdings Limited, a Bermuda corporation (hereinafter called the “Company”), and John Worth (hereinafter called the “Participant”):
CERTAIN IDENTIFIED INFORMATION HAS BEEN EXCLUDED FROM THIS EXHIBIT BECAUSE IT IS BOTH NOT MATERIAL AND IS THE TYPE THAT THE REGISTRANT TREATS AS PRIVATE OR CONFIDENTIAL AMENDED AND RESTATED REINSURANCE AGREEMENT by and among ASPEN INSURANCE UK...Reinsurance Agreement • December 20th, 2023 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance • New York
Contract Type FiledDecember 20th, 2023 Company Industry JurisdictionThis AMENDED AND RESTATED REINSURANCE AGREEMENT, dated as of January 10, 2022 (this “Agreement”), is made by and among Aspen Insurance UK Limited, a company incorporated in England and Wales, Aspen Managing Agency Limited, a company incorporated in England and Wales, for and on behalf of the underwriting members(s) of Lloyd’s Syndicate 4711, Aspen Bermuda Limited, a company incorporated in Bermuda, Aspen American Insurance Company, a Texas-domiciled insurance company, Aspen Specialty Insurance Company, a North Dakota-domiciled insurance company (individually or collectively, “Aspen”), Aspen Insurance Holdings Limited, a company incorporated in Bermuda (“Aspen Parent”) (solely for the purposes of Sections 11.1, 13.2, 14.1, 16.3, 16.9, 16.12, 16.13 and 16.16) and Cavello Bay Reinsurance Limited, a Bermuda insurance company (the “Reinsurer”). Capitalized terms used but not otherwise defined herein have the respective meanings set forth in Section 1.1.
JULIAN MICHAEL CUSACK AND ASPEN INSURANCE UK SERVICES LIMITED AMENDED AND RESTATED SERVICE AGREEMENTService Agreement • November 7th, 2011 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledNovember 7th, 2011 Company Industry
ASPEN INSURANCE HOLDINGS LIMITED NON-EMPLOYEE DIRECTOR RESTRICTED SHARE UNIT AWARD AGREEMENTRestricted Share Unit Award Agreement • May 9th, 2007 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledMay 9th, 2007 Company IndustryTHIS AWARD AGREEMENT (the ‘‘Agreement’’), is made effective as of the day of 20 (hereinafter called the ‘‘Date of Grant’’), between Aspen Insurance Holdings Limited, a Bermuda corporation (hereinafter called the ‘‘Company’’), and (hereinafter called the ‘‘Participant’’):
Insurance Letters of Credit − Master AgreementAspen Insurance Holdings LTD • December 20th, 2023 • Fire, marine & casualty insurance
Company FiledDecember 20th, 2023 IndustryTo: Citibank Ireland Financial Services plcInsurance Letter of Credit Department2nd Floor1 North Wall QuayDublin 1Republic of Ireland
ContractSettlement Agreement • July 5th, 2018 • Aspen Insurance Holdings LTD • Fire, marine & casualty insurance
Contract Type FiledJuly 5th, 2018 Company IndustryTHIS EXHIBIT HAS BEEN REDACTED AND IS THE SUBJECT OF A CONFIDENTIAL TREATMENT REQUEST. REDACTED MATERIAL IS MARKED WITH [***] AND HAS BEEN FILED SEPARATELY WITH THE SECURITIES AND EXCHANGE COMMISSION.