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Gary Harris is a partner in the Corporate department at Appleby Bermuda, where he provides strategic legal counsel to clients on complex corporate transactions, with a focus on the insurance and banking sectors. His experience includes advising on large (US$1bn+) mergers and acquisitions, financings, and risk transfer deals.

Prior to rejoining Appleby in October 2022, Gary served for three years as Head of Legal and Compliance in Bermuda for a leading global composite reinsurer. Earlier in his career, he spent six years at Appleby Bermuda honing his expertise in corporate and insurance law.

With over a decade of experience spanning both private practice and in-house roles, Gary offers valuable insights into the legal and compliance considerations of insurance, reinsurance, and banking institutions. He leverages his deep experience advising on high-value, complex transactions to provide practical and strategic legal advice to clients undertaking major deals and navigating regulatory matters.

CLIENT Recognition

“Gary Harris is an exceptional partner. He is extremely responsive and thoughtful. His pragmatic, useful advice never wastes my time. He is one of the best I have ever worked with – I could not recommend him more highly.” – Legal 500 

“Gary Harris and Brad Adderley are terrific partners. Tireless effort and great substantive experience both in Bermuda and more broadly.” – Legal 500 

Work Highlights


  • Digicel, Advised in relation to the $4.4 Billion in the aggregate Digicel restructuring;
  • Brookfield Reinsurance Ltd., Appleby Bermuda advised Brookfield Reinsurance in connection with its $1.1 Billion Acquisition of Argo Group;
  • Sumitomo Dainippon Pharma – advised Sumitomo Dainippon Pharma, a leading Japanese pharmaceutical company in respect of its estimated USD 3 billion acquisition of 5 biopharma companies
  • T&D Holdings – advised T&D Holdings on USD 1.8 Billion joint acquisition with Carlyle Group of Fortitude Re
  • IHS Inc. – advised in relation to the Bermuda elements of the proposed merger with Markit Ltd, a leading global provider of financial information services, valued at USD 13 billion
  • Crown Global Titan Life Insurance Ltd. (“Crown Global”) – advised on the sale of 81% of its shares by Crown Global Holdings Ltd. by way of a share transfer agreement
  • Canada Pension Plan Investment Board Ascot Underwriting Holdings Ltd. – advised Ascot Underwriting Bermuda Ltd and Ascot Corporate Name Ltd., as a capital provider for Syndicate 1414 at Lloyds, with a matter value of USD 1.1 billion
  • KeyTech Limited. – advised in connection with a multi-layered transaction including the acquisition of the remainder of Bermuda Digital Communications Ltd. (CellOne) and the acquisition by Atlantic Tele-Network, Inc., of a controlling interest in Keytech


  • Blackstone – Appleby Bermuda advised in the $3bn equity capital raise of Resolution Life and Blackstone
  • Prismic Life Reinsurance Ltd. – advised Prudential Financial, Inc. and Warburg Pincus LLC, in the launch of Prismic Life Reinsurance, Ltd., a licensed Class E Bermuda-based life and annuity reinsurance company
  • Kuvare Side Car – advised Kuvare Holdings (Kuvare) on its formation of Kindley Re Ltd. (Kindley Re), a newly formed Bermuda-domiciled reinsurer which will co-invest at least USD 400 million with Kuvare in qualifying life insurance and annuity transactions
  • HSBC – represented HSBC in a GBP 7 billion longevity swap and reinsurance transaction which is the second largest on record. This new HSBC deal is the first that sees a bank offloading the longevity risk associated with its pension plan members, which could suggest a broadening of appeal for these deals
  • 777 Re Ltd. – assisted with the formation and licensing of 777 Re. Ltd. as a Class D insurer and acted as legal counsel in relation to the company’s first transaction
  • Hannover Life Reassurance Company of America (Bermuda) Ltd. – assisted a major global life reinsurer in responding to changing US regulations in the upgrading and relicensing of a Bermuda Class C insurer into a major Class E insurer able to engage in a new global platform with a substantive mandate
  • Allianz Re Bermuda Life Ltd.- advised in relation to the incorporation and licensing of Allianz Re Bermuda Life Ltd, a Bermuda Class E insurer
  • Kuvare Holdings LP. – advised in relation to the formation and structuring of Kuvare Life Re Ltd., a Bermuda exempted company registered as a class E insurer


  • African Risk Capacity Ltd – advised ARC Ltd, a long-standing client, on its first parametric insurance product against high-impact epidemic risks
  • Convex Group Limited – acted as Bermuda counsel to Convex Group, a newly launched specialty re/insurer. The group has been capitalised initially with approximately USD 1.6 billion of common shareholders’ equity, drawn from a USD 1.8 billion facility provided by a consortium of investors. Convex Group Limited is a specialty insurer and reinsurer focused on complex risks founded by Stephen Catlin and Paul Brand, with operations in Bermuda and London
  • PGGM – advised PGGM (the pension fund manager) in their partnership with RenaissanceRe on a new risk-remote rated property catastrophe reinsurance vehicle named Vermeer Reinsurance Ltd. Matter value USD 1 billion
  • Athene Holding Ltd – advised on Athene Holding Ltd. (Athene)’s secondary offering of $793.8 million of shares. Appleby provided advice on submitting the SEC S-1 and opined and commented on the transaction documents
  • Veritas Group Limited. – advised on Veritas Group Limited (Veritas)´s Bermuda Stock Exchange listings of 10,000,000 class A common shares with a view to promote Veritas’ business of issuing financial insurance guarantee to investors
  • White Rock Insurance (SAC) Ltd. – advised White Rock Insurance (SAC) Ltd., a Class 3 insurer, on the listing on the Bermuda Stock Exchange of the White Rock Insurance (SAC) Ltd ILS Program. Appleby’s role included assisting in setting up the program, corresponding with the Bermuda Stock Exchange, and reviewing transaction documentation such as the base prospectus and the note purchasing agreement
  • Sunpoint Reinsurance Ltd. -advised on the incorporation of the client to serve as a run-off platform for Fosun Insurance Group


  • Investec Bank Plc – provided legal advice in connection with Investec Bank plc providing a master facility to Oakley Capital Private Equity
  • Atherton Bermuda Hold Co Ltd. (“Atherton”) – advised Atherton Bermuda Hold Co Ltd. (“Atherton”) on a USD 400,000,000 letter of credit facility between Atherton (in its capacity as the Account Party); ING Bank N.V., London Branch, Lloyds Bank plc, The Bank of Nova Scotia, London Branch (together as original banks, lead arrangers and bookrunners) and ING Bank N.V., London Branch separately as issuing bank, agent, and security agent
  • Major UK listed bank – advised a major UK listed bank (in its capacity as arranger, original lender, agent and security agent) on a USD150,000,000 amendment and restatement agreement made between the bank and a major Bermuda based insurance group
  • Ocean Bank- advised in relation to an investment contract between Butterfield (Bermuda) Limited and Sunlife Financial Investments


  • Matterhorn Re Ltd. – acted as Bermuda counsel to Matterhorn Re Ltd. in connection with the sale and issue by the company, acting in respect of its segregated account, of Class A Principal At-Risk Variable Rate Notes
  • Alturas Re Ltd. – advised AXIS Capital, the Bermuda-headquartered global re/insurer, in the creation and funding of its sidecar Alturas Re Ltd. The total note issuance size was $130 million
  • Tullett Prebob – advised Tullett Prebon, one of the world´s leading interdealer brokers, on the launch of their Insurance-Linked Notes (ILN) platform which will allow registered users to buy or sell natural catastrophe protection using customisable instruments
  • Tailwind Re Ltd. – advised Bermuda- headquartered reinsurance firm Validus Holdings on its first full catastrophe bond issuance with the Tailwind Re Ltd., valued at $400 million
  • Spectrum Capital Ltd. – advised on its first full cat bond issuance from Tokio Millennium Re (Bermuda) during its upsize from original $250 million to $430 million, thanks to investor appetite and pricing
  • Hoplon III – advised on the incorporation and organisation of a special purpose insurer, Hoplon III, and the formation of the purpose trust pursuant to the third insurance-linked (ILS) securities transaction from MyLotto24, a UK-based lottery provider owned by the Zeal Group. Matter value €90 million


Gary is recommended in the Insurance/Reinsurance category in Legal 500. One source explained: “Gary Harris is an exceptional partner. He is extremely responsive and thoughtful. His pragmatic, useful advice never wastes my time. He is one of the best I have ever worked with – I could not recommend him more highly.”  Another source commented: “Gary Harris and Brad Adderley are terrific. Tireless effort and great substantive experience both in Bermuda and more broadly.”

He was also recognised in Bermuda:Re+ILS as a ´Rising Star´, which features highly regarded professionals in Bermuda under the age of 35.

Coverage & Insights

Qualifications & Education

Gary holds an LLB (Hons) degree from the University of Liverpool and obtained two Master’s degrees from the University of Cambridge and UCL in International Business Law.

  • University College London (England)
  • University of Cambridge (England)
  • University of Liverpool (England)

Memberships & Associations

Gary is a member of the Honourable Society of the Inner Temple and the Bermuda Bar Association, and is a non-practicing member of both the Bar Council for England and Wales and the Jamaican Bar Association.

Related People

Brad Adderley

Managing Partner: Bermuda

T +1 441 298 3243
E Email Brad

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Matthew Carr

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Josephine Noddings

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Matthew Ebbs-Brewer

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Sally Penrose

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Jerome Wilson

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Ryann Hollis

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Kinika Armstrong

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Larissa Dziubenko

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Jane Walker

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Ojeda Smith

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