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Alan Bossin is a partner in the Corporate department in Bermuda. Alan specialises in insurance and reinsurance with a focus on mergers and acquisitions, corporate finance, and private equity and regulatory matters. His significant experience includes representing public and private acquirors and target companies in a variety of Bermuda corporate acquisitions.

Alan also has extensive experience in capital raising, securitisation, insurance-linked, longevity and distinctive risk transference transactions utilising special purpose vehicles, catastrophe (CAT) bond structures, capital markets and segregated accounts. He regularly advises on the establishment of all classes of insurance companies and the regulatory regime governing Bermuda insurers.

Work Highlights

  • S&P GLOBAL, Advised S&P Global in its USD 140 billion merger with IHS Markit;
  • HORSESHOE INSURANCE SERVICES HOLDINGS LTD., Acted as counsel to the sellers of Horseshoe Insurance Services Holdings Ltd. in connection with the sale of the Horseshoe group to Artex Risk Solutions (Holdings) Limited, a subsidiary of Arthur J. Gallagher & Co;
  • ASPEN INSURANCE HOLDINGS LIMITED, Acted for Aspen Insurance Holdings Limited during a competitive sale process (valued at c. $2.6 billion) which was won by private equity firm Apollo Global Management LLC;
  • VALIDUS HOLDINGS LTD., Advised Validus on its $5.6 billion acquisition by American International Group, Inc.  Appleby demonstrated the strength and depth of its corporate team on this transaction with a combination of specialist M&A and regulatory lawyers forming the deal team;
  • 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;
  • SOMPO CANOPIUS AG, Assisted in the structuring and formation of a new insurance linked securities platform for the Canopius Group providing qualified investors with access to the underwriting expertise of Canopius;
  • BARBICAN INSURANCE GROUP, Acted as regulatory counsel to Barbican Insurance Company, a multi-jurisdictional insurance/reinsurance holding company, in establishing a Bermuda platform for accessing a significant existing portfolio to facilitate underwriting on behalf of a major Lloyds syndicate;
  • GLOBAL BANKERS INSURANCE GROUP, LLC, Acted as lead counsel to Global Banker Insurance Group, LLC in connection with their acquisition of certain entities within the Beechwood Group which was a family of reinsurance and asset management companies;
  • HERITAGE REINSURANCE COMPANY, Assisted in an important group restructuring of a major international insurance company including the merger of two dual-licenced insurers, Heritage Reinsurance Company and Fencourt Reinsurance Company;
  • PARTNERRE LTD., Acted for PartnerRe Ltd. in its agreement and plan of merger with EXOR S.p.A under which EXOR will acquire all of the outstanding shares of PartnerRe. The total transaction is valued at USD 6.9 billion;
  • CANADA PENSION PLAN INVESTMENT BOARD ASCOT UNDERWRITING HOLDINGS LTD., 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;
  • 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 13billion;
  • HORSESHOE GROUP, Advised as lead counsel on the acquisition of IKONIC Fund Services, allowing Horseshoe Group to solidify its stance as the largest independent insurance manager for the ILS market;
  • SOMPO CANOPIUS AG, Acted in connection with the sale of the excess casualty book of business to Bermuda’s Hamilton Re;
  • AEOLUS CAPITAL MANAGEMENT LTD. (ACM), Advised on the sale of a controlling interest in the company to Elliott Management Corporation. The transaction significantly broadened the reach and impact of ACM and has created an enduring and growing franchise with a materially heightened recognition level;
  • GENSTAR CAPITAL, Acted as Bermuda counsel to Genstar Capital (Genstar) in its entry into definitive agreements to recapitalize independent fund administrator Apex Fund Services (“Apex”) and simultaneously acquire Equinoxe Alternative Investment Services (“Equinoxe”). With the addition of Equinoxe, Apex will increase its suite of middle office solutions and will administer close to $80 billion in assets;
  • FOSUN INTERNATIONAL LIMITED, Advised in the acquisition of the remaining 80% equity interest in Ironshire Inc. by way of merger;
  • Advised on the creation of a brand new private catastrophe bond, including the incorporation, organisation and registration of the exempted company as an SPI and SAC;
  • IRIS REINSURANCE LTD., Advised on the creation of its new collateralised reinsurance platform, including the creation of insurance-linked preferred shares and listing on the Bermuda Stock Exchange;
  • CHINA MINSHENG INVESTMENT CO. LTD., Advised in the acquisition of the entire issued share of capital of Sirius International Insurance Group, Ltd. The transaction was one of the largest private acquisitions in the Bermuda reinsurance space;
  • Advised a (re)insurance company on a joint venture with a private equity firm in the formation of a new Bermuda company that will be the holding company for funds offering insurance-linked and traditional insurance products. Appleby’s role included incorporating the company and advising on elements of the joint venture, such as the constitutional documents and shareholders agreement;
  • ONTARIO TEACHERS’ PENSION PLAN, Advised in the acquisition of SeaCube Container Leasing Ltd. (“SeaCube”), the world’s largest container leasing companies based on total assets. Under the terms of the agreement and plan of amalgamation, SeaCube shareholders received USD 23.00 per share in cash, for a total equity value of USD 469.5 million and an enterprise value (including assumed debt) of USD 1.8 billion;
  • EVERGLADES RE LTD., USD 1.5 billion issuance through Bermuda special purpose insurer Everglades Re Ltd., provides collateralized reinsurance covering hurricane losses in the state of Florida for the benefit of Citizens Property Insurance. The transaction was the largest catastrophe bond ever issued; breaking new ground for the ILS market and ILS investors;
  • AMERICAN SAFETY INTERNATIONAL HOLDINGS, LTD., Advised in the acquisition by Fairfax Financial Holdings Limited, a Canadian firm, of the shares of American Safety International Holdings, Ltd (ASI), a Bermuda domiciled specialist insurer and reinsurer with operations in Bermuda and the U.S;
  • VECTOR REINSURANCE LTD., Acted as Bermuda legal counsel to the XL Group in the establishment of Vector Reinsurance Ltd., which is licensed as a special purpose insurer to participate in collateralised reinsurance and other non-traditional risk placements for the XL Group;
  • NEW OCEAN CAPITAL MANAGEMENT LIMITED, Launched investment platform incorporating strategies dedicated to the insurance and reinsurance capital markets by New Ocean Capital Management Limited;
  • KITTY HAWK INSURANCE COMPANY LIMITED, Advised on substantial and complex issues involved in arbitration in which +$1 billion claimed against Kitty Hawk’s insured (Air Line Pilots Association (ALPA)) settled at mediation in New York;
  • MANULIFE (INTERNATIONAL) LIMITED, Successfully completed a scheme under Section 25 of the Insurance Act to transfer Manulife (International) Limited’s Taiwan life insurance business to CTBC Life Insurance Co Ltd, a Taiwan life insurance company;
  • Advised on first tranche of catastrophe bond principal-at-risk notes accepted for listing on the BSX under a newly established ILS Note Program.


Alan is consistently ranked by Chambers Global since 2009, where he is described as “client-friendly and a great partner to have on innovative and fast-paced transactions.” Clients recommend Alan as “dynamic and a great problem solver,” while others are keen to emphasis the impressive technical detail of his advice. Alan is consistently recommended by Legal 500 Caribbean in the Insurance/Reinsurance category and IFLR1000 in the Corporate and Commercial and Insurance/Reinsurance categories. He has also been ranked by Who’s Who Legal as ‘Internationally Recognised’ for Insurance and Reinsurance.

Coverage & Insights

His expertise is sought for participation at conferences and seminars, and providing commentary to international and Bermuda media on the Bermuda and global insurance industry, including:


Qualifications & Education

  • University of Guelph (Canada)
  • University of Windsor (Canada)


Chambers & Partners

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