Michael D. Devins

MICHAEL DEVINS primarily focuses his practice on corporate transactions in the insurance industry, including the acquisition, divestiture, and merger of insurance and reinsurance businesses, as well as reinsurance and renewal rights transactions, redomestications and company formations. In addition to transactional matters, Michael represents insurance and reinsurance companies in connection with regulatory matters. He has significant experience representing private equity and other non-traditional purchasers and sellers of insurance companies and insurance-related assets.

Michael has been recognized by several industry publications, including Chambers USA in New York (2025) as a leading lawyer for Insurance: Transactional & Regulatory. IFLR1000 (2020–2024) where he is listed as a “Notable Practitioner” and Legal 500 United States. (2012) which notes that Michael “has an encyclopedia-like understanding of the insurance M&A landscape and the legal framework for getting deals done.”

Prior to joining Sidley, Michael was counsel at another global law firm in its M&A and Insurance Industry groups. Prior to law school, Michael served as a policy advisor to the premier of the Canadian province of Manitoba. He is a frequent writer and speaker on insurance industry and M&A topics.

Michael serves on the Board of Directors and as finance and operations chair of the Jazz Foundation of America and is a member of the Pro Bono and Public Interest Law Committee at Sidley.

Selected examples of Michael’s experience include representation of:

• Medica, a Minnesota-based nonprofit health plan with more than 1.4 million members across nine states, in its definitive agreement to acquire key contracts and assets of UCare.
• Brookfield Wealth Solutions Ltd., a leading provider of retirement services, wealth protection products and tailored capital solutions, in its reinsurance agreement with leading Japanese insurance company Dai-ichi Frontier Life.
• Apollo Global Management on insurance regulatory matters in its acquisition of Bridge Investment Group in an all-stock transaction with an equity value of approximately US$1.5 billion (pending).
• New Enterprise Associates (NEA) on insurance regulatory matters in the take-private acquisition by an NEA affiliate of NeueHealth at an enterprise value of approximately US$1.3 billion (pending).
• The Fortegra Group, Inc., a U.S.-based specialty insurer, in connection with its US$1.65 billion sale to DB Insurance Co., Ltd.
• RGA in the acquisition of a US$4.1 billion block of long-term care and structured settlement business from John Hancock.
• Nassau Financial Group, a Golden Gate Capital portfolio company, in a strategic partnership with Golub Capital, including a US$200 million equity investment by Golub Capital in Nassau and a long-term investment management agreement.
• Nassau Financial Group in obtaining a US$150 million revolving credit facility and a US$100 million term loan credit facility.
• Nassau Financial Group in a strategic partnership with Fortress Investment Group, including a US$130 million equity investment by Fortress in Nassau and a long-term investment management agreement.
• Zinnia in its strategic acquisition of Policygenius, a digital insurance marketplace.
• Nassau Financial Group in its strategic business combination with Angel Island Capital Management.
• Nassau Financial Group in the acquisition of Delaware Life Insurance Company of New York.
• Security Benefit and its subsidiary Everly Holdings in the acquisition of Settlers Life from National Guardian Life.
• The Nassau Companies of New York in cash tender offers for up to a combined US$100 million of outstanding debt securities issued by it and one of its wholly-owned subsidiaries.
• Tiptree and Fortegra on the insurance and regulatory aspects of a US$200 million strategic investment in Fortegra from Warburg Pincus.
• Ambac Financial Group as a lead investor in a US$15.5 million seed funding of Cover Whale Insurance Solutions, an insurtech MGA focused on the commercial auto space.
• Nassau Financial Group in the sale of its life insurance and annuity distribution company, Saybrus Partners, to AmeriLife Group.
• Ambac Financial Group in its acquisition of Xchange Benefits and Xchange Affinity Underwriting Agency, property and casualty managing general underwriters.
• UPC in the transfer of personal lines business in four states to HCI.
• Cornell Capital and Hudson Structured Capital Management in their acquisition of a majority interest in Vault Insurance.
• Kelso & Company, as part of a consortium with Arch Capital Group and Warburg Pincus, in the US$700 million acquisition of Watford Holdings, a global property and casualty insurance and reinsurance company.
• Cornell Capital and its portfolio company Spectrum Automotive Holdings in several acquisitions of vehicle service contract providers.
• Syncora Holdings in its US$429 million sale of Syncora Guarantee, a wholly owned subsidiary, to Star Insurance Holdings, an entity organized by GoldenTree Asset Management LP.
• Tiptree in the acquisition of Smart AutoCare, a vehicle warranty solutions provider.
• Atlas Merchant Capital in its investment in Ascensus, the largest independent recordkeeping services provider, third-party administrator, and government savings facilitator in the United States.
• Risk Strategies, a Kelso & Company portfolio company, in its acquisition of Oxford Risk Management, an established leader in alternative risk and captive insurance and consulting.
• Syncora Holdings in a reinsurance agreement with Assured Guaranty to reinsure approximately US$13.5 billion of financial guaranty policies, representing 91% of Syncora's outstanding insured exposures.
• Cornell Capital as a lead investor in the US$2.05 billion acquisition of Talcott Resolution, The Hartford’s run-off life and annuity businesses.
• American Coastal Insurance Company and its parent, RDX Holding Corp., in its merger with United Insurance Holdings Corp.
• Nassau Reinsurance Group in its acquisition of Universal American’s Traditional Insurance business.
• HC2 Holdings in insurance regulatory aspects of its acquisition of Karawha Insurance Company from Humana.
• Sun Life Financial in two reinsurance agreements, and a related administrative agreement, with affiliates of Enstar Group Limited.
• Nassau Reinsurance Group in its US$217.2 million acquisition of The Phoenix Companies.
• Sun Life Financial in its US$975 million acquisition of Assurant’s Employee Benefits business.
• AmRisc management in its purchase of American Coastal Insurance Company from BB&T, and its sale of a majority interest in AmRisc, a managing general agency, to BB&T.
• HC2 Holdings in its acquisition of American Financial Group’s long-term care businesses.
• Harbinger Group and its subsidiary Front Street Re, in the acquisition of Ability Re by way of a merger of Ability Re with and into Front Street Re, with Front Street Re as the surviving entity.
• Tiptree Financial in the insurance aspects of its agreement to acquire Fortegra Financial in a public merger transaction valued at approximately US$218 million.
• Front Street Re in an annuity reinsurance transaction with Bankers Life Insurance Company.
• AXA Liabilities Managers in U.S. legal and regulatory matters related to the acquisition by its investment vehicle, AXA DBIO, of the international subsidiaries of GLOBALE Rückversicherungs-AG.
• Cigna in regulatory and tax matters relating to its US$3.8 billion acquisition of HealthSpring.
• Harbinger Group in its US$350 million acquisition of Old Mutual U.S. Life Holdings.
• Hannover Re in its acquisition of the ING individual life reinsurance business from Scottish Re.
• Cerberus Capital Management in the insurance aspects of its US$14 billion acquisition of GMAC and US$7.4 billion acquisition of Chrysler Group and related financial services business from DaimlerChrysler.
• Cerberus Capital Management and MassMutual Capital in their US$600 million purchase of a controlling interest in Scottish Re.
• Stone Point Capital and Harbor Point in the formation and initial US$1.5 billion capitalization of Harbor Point Limited, a global reinsurance company based in Bermuda, and Harbor Point's acquisition of the ongoing business of Chubb Re, a subsidiary of The Chubb Corporation.
• ACE Limited in its sale of three subsidiaries–American Reinsurance Company, Brandywine Reinsurance Co. (UK) Ltd. and Brandywine Reinsurance Company S.A.–to Randall & Quilter Investment Holdings Limited.

Some of the above matters were handled prior to joining Sidley.