Jonathan J. Kelly

JONATHAN KELLY is a co-leader of Sidley’s global Insurance practice, co-head of the firm’s M&A and Private Equity group in New York and Boston, and member of the firm’s Executive Committee. In 2024, he was appointed a member of the U.S. Federal Reserve Board’s Insurance Policy Advisory Committee (IPAC) for the 2025–2028 term. Jon represents insurance companies, financial institutions, investors, and regulators in transactional matters, including mergers and acquisitions, reinsurance, risk transfer, and restructuring transactions.

Strong guidance of his clients has earned Jon recognition in Chambers USA for his work in Nationwide (2020–2025) and New York (2019–2025) Insurance: Transactional & Regulatory. In the 2024 edition, clients noted that he is “fantastic” and an “incredibly talented lawyer with a deep level of experience who can consistently be relied upon to deliver best-in-class service.” Sources also praised him as “among the most knowledgeable and practical deal lawyers in the insurance space,” and that he's “very commercial, practical, and clients like him.” Jon has also been recognized by his peers for inclusion in Best Lawyers in America® for his work in Insurance Law (2015–2026).

Jon has advised on numerous transactions in the life, property and casualty, and healthcare areas, including, for example, representation of: 

• Aspida Re in its second APAC reinsurance transaction with a highly rated Japanese life insurance carrier.
• Fortitude International Reinsurance Company Ltd. in a US$4 billion reinsurance transaction with Taiyo Life.
• Fortitude Re in the reinsurance of US$3.4 billion of long-term care reserves and approximately US$120 million of individual disability insurance business from Unum.
• National Life Group in a US$4.9 billion flow and block annuity reinsurance transaction with 26North.
• The Cigna Group on insurance regulatory matters in the sale of its Medicare businesses and CareAllies to HCSC for a total transaction value of approximately US$3.7 billion.
• Global Atlantic in the reinsurance of a US$19.2 billion block of MetLife’s U.S. retail annuity and life insurance business.
• Resolution Life in a strategic transaction with Farmers New World Life Insurance Company (FNWL) involving the cession of FNWL’s in-force individual life business to Resolution Life subsidiary Security Life of Denver, a flow reinsurance treaty covering the current range of individual life products, and retrocession to Swiss Re of all of the reinsured term life liabilities.
• Fortitude Re in multiple reinsurance transactions, including block and flow transactions, with leading Japanese life insurance companies.
• Cornell Capital LLC in its acquisition of Longevity Holdings, a specialty TPA and service provider to various end markets, from an investor group led by Stone Point Capital.
• Fortitude Re in its acquisition of Plans’ Liability Insurance Company.
• Fortitude Re in its US$4 billion annuity reinsurance transaction with T&D Holdings subsidiary Taiyo Life, marking Fortitude Re’s inaugural reinsurance deal covering business in Asia.
• Venerable in its transaction with Manulife to reinsure approximately US$22 billion of variable annuity business from John Hancock.
• An investor consortium led by Cornell Capital LLC, Atlas Merchant Capital LLC, TRB Advisors LP, Global Atlantic Financial Group, Pine Brook, J. Safra Group, Hudson Structured Capital Management, and The Hartford in the sale of Talcott Resolution to Sixth Street.
• Prosperity Life in the reinsurance of US$1.7 billion of statutory reserve liabilities from National Western Life on a coinsurance with funds withheld basis.
• Global Atlantic in the reinsurance from Unum Group of a closed block of individual disability income business backed by US$8.5 billion in assets.
• Venerable in its acquisition of Corporate Solutions Life Re from Equitable Holdings, and the reinsurance of approximately US$26 billion of reserves from Equitable Financial Life Insurance Company.
• MetLife in its acquisition of Versant Health from an investor group led by Centerbridge Partners for approximately US$1.7 billion.
• GoldenTree Asset Management LP in connection with the agreement by Star Insurance Holdings LLC to acquire Syncora Guarantee Inc. for US$392.5 million.
• Fortitude Re in a high-profile deal valued at US$2.2 billion in an agreement with American International Group.
• Cigna Corporation in the insurance and healthcare regulatory matters associated with its acquisition of publicly traded Express Scripts Holding Company for approximately US$67 billion.
• Apollo Global Management, LLC and Athene Holding Ltd. in the acquisition of Voya Financial, Inc.’s closed block variable annuity business through Venerable Holdings, Inc. and Athene’s agreement to reinsure US$19 billion of Voya’s fixed and fixed indexed annuity liabilities.
• Hartford Financial Services Group, Inc. in the sale of its Talcott Resolution life insurance and annuity businesses for US$2.05 billion to an investor group that included Global Atlantic Financial Group, Cornell Capital, TRB Advisors, Pine Brook, and J. Safra Group.
• The Sellers of Jefferson National Financial Corp. and its affiliates, including Jefferson National Life Insurance Company, to Nationwide Life Insurance Company.
• Cigna Corporation in the insurance and healthcare regulatory matters associated with its terminated sale to Anthem, Inc. in a transaction valued at US$54.2 billion.
• A large private equity-affiliated life and annuity company in the potential acquisition of the U.S. life and annuity companies of a European insurer in an auction process.
• The State of South Carolina in the review of a captive financing transaction.
• One of the lead investors in a transaction in which XL Insurance (Bermuda) Ltd. entered into a definitive agreement to sell its wholly owned subsidiary, XL Life Reinsurance Ltd., to GreyCastle Holdings Ltd. for US$570 million in cash.
• Athene Holding Ltd. in its US$1.55 billion acquisition of Aviva plc’s U.S. life insurance business.
• Hartford Financial Services Group, Inc. in the sale of Hartford’s individual annuity new business capabilities to Forethought Financial Group, Inc.
• Hartford Financial Services Group, Inc. in the sale of Hartford Life International Ltd. for approximately US$285 million to Berkshire Hathaway Inc. unit Columbia Insurance Co.