Jeffrey S. MacDonald represents global securities issuers, investment funds, and strategic buyers and sellers across industries in connection with mergers and acquisitions (M&A), investments, divestitures, private equity and debt financings, and general corporate and governance matters. With a focus on insurance and financial services industry transactions, Jeff has experience structuring and negotiating private equity-sponsored leveraged buyout transactions, strategic acquisitions and divestitures, joint ventures, equity and debt portfolio investments, and recapitalizations, and managing the formation, financing, and licensing of new market entrants.
With experience structuring, negotiating, and closing complex acquisitions and divestitures of regulated insurance companies, brokerages, and in-force and run-off blocks of business, Jeff regularly handles major and middle-market insurance company and insurance brokerage transactions and financings and mutual company affiliations, both domestically and in cross-border transactions. In addition to the insurance industry, Jeff also represents clients across the financial services and technology sectors.
Insurance Company Transactions
Represented the board of directors of NORCAL Mutual Insurance Co., a provider of medical professional liability insurance and risk management solutions to physicians, medical groups, hospitals, clinics, and allied healthcare, in its $450 million sale to ProAssurance Corp.
Represented Tokio Marine Kiln in the sale of interest in NAS Insurance Services, a managing general agency, to Houston Casualty Company
Represented Tokio Marine Kiln in its investment in Journey Insurance Company which will focus on offering homeowners’ and commercial residential property insurance in Florida, Texas, and South Carolina
Represented Tokio Marine Kiln Group in its acquisition of WNC Holding Co, a holding company for insurance service providers
Represented Randall & Quilter Investment Holdings in the acquisition of United States Sports Insurance Company, a Washington, DC captive of USA Swimming, Inc.
Represented a New York private equity fund as co-lead investor in connection with $575 million of committed equity investments in Essent Group Ltd., a Bermuda-based startup mortgage guaranty insurer and reinsurer
Counseled Essent Guaranty in its acquisition of an operating platform and related intellectual property from Triad Guaranty
Advised PartnerRe Ltd. in its strategic acquisition of a significant minority interest in Entitle Insurance Company, a direct to consumer title insurance provider
Represented Guardian Life Insurance Company in its acquisition of Premier Access Insurance Company, a California-based dental insurer with affiliated clinical and off-shore servicing operations
Represented Guardian Life Insurance Company in its acquisition of Reed Group Ltd., a leading provider of absence management services
Represented a New York-based private equity fund in its acquisition of two Rhode Island homeowners insurers through tranched investments of up to $200 million
Advised a UK insurance company in its assumption of a $100 million run-off block of lead paint business through reinsurance by a Bermuda SPI affiliate, and related policy administration arrangements and senior secured debt financing
Represented a New York-based private equity fund in its $127.5 million leveraged acquisition of a self-insurance group administration business, and related senior secured debt financing
Counseled United Guaranty Corporation, an AIG affiliate, in the sale of its Israeli mortgage guaranty subsidiary to a leading Israel domiciled insurer
Represented Tower Group, Inc. in the acquisition of the in-force and renewal personal lines business from One Beacon, including the acquisition of stock subsidiaries and reciprocal exchange administrators and related reinsurance and administrative services arrangements
Advised a New York private equity fund, as lead investor in the formation and financing of a new Bermuda holding company and the acquisition of Oceanus Reinsurance SA, a Puerto Rico cell reinsurer
Represented Patrons Mutual and Litchfield Mutual in their affiliation transactions and reinsurance pooling arrangements with State Automobile Mutual Insurance Company
Represented NLC Insurance in its affiliation transaction and reinsurance pooling arrangements with Hingham Mutual Fire Insurance Company
Counseled Higham Mutual Fire Insurance Company in the sale of Casco Indemnity to Ohio Mutual Insurance Company
Insurance Agency Transactions
Represented Aspen Insurance in the sale of its US and UK surety operations to Amynta Group
Represented GoodWorks Insurance in the sale of Goodworks Financial Group to Assured Partners
Represented Aspen Insurance Holdings Limited in the $68.4 million sale of AgriLogic Insurance Services, a company which provides crop insurance, risk management, and grain marketing expertise, to CGB Diversified Services, Inc.
Represented Aspen Insurance Holdings in its acquisition of AgriLogic Insurance Services, a leading national crop insurance managing general agency and consulting business
Counseled Kiln Group Ltd., a UK underwriter, in its equity and mezzanine debt investment in the $102.5 million leveraged acquisition of WNC Insurance Services, a national specialty insurance broker
Represented GCP Capital Partners in its $57 million leveraged acquisition of Southwest Risk, a Texas wholesale insurance broker, and related senior secured debt financing
Advised Liberty Mutual Insurance in the sale of its captive commercial lines agency business in three simultaneous transactions to AJ Gallagher & Co., Hub International and USI
Represented a Chartis Insurance affiliate in the simultaneous acquisition of Maksin Group, a New Jersey student health insurance MGA, and the related acquisitions of Pearce and Pearce and Macori, Inc., two student health insurance brokerage businesses
Counseled G.S. Chapman Insurance in its sale to AJ Gallagher & Co.
Advised All Risks, Ltd in the sale of Collectibles Insurance Services to Global Indemnity Insurance
Represented a startup reinsurance broker and risk/capital management adviser in connection with $152.5 million of committed equity investments from a New York-based private equity fund
Represented GoodWorks Insurance, a startup Connecticut insurance agency, in its formation and initial and follow-on equity and debt financings
Advised GoodWorks Insurance in its acquisitions of multiple Connecticut and Massachusetts agency businesses, including Scranton and Johnson Insurance Agency; Steffen, James & Finnegan Insurance Agency; New Milford Insurance Agency and F.W. Postemski Insurance Agency
Represented the Oregon Insurance Department in connection with its review and approval of the joint venture between Moda Health Plan and Delta Dental of California. DDC invested $152 million of new equity capital for a 49.5% interest in Moda Health Plan’s parent company
Advised East Rock Capital in its equity co-investment in the acquisition by Global Atlantic (through a $9 billion reinsurance transaction) of Talcott Resolution’s fixed annuity business from The Hartford
Represented Sirius Global Solutions in the sale and proposed redomestication of Ashmere Insurance Company, a broadly-licensed Illinois domestic shell company.
Represented a New York-based private equity fund in the formation and financing of a credit card collections law firm roll-up vehicle and related services company, and the leveraged acquisition of three leading national collections firms
Represented a UK investment bank in its sale of a US-based broker-dealer
Represented a Massachusetts registered investment advisor, in its $100 million sale to a French multinational bank
Represented Renaissance Investment Group, a Massachusetts registered investment advisor, in its sale to Legacy Bank
Represented a New York-based private equity fund in the $85 million senior secured debt recapitalization of a portfolio company and related dividend, holding company formation, share exchange and $70 million delayed draw acquisition financing for a leveraged follow-on acquisition
Represented an international credit card company in its $21 million acquisition of a financial services industry research and advisory business
Represented a Connecticut-based multinational insurance and financial services company in strategic acquisition of a distributor of annuities and other financial products, as well as preferred equity investments, in two early-stage insurance industry technology companies
Represented a French multinational insurance company in the acquisition of an Ohio-based engineering and risk management consulting business
Represented a healthcare industry software development company in its Delaware reincorporation, preferred stock financings and software licensing arrangements
Brooklyn Law School, 1998, Juris Doctor
Dickinson College, 1995, Bachelor of Arts
US District Court for the Southern District of New York
Awards and Affiliations
Rising Star, IFLR1000 Financial and Corporate (2014, 2017–2021)
Rising Star, IFLR1000 United States (2018, 2019)
Ranked, Corporate/M&A, Connecticut, Chambers USA (2018, 2019)