Jeffrey S. MacDonald

With experience structuring, negotiating, and closing complex acquisitions and divestitures of regulated insurance companies, brokerages, and in-force and run-off blocks of business, Jeffrey 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.

Insurance Company Transactions

• 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 U.K. 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 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

Other Transactions

• 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 U.K. investment bank in its sale of a U.S.-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