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, 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

• MDAdvantage, a New Jersey based medical professional liability insurance company, in its sale to Mag Mutual Insurance
• Tokio Marine Kiln in the sale of Tokio Marine Highland’s US construction division to Intact Insurance Group USA LLC
• Aegis Financial, a financial marketing organization providing annuity, life insurance, retirement and business solutions to independent insurance professionals, financial advisors and their clients, in its sale to Integrity Marketing Group
• Pie Carrier Holdings in its acquisition of Western Select Insurance, a property/casualty insurance company licensed in Illinois, California, and New York, from a subsidiary of Premia Holdings Ltd.
• 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. 
• Tokio Marine Kiln in the sale of interest in NAS Insurance Services, a managing general agency, to Houston Casualty Company
• 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 
• Tokio Marine Kiln Group in its acquisition of WNC Holding Co, a holding company for insurance service providers 
• Randall & Quilter Investment Holdings in the acquisition of United States Sports Insurance Company, a Washington, DC captive of USA Swimming, Inc.
• 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
• Essent Guaranty in its acquisition of an operating platform and related intellectual property from Triad Guaranty
• PartnerRe Ltd. in its strategic acquisition of a significant minority interest in Entitle Insurance Company, a direct to consumer title insurance provider
• 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
• Guardian Life Insurance Company in its acquisition of Reed Group Ltd., a leading provider of absence management services
• A New York-based private equity fund in its acquisition of two Rhode Island homeowners insurers through tranched investments of up to $200 million
• 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
• 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
• United Guaranty Corporation, an AIG affiliate, in the sale of its Israeli mortgage guaranty subsidiary to a leading Israel domiciled insurer
• 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
• 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
• Patrons Mutual and Litchfield Mutual in their affiliation transactions and reinsurance pooling arrangements with State Automobile Mutual Insurance Company
• NLC Insurance in its affiliation transaction and reinsurance pooling arrangements with Hingham Mutual Fire Insurance Company
• Higham Mutual Fire Insurance Company in the sale of Casco Indemnity to Ohio Mutual Insurance Company

Insurance Agency Transactions

• Aspen Insurance in the sale of its US and UK surety operations to Amynta Group
• GoodWorks Insurance in the sale of Goodworks Financial Group to Assured Partners
• 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. 
• Aspen Insurance Holdings in its acquisition of AgriLogic Insurance Services, a leading national crop insurance managing general agency and consulting business
• 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
• GCP Capital Partners in its $57 million leveraged acquisition of Southwest Risk, a Texas wholesale insurance broker, and related senior secured debt financing
• 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
• 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
• G.S. Chapman Insurance in its sale to AJ Gallagher & Co.
• All Risks, Ltd in the sale of Collectibles Insurance Services to Global Indemnity Insurance
• 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
• GoodWorks Insurance, a startup Connecticut insurance agency, in its formation and initial and follow-on equity and debt financings
• 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

• Aegis Financial, a financial marketing organization providing annuity, life insurance, retirement and business solutions to independent insurance professionals, financial advisors and their clients, in its sale to Integrity Marketing Group
• 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
• 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 
• Sirius Global Solutions in the sale and proposed redomestication of Ashmere Insurance Company, a broadly-licensed Illinois domestic shell company.
• 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
• A UK investment bank in its sale of a US-based broker-dealer
• A Massachusetts registered investment advisor, in its $100 million sale to a French multinational bank
• Renaissance Investment Group, a Massachusetts registered investment advisor, in its sale to Legacy Bank
• 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
• An international credit card company in its $21 million acquisition of a financial services industry research and advisory business
• 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
• A French multinational insurance company in the acquisition of an Ohio-based engineering and risk management consulting business
• A healthcare industry software development company in its Delaware reincorporation, preferred stock financings and software licensing arrangements