Gary Boss advises clients on a wide range of complex corporate transactions, particularly within the insurance sector.

Mr. Boss leverages strong ties with the financial services sector to represent some of the world’s largest private equity companies, hedge funds, asset managers, banks, insurers, and reinsurers on:

  • US and cross-border mergers and acquisitions
  • Reorganizations
  • Joint ventures and investments
  • Public company spin-offs
  • IPOs and direct listings
  • Primary and secondary equity offerings
  • Tender offers
  • Private placements
  • High-yield offerings
  • Contingent capital transactions
  • Sophisticated and highly structured investment product development

He combines exceptional business and legal acumen to lead companies on formation and capital raises, collectively raising more than US$14 billion on behalf of 11 companies recently, including from institutional, asset management, private equity, hedge fund, sovereign and family office investors and sponsors.

Mr. Boss plays a leading role at the forefront of corporate and strategic matters relating to insurtech and fintech and regularly garners recognition from top industry publications.

Mr. Boss’ experience includes representing:

Corporate/M&A Transactions

  • Fidelity National Information Services (FIS Global), a Fortune 500 fintech company, on its:
    • Acquisition of a majority stake in Virtus Partners, a US credit-based alternatives fund solutions provider*
    • Acquisition of Zenmonics, a provider of software solutions*
    • €375 million acquisition of Clear2Pay*
    • Sale of ClearPar to Markit*
    • US$1.8 billion acquisition of eFunds*
    • Public company spin-off*
  • Corinthian Capital on its:
    • Acquisition of Ultimate Toys Inc.
    • Acquisition of Eastern Wholesale Fence and its subsequent sale to Center Rock Capital Partners and Leelanau Private Capital*
    • Acquisition of Best Lighting Products from Wafra Partners*
    • Acquisitions of Hamilton Group and Sierra Engineering, consulting and engineering firms that serve the international oil and gas industry*
  • Watford Holdings on its:
    • US$700 million acquisition by Bermuda-based insurance, reinsurance, and mortgage insurance company Arch Capital Group*
    • Agreement to acquire French insurance company Axeria IARD from the APRIL Group*
  • AEGON on the sale of Transamerica Re to SCOR*
  • A consortium of eight private equity firms and others on Ariel Re’s sale to Goldman Sachs*
  • Armour, a Bermuda-based P&C runoff reinsurance company, on its sale of ILS Investment Management*
  • Ascendant, a Bermuda-based, publicly traded energy and energy-related services provider, on its sale to Algonquin Power & Utilities*
  • Assurant on acquiring certain insurance agencies owned by Green Tree Credit Solutions*
  • Fidelity National Financial on its:
    • Acquisition of LandAmerica Financial Services*
    • Sale of its National Flood Insurance Program business to Aquiline Capital*
    • Sale of its personal lines business to WE Holding*
    • US$400 million acquisition of InterCept*
  • FOJP’s management team on disposing Hospitals Insurance Company and certain FOJP assets to The Doctors Company*
  • Gallatin Point Capital, as lead investor, on its collective investment behind Sirius’ go-public deal*
  • Hannover Re and Benfield on the sale of alternative investment vehicles to AIG*
  • Hannover Re on the sale of its business lines to Hartford Financial Services*
  • HBK and Northaven Management on the sale of Rockhill Insurance to State Auto*
  • Jardine Lloyd Thompson Group on acquiring Towers Watson’s reinsurance brokerage unit*
  • Lender Processing Services on its public company spin-off*
  • Lincoln National on its US$7.5 billion acquisition of Jefferson-Pilot Financial*
  • MetLife on its:
    • US$11.8 billion acquisition of Travelers Life and Annuity from Citibank*
    • Sale of its 401(k) business to Great West Life & Annuity*
    • US$1.3 billion acquisition of The Midland Company*
    • US$352 million acquisition of Sterling Life and Olympic Health Management from Aon*
    • US$742 million acquisition of Hartford Steam Boiler from AIG*
  • National Atlantic Holdings on its acquisition by Palisades Safety and Insurance Association*
  • Premia Holdings on acquiring Navigators Holdings (Europe) and its associated companies, including Assurances Continentales – Continentale Verzekeringen of Belgium and Canal Re of Luxemburg, from The Hartford*
  • RenRe, Koch, and Partner Re on the sale of Channel Re to MBIA*
  • Sedgwick on:
    • The sale of its group health peer review and independent medical examination assets to ExamWorks*
    • Acquiring Stericycle's Expert Solutions service line*
    • Acquiring York Risk Services Group*
    • Malaysian subsidiary Sedgwick Malaysia’s acquisition of Maphilindo International from the existing shareholders*
    • Acquiring Security Capital Corporation*
  • Slice, an insurtech startup, on corporate and insurance regulatory matters, including multiple joint ventures with large insurers and corporates*
  • Sun Life Financial on its:
    • US$650 million acquisition of Genworth Financial’s group benefits business*
    • Sale of two operating businesses*
  • Swiss Re on its multi-jurisdictional joint venture with Orsus Insurance International*
  • THL, TPG, and other investors on their US$635 million acquisition of Sedgwick from Stone Point Capital*
  • THL, TPG, and other investors on their sale of a minority interest to United Healthcare*
  • Tower Group on various acquisition transactions*
  • Unified Commerce Group on its strategic investment in sustainable fashion brand Frank And Oak*

Other Financial Services Transactions

Transaction counsel on the formation and capital raise of large reinsurance and insurance companies, including:

  • Acra Re, a Bermudan reinsurance vehicle (approximately US$6 billion of capital raised) (backed by Apollo Global Management)*
  • Apollo Global Securities, LLC and Apollo Management Holdings, L.P. on an agreement for Apollo-affiliated insurance companies, third-party insurance managed accounts, and other institutional clients to invest US$500 million into surplus notes issued by Chesterfield Reinsurance Company, a wholly owned indirect subsidiary of Reinsurance Group of America, Incorporated
  • Arch Capital Group on its transfer of approximately US$400 million of reserves to Catalina*
  • Armour, a Bermuda-based P&C runoff reinsurance company (US$500 million of capital raised) (backed by Aquiline Capital)*
  • Ategrity Specialty Insurance Company, a specialty P&C insurance company focused on the excess and surplus lines market (approximately US$250 million of initial capital raised)*
  • A Bermuda-based permanent capital vehicle with a focus on annuities (approximately US$1 billion of capital raised) (backed by Bayview Asset Management)*
  • A Bermuda-based permanent capital vehicle with an underlying asset involving peer-to-peer lending (approximately US$500 million of capital raised) (backed by a leading ILS company)*
  • Chubb Group on integrating its insurance business following its merger with ACE*
  • Elanus Capital Management on a private placement debt investment in Conifer Holdings, a specialty insurance provider, supporting its adverse development coverage, refinancing activities, and general corporate purposes*
  • Fidelis Insurance, a specialty insurance and reinsurance company (US$1.5 billion of capital raised)*
  • Finitive, a fintech platform, on general corporate advisory work*
  • Genworth, an S&P 400 insurance company, on various potential transfers of XXX/AXXX blocks*
  • Harrington, a Bermuda-based reinsurance company (US$600 million of capital raised) (investments by AXIS Capital Holdings and The Blackstone Group)*
  • KaylaRe, a Bermuda-based reinsurance company (US$620 million of capital raised) (investments from funds managed by Hillhouse Capital Management and Stone Point Capital)*
  • Legal & General on its asset management and trading operations, joint ventures, insurance M&A, longevity de-risking, and insurance licensing and regulatory considerations*
  • Marketlend, an online lender, on general corporate advisory work*
  • MetLife on restructuring an annuity business sold to The Hartford*
  • Nomura on converting its equity shareholding in Catalina into debt*
  • Premia Re, a startup reinsurer dedicated to runoff (US$510 million of capital raised) (backed by Kelso & Company and Arch Capital Group)*
  • Premia on its:
    • Reinsurance-to-close transaction with AmTrust/Canopius*
    • Establishing a new European runoff platform with a hub in Germany*
    • Structuring and establishing a Luxembourg-based reinsurance holding company structure*
    • US$400 million loss development cover reinsurance transaction with AmTrust*
    • Retroactive reinsurance transaction with GuideOne*
    • Private placement of US$40 million subordinated notes structured to qualify as tier 2 capital*
  • Teachers Insurance and Annuity Association of America-College Retirement Equities Fund, a Fortune 100 financial services organization, on the regulatory compliance aspects of its acquisition of strategic businesses (including asset management and real estate management groups), insurance and New York not-for-profit regulatory filings, and corporate governance*
  • Universities Superannuation Scheme, one of the world's largest pensions, on its role as lead investor in a new Bermuda reinsurer (US$250 million investment of US$2 billion capital raised)*
  • Watford Holdings, a Bermuda-based multiline reinsurer that was a first-of-its kind hedge fund reinsurance vehicle (US$1.13 billion of capital raised)*
  • Watford Holdings on its direct listing of common shares on the Nasdaq Global Select Market and its offering of US$175 million aggregate principal amount of 6.50% senior unsecured notes due 2029*
  • Wells Fargo Securities, as representatives of the initial purchasers, on Fidelis Insurance Holdings’ debut issuance of US$300 million aggregate principal amount of 4.875% senior notes due 2030*

*Matter handled prior to joining Latham

Bar Qualification

  • New York


  • JD, Yale Law School, 1996
  • MBA, University of Michigan, 1993
    High Distinction
  • BA, Brigham Young University, 1989
    magna cum laude