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Clifford Chance

Clifford Chance
Gary Boss

Gary Boss


Gary Boss

Gary Boss has established himself as a leading transactional lawyer in the United States and globally, with particular distinction for his work in the financial services sector. Gary's experience includes domestic and cross-border M&A transactions of all types.

Gary also has substantial capital markets expertise, having worked on public company spinoffs, primary and secondary equity offerings, IPOs, tender offers, private placements, 144A offerings and contingent capital transactions.

Gary has worked in insurance sector startups and insurance rehabilitation matters, involving all major types of insurance companies, life insurers, property and casualty insurers, financial guarantee insurers and Lloyd's syndicates, as well as insurance brokerages. In the reinsurance sector, he has worked with six of the ten largest global reinsurers on M&A matters. Gary has also structured several of the most complicated reinsurance M&A transactions completed in the reinsurance sector to date. Of particular note, his work structuring the high-profile launch of Watford Re — a first-of-its-kind hedge fund reinsurance vehicle that was recently named "Capital Raise of the Year" and "Launch of the Year" by leading insurance industry magazine Reactions — engendered strong interest in the marketplace.

Gary also represents strategic and financial acquirers in various US and cross-border acquisitions and joint ventures related to financial services. He recently represented Jardine Lloyd Thompson Group plc on its acquisition of the Towers Watson reinsurance brokerage business, which was recognized by Reactions as the North American "M&A Insurance Deal of the Year."

Gary has also established strong connections with banking advisors and private equity firms focused on the insurance market, placing him at the nexus of the industry. He regularly advises senior executive and boards of directors at many global (re)insurers and in the last few years has come to be regarded as the leading industry expert in forming alternative capital insurance and reinsurance companies.

Please click here to see a list of Gary's deals.

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Contact details

Career and qualifications

  • Brigham Young University (BA Economics) 1989
  • University of Michigan (MBA) 1993
  • Yale Law School (JD) 1996
  • Admitted as an Attorney-at-Law in New York 1997

Professional bodies

  • American Bar Assocation

Awards and citations

  • Leading Lawyer
    Legal 500 USA 2020: Insurance: Non-contentious
  • Gary Boss garners praise for his adroit handling of complex transactions, formations and ventures within the insurance industry. An impressed client reports: "Besides being a terrific technical lawyer, he has also been extraordinarily responsive to all our needs and provides thoughtful guidance in all areas."
    Chambers USA 2020: Insurance: Transactional & Regulatory (New York)
  • Gary Boss serves as cochair of the firm's US insurance practice and primarily advises on the formation of insurance and reinsurance companies as well as a variety of other transactional matters. "He is like a guardian angel," comments one pleased client, adding: "He makes sure things get done."
    Chambers USA 2020: Insurance: Transactional & Regulatory (Nationwide)
  • "Gary Boss 'is a highly experienced, thoughtful adviser and has a deep knowledge of the insurance sector,' say impressed clients, and another adds: 'He is a great legal practitioner but also very commercially minded.' He is recognized for his considerable skill in handling high-value transactional matters in the insurance and reinsurance space."
    Chambers USA 2019: Insurance: Transactional & Regulatory – New York
  • "[Gary Boss] is on top of every issue and ensures high-quality advice by all involved practice areas."
    Legal 500 USA 2019: Insurance: non-contentious: Leading Lawyer
  • "Gary Boss is 'very responsive, commercial and technically sound,' report sources, with others adding: 'He advocates well for clients, is on top of the issues and is knowledgeable.' He is experienced across a spectrum of transactional matters and noted for particular skill in reinsurance-related deals. He also advises on regulatory issues."
    Chambers USA 2018: Insurance: Transactional & Regulatory – New York 
  • Leading Lawyer
    Legal 500 USA 2018: Insurance: non-contentious
  • "Gary Boss comes highly recommended for his expertise in insurance transactions, offering particular expertise in complex formations involving reinsurance entities. Sources value his 'very creative, entrepreneurial and commercial' approach to deals, as well as his 'encyclopedic knowledge of even the finest points and pragmatic solutions to seemingly complex problems.'"
    Chambers USA 2017: Insurance: Transactional & Regulatory – New York
  • Two insurance deals structured by Clifford Chance receive top industry awards