Robert W. Stirling

Robert W. Stirling

Partner, Insurance; Financial Institutions

Robert Stirling focuses on insurance and asset management matters, as well as the regulatory issues involved in transactional work and the insurance sector generally. He advises on public and private acquisitions, private equity investments, portfolio and other risk transfers, share offerings and asset disposals.


Mr. Stirling also has handled numerous representations for clients such as Phoenix Group, Mitsui Sumitomo Insurance Co., Endurance Specialty Holdings, Prudential plc, Marsh and TDR Capital.

Mr. Stirling is recognised as a leading individual in non-contentious insurance in Best Lawyers in the UK, IFLR1000, The Legal 500 UK and Chambers UK, which cites his “sophis­ticated transactional insurance practice” and quotes clients saying: “He has gravitas, he’s pragmatic and he can think his way out of difficult problems. He’s a standout.”

Prior to joining Skadden in 2014, Mr. Stirling was head of the non-contentious insurance practice at a Magic Circle firm.

Mr. Stirling also has advised financial institutions on transactional and regulatory matters, including Barclays Capital, BNP Paribas and Credit Suisse.

His recent representations include advising:

  • Phoenix Group Holdings in its:
    • £2.9 billion acquisition of Standard Life Assurance Limited from Standard Life Aberdeen plc; and
    • acquisition of Abbey Life from Deutsche Bank AG for £935 million, in respect of the transaction documentation and the connected rights issue;
  • The Travelers Companies, Inc. in its US$490 million acquisition of Simply Business from Aquiline Capital Partners LLC, and subsequent reorganisation;
  • XL Catlin in its acquisition by AXA for US$15.3 billion;
  • TDR Capital LLP and MGM Advantage Holdings Limited in the sale of the MGM group of companies to Canada Life;
  • Gryphon Group Holdings in its £180 million financing and acquisition of the Guardian life insurance brand;
  • Mitsui Sumitomo Insurance Co., Ltd. (part of the MS&AD Group) in:
    • its takeover of Amlin for £3.5 billion; and
    • various internal matters, including the combination of its two Lloyd’s syndicates and the reorganisation of its Lloyd’s businesses;
  • Endurance Specialty Holdings Ltd. in its:
    • US$6.3 billion acquisition by Sompo Holdings, Inc. (this transaction was named a 2017 Deal of the Year by Asia Business Law Journal); and
    • £1.2 billion acquisition of Montpelier Re Holdings Ltd.;
  • XL Group plc in its £2.6 billion acquisition of Catlin Group Limited. The combined business is expected to have a leading presence in the global specialty insurance and reinsurance markets;
  • Calera Capital in its acquisition of RFIB Group Limited; and
  • a French insurance provider in its sale of an insurance broker subsidiary in the U.K.



  • University of Cambridge
  • The College of Law, Guildford


  • Solicitor of the Supreme Court of England and Wales

Robert W. Stirling

Partner, Insurance; Financial Institutions