Robert Stirling focuses on insurance and asset management matters, as well as the regulatory issues involved in transactional work and the insurance sector generally.


Mr. Stirling advises on public and private acquisitions, private equity investments, portfolio and other risk transfers, share offerings and asset disposals, and has handled numerous representations for clients such as Prudential plc, Marsh and TDR Capital.

Mr. Stirling’s experience also includes advising financial institutions, including Barclays Capital, BNP Paribas and Credit Suisse on transactional and regulatory matters.

His recent representations include advising:

  • Phoenix Group on its acquisition of Abbey Life from Deutsche Bank AG for £935 million, in respect of the transaction documentation and the connected rights issue;
  • Mitsui Sumitomo Insurance Co., Ltd. (part of the MS&AD Group) on its takeover of Amlin for £3.5 billion;
  • Mitsui Sumitomo Insurance Co., Ltd. on various internal matters, including the combination of its two Lloyd’s syndicates and the reorganisation of its Lloyd’s businesses;
  • Endurance Specialty Holdings Ltd. on its pending US$6.3 billion merger with Sompo Holdings, Inc.;
  • XL Group plc in its US$4.2 billion acquisition of Catlin Group Limited. The combined business is expected to have a leading presence in the global specialty insurance and reinsurance markets;
  • Mitsui Sumitomo Insurance Co., Ltd. in its US$5.3 billion acquisition of Amlin plc;
  • Calera Capital in its acquisition of RFIB Group Limited;
  • Endurance Specialty Holdings Ltd. in its US$1.8 billion acquisition of Montpelier Re Holdings Ltd.;
  • Pearl Group in its acquisition by Liberty International Holdings for just under £1 billion and its subsequent premium listing as Phoenix Group Holdings on the London Stock Exchange (prior to joining Skadden); and
  • Rothesay Life in its £1.9 billion insurance of RSA’s pension liabilities (prior to joining Skadden).

Chambers UK ranks Mr. Stirling as a leading lawyer, citing sources who stated that “he knows the insurance industry incredibly well and has great depth and breadth of experience. He is also utterly superb in a crisis — very measured and calm.” In addition, he is recognised by The Legal 500 UK. Prior to joining Skadden in 2014, Mr. Stirling was head of the non-contentious insurance practice at a Magic Circle firm.



  • University of Cambridge
  • The College of Law, Guildford


  • Solicitor of the Supreme Court of England and Wales

Robert W. Stirling

Partner, Insurance; Financial Institutions