Robert A. Chaplin

Robert A. Chaplin

Partner, Insurance; Mergers and Acquisitions; Private Equity
Robert Chaplin focuses primarily on transactional and advisory work in the insurance sector.


Mr. Chaplin advises on international and domestic mergers, acquisitions, disposals, joint ventures and strategic reinsurances. He has extensive experience in transactions involving financial sponsors and their in-house (re)insurers, portfolio companies and other private capital-owned vehicles. His clients include a diverse range of multinational, U.K., European and Bermudian insurers, reinsurers, brokers and intermediaries, including well-known participants in both the Lloyd’s and London Market. Mr. Chaplin also counsels on emerging and long-standing regulatory issues and developments in the sector (with a particular emphasis on prudential matters, including Solvency II), schemes, restructurings and reorganizations, capital-raisings, life and non-life portfolio transfers, longevity transactions, and distribution and other material commercial agreements. In addition to his extensive transactional and advisory insurance practice, Mr. Chaplin works closely with Skadden’s international litigation and arbitration practitioners in London and around the world in advising insurers, reinsurers and other market players on complex, high-stakes reinsurance disputes.

He has been repeatedly ranked in Chambers UK, in which clients note that he is “incredibly pragmatic in his approach to complex issues,” as well as “innovative, hard-working and very knowledgeable.” He also has been named a Key Lawyer in The Legal 500 UK. Before joining Skadden, he worked at a Magic Circle firm in London for 25 years, including for over 16 years as a partner.

His experience since joining Skadden includes advising:

  • Corebridge Financial, Inc. on the £460 million sale of its U.K. life insurance business to Aviva plc
  • the founders of Markerstudy Group on the £1.27 billion merger of Markerstudy with Ardonagh’s personal lines broking business, Atlanta
  • Intact Financial Corporation and its subsidiary Royal & Sun Alliance Insurance Limited in their US$648 million acquisition of the brokered commercial lines operations of Direct Line Insurance Group plc
  • BlackRock on its acquisition of Kreos Capital Management, a London-based venture and growth debt provider
  • The Special Committee of the Board of Directors of SiriusPoint Ltd. (Bermuda) on its successful defense of an unsolicited take-private approach by Daniel Loeb, the chief executive officer of Third Point LLC
  • Pinnacle Pet Group Limited on its acquisition of Animal Friends Insurance Services Limited from Correlation Risk Partners, as well as in relation to Pinnacle Group’s joint venture with Correlation Risk Partners to acquire Waggel Limited, Vet-AI, Biscuit Pet Care, Kozoo and other pet insurance companies. The combined transactions have an enterprise value of £900 million
  • Intact Financial Corporation and its subsidiary Royal & Sun Alliance Insurance Limited on the sale of its retail motor insurance business to Atlanta Group Limited, a member of The Ardonagh Group
  • U.K.-, Gibraltar- and Bermuda-based insurers on a series of regulatory capital issuances (Tier 1, Tier 2, Tier 3 and Tier 2 Ancillary Own Funds)
  • a financial sponsor on the purchase of an insurance group with business in Bermuda, the U.K. and the U.S.
  • a U.K.-based insurance business on the purchase of a Gibraltar-based insurance business and renegotiation of related commercial matters
  • Bermuda-based reinsurers on U.K. onshoring/authorization issues
  • U.K.-, Europe- and Bermuda-based reinsurers in relation to large-scale reinsurance disputes

Prior to joining Skadden, Mr. Chaplin advised a broad range of insurers, reinsurers, financial sponsors, government bodies and multilateral international organizations on a variety of transactional and regulatory matters. He represented clients such as Ageas, Athora, Barbican Insurance, Blackstone, Correlation Risk Partners, Global Risk Partners, HM Government, Legal & General, Markerstudy, Medical & Commercial International, Pollen Street Capital, RiverStone International and Rothesay Life.

Mr. Chaplin writes and speaks extensively on insurance matters. He is responsible for the firm’s "The Standard Formula" insurance newsletter and podcasts, which focus on Solvency II and related matters.



  • M.A., Cambridge University, 1999
  • L.P.C., College of Law, Guildford, 1997
  • B.A., University of Cambridge, 1996


  • England & Wales

Robert A. Chaplin

Partner, Insurance; Mergers and Acquisitions; Private Equity