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’s practice includes advising on mergers, acquisitions, disposals and joint ventures (particularly those involving sponsors, their portfolio companies or other private capital-owned vehicles) and regulatory matters (with a particular emphasis on U.K. and EU Solvency II). He also counsels on strategic reinsurances, schemes involving governments or multilateral institutions, restructurings and reorganisations, capital-raising transactions and material commercial agreements.

He has been repeatedly ranked in Chambers UK, where 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 partner.

Mr. Chaplin’s representations prior to joining Skadden include advising:

  • African Union/Afreximbank on the creation of the African Vaccines Acquisition Trust (AVAT) and related purchases and donations of COVID vaccinations, as well as the establishment of the related AVAT No-Fault Compensation Scheme Trust and no-fault compensation scheme covering the administration of vaccines;
  • Ageas on the:
    • sale of its London market back book to RiverStone International by means of reinsurance and a Part VII transfer;
    • disposal of its majority stake in Tesco Underwriting to Tesco;
    • acquisition of an interest in Taiping Re; and
    • sale of its U.K. commercial front book to AXA;
  • Athora on the acquisition of Vivat from Anbang;
  • Barbican Insurance Group’s management team on the sale of the company to Arch;
  • Blackstone Tactical Opportunities on the establishment with Brit of Ki, the first fully digital and algorithmically driven Lloyd’s of London syndicate;
  • Correlation Risk Partners on insurance sector investments;
  • Global Risk Partners on the acquisition of the Marsh U.K. broker networks business comprising Marsh ProBroker, Bluefin Network and Purple Partnership. The acquisition also included Marsh Connections, Marsh Labyrinth and Broker2Broker;
  • HM Government for the:
    • Department of Business, Energy and Industrial Strategy on the creation of the nuclear decommissioning fund arrangements for Hinkley Point C with EDF Energy (including associated advice to the Nuclear Liabilities Financing Assurance Board) and on the establishment of the Trade Credit Reinsurance Scheme;
    • Department of Digital, Culture, Media and Sport on the establishment of the Film and Television Restart Scheme, an indemnity scheme to cover certain COVID-related losses, and the Live Events Reinsurance Scheme, a reinsurance scheme at Lloyd’s covering the cancellation of live events for COVID-related reasons; · Department of Health and Social Care on the establishment of its Clinical Negligence Scheme for General Practice and the related assumption of back books from Medical and Dental Defence Union of Scotland (MDDUS) and Medical Protection Society (MPS), and on the English Pharmacies reinsurance scheme for the administration of COVID vaccinations; and
    • Department of Levelling-up, Housing and Communities on the establishment of the External Wall System Professional Indemnity Insurance Scheme with SCOR and MGA Mutual for external wall system assessors, and on the creation of building safety developer remediation contracts;
  • Legal & General (L&G) on:
    • its disposal to ReAssure of its mature savings business by means of reinsurance and a Part VII transfer;
    • a variety of pension risk transfer transactions and related reinsurances; and
    • Solvency II matters, including the establishment of its real estate, FX bond and equity release mortgage matching adjustment transformation vehicles, and on its arrangements involving its U.S. operations and L&G Re;
  • Lucida Broking Holdings on the investment in the company by Lloyds Development Capital and associated debt facility entered into with Ares;
  • Markerstudy on:
    • its arrangements with Qatar Insurance Company (QIC);
    • the investment into the company by Pollen Street Capital, CVC Capital Partners and QIC and associated debt facilities with CVC;
    • the acquisition of Lloyd’s broker Clegg Gifford & Co.; and
    • its purchase of BGLi and associated equity and debt financings with Pollen Street Capital and CVC;
  • Medical & Commercial International on:
    • its management buyout from Castel Underwriting Agencies; and
    • the establishment of its syndicate at Lloyd’s with Asta;
  • Pollen Street Capital on the acquisition of Tradex Insurance Company;
  • Quartz, the owner of the Granite broking business and Haven insurance carrier, on the creation of the group, the investment into the group by Inflexion and on its debt facilities with Investec;
  • RiverStone International on the:
    • purchase of the Lloyd’s business Neon from American Financial Group, including the Lloyd’s members GAI Indemnity, Lavenham Underwriting, Sampford Underwriting and Syndicate 2468;
    • reinsurance to close (RITC) transaction for 2017 and prior years of Syndicate 1200 at Lloyd’s, managed by Argo Global; and
    • split RITC for 2019 and prior years with MS Amlin’s Syndicate 2001 at Lloyd’s;
  • Rothesay Life on the establishment of asset vehicles;
  • Signature Aviation on the sale of its OEM-licensed parts business ONTIC to CVC Fund VII, and on the takeover of Signature by a consortium comprising Blackstone, Global Infrastructure Partners and Cascade;
  • UNICEF on:
    • the establishment of a no-fault compensation scheme for the administration of COVID vaccinations (the Covid-19 Vaccine Facility No-Fault Compensation Scheme);
    • a joint instruction with the World Bank for the issuance of an award-winning donation-backed bond to fund vaccination programs (IFLR Deal of the Year 2022: debt and equity-linked); and
    • on a variety of insurance-related projects and schemes;
  • the Welsh government on the establishment of its clinical negligence scheme for general practitioners and the related assumption of back books from MDDUS and MPS;
  • on pension derisking transactions for 3i, Monsanto and PA Consulting; and
  • numerous insurers on prudential solvency and group structuring matters in the U.K., Gibraltar, Europe and Bermuda.

Mr. Chaplin has written and spoken extensively on insurance matters. In his prior role, he also was responsible for Solvency II publications, including the creation of a market-leading guide and app, and a series of related podcasts.



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


  • England & Wales

Robert A. Chaplin

Partner, Insurance; Mergers and Acquisitions; Private Equity