Derek Stenson is a Partner in the Cayman Islands Corporate practice and advises on a broad range of corporate, finance and regulatory matters involving Cayman Islands companies and partnerships.

In the finance arena Derek acts for lenders, borrowers and sponsors on hedge fund and private equity financings, insurance and reinsurance company financings and a variety of secured cross-border transactions.  Derek has extensive experience advising a wide range of international financial and insurance institutions on all aspects of insurance and reinsurance law and regulation. Derek also has particular expertise advising on repackagings and collateralized loan obligations, corporate finance and M&A transactions, portfolio transfers, restructurings, stock exchange listings, mergers, migrations, contractual negotiations and regulatory and compliance matters.

Derek has been consistently ranked as a recommended Lawyer in Legal 500 since 2014. Clients highlight him having “outstanding knowledge, responsiveness and collaboration with other advisors”. They also note that he is “intelligent, diligent, responsive and hardworking”.



Professional Background

  • Senior Counsel at a preeminent Cayman Islands law firm
  • Associate, William Fry, Ireland

Bar Admissions

  • Cayman Islands, Attorney at Law, 2011
  • Ireland, Solicitor, 2006

Awards & Accolades

  • Recognised in the 2023 edition (and since 2022) of Chambers Global (corporate and finance)
  • Recognised in the 2024 edition (and since 2014) of The Legal 500 Caribbean (insurance and reinsurance)
  • Recognised in the 2024 edition of The Legal 500 Caribbean (banking, finance and capital markets; regulatory and compliance)
  • Recognised in the 2019 edition of The Legal 500 Caribbean (corporate and commercial)


  • Insurance Sub-Committee of Cayman Finance
  • Reinsurance Sub-Committee of Cayman Finance
  • Marketing Committee of Insurance Managers Association of the Cayman Islands
  • Editorial Board of Captive Insight