Benjamin Woolf is a partner in the Corporate department and leads the Structured Finance practice.

Benjamin has significant experience within the structured finance sector representing issuers and investors alike on countless structured finance transactions, including primarily, CLOs, CRE CLOs, PACE securitisations and other structured lending transactions. He frequently works on securitisation, representing issuers and underwriters in both public and private offerings of securities backed by a variety of asset classes, including residential products and trade receivables.

Benjamin is a member of Appleby’s Scholarship & Student Committee mentoring students and assisting with their formal and informal training. Benjamin also volunteers at the Legal Befrienders Clinic providing pro bono advice in the Cayman Islands for the last eight years.

Before joining Appleby in 2011, Benjamin practised in London with Clifford Chance LLP and, subsequently, as a senior associate at Mayer Brown LLP where he worked primarily on securitisation.

Other experience includes restructuring and acquisition finance as well as public equity offerings and private placements in the oil and gas sphere.


IFLR1000 2022 rates Benjamin as ‘highly regarded’ in the capital markets: debt, capital markets: structured finance and securitisation, and M&A practice areas. In 2021, Chambers Global commended Benjamin as “best in class in terms of knowledge, expertise, professionalism and responsiveness” with sources viewing him as “an exceptional banking lawyer who is versatile and can handle complex matters/transactions”. Legal 500 2021 recognised Benjamin as a ‘leading individual’ noting him as “highly responsive, pragmatic and commercial, yet extremely technical and capable of managing complex issues”. Legal 500 previously noted Benjamin as “easily the best in the industry” as well as a “a smart lawyer who works tirelessly for his clients´ interests”. In 2018, he was identified among the world´s leading capital markets lawyers by Who´s Who Legal.

Qualifications & Education

Benjamin graduated from McGill University with an LL.B and B.C.L.

He was admitted as a Solicitor and called as a Barrister to the Alberta Bar in 2004 (non-practising), as a Solicitor in England and Wales in 2009 (non-practising) and as an Attorney-At-Law in the Cayman Islands in 2011.

“[Benjamin] has a strong legal mind with commercial awareness.”

The Legal 500

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