
With an exceptional breadth of experience spanning over four decades in judicial, academic, and advisory roles across Bermuda, the Cayman Islands, and the wider Caribbean, Justice Kawaley brings invaluable expertise to our chambers.
Currently serving as a Justice of Appeal on Bermuda’s Court of Appeal and as a Judge of the Grand Court of the Cayman Islands, Justice Kawaley has had a distinguished judicial career marked by landmark rulings and a deep commitment to the rule of law. His previous roles include Chief Justice of the Supreme Court of Bermuda from 2012 to 2018 and Acting Justice of Appeal for the Eastern Caribbean Court of Appeal.
Internationally recognised for his expertise in cross-border insolvency, commercial litigation, trust law, and constitutional matters, Justice Kawaley has presided over high-profile cases such as Singularis Holdings Ltd v. PwC and Re Latam Finance. His recent work in developing international cooperation principles in insolvency and judicial independence underscores his global perspective.
Beyond his judicial accomplishments, Justice Kawaley is a leading voice in legal scholarship, with extensive publications on offshore legal systems and contributions to key titles in the field. He is also an Honorary Bencher at Middle Temple and actively participates in professional organisations like INSOL International, where he is involved in the ADR Colloquium, and the International Insolvency Institute.
Justice Kawaley commented on his appointment: “I am delighted to join South Square, a chambers renowned for its excellence in insolvency and commercial law. I look forward to contributing to their ADR services and working alongside such esteemed colleagues.”
Head of Chambers Tom Smith KC added: “Hon. Justice Ian Kawaley joining as a member of our ADR team strengthens South Square’s commitment to legal excellence. His unparalleled experience and global perspective make him a valuable addition to our international practice.”
Click here for Hon Justice Ian Kawaley’s full profile.
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