International Arbitration
Cayman Islands
12 November 2025
Appleby’s Cayman Islands insurance and reinsurance practice advises on all aspects of insurance law and regulation, acting for insurers, reinsurers, cedants, and other market participants. The team has extensive experience establishing new entities as captive insurers, reinsurers, and direct or domestic insurers, and regularly assists with reinsurance treaty negotiations. Co-head Simon Raftopoulos advises on a wide range of corporate finance transactions, including significant mandates for insurance and reinsurance clients, while co-head Jacob MacAdam frequently handles major insurance and reinsurance transactions, bringing deep regulatory expertise to complex matters across the sector.
Legal 500 Editorial commentary
Testimonials
Collated independently by Legal 500 research team.
‘Appleby is a go-to firm for complex financings, property, and high-net-worth structuring, with strong corporate and disputes support. Unlike peers more narrowly focused on investment funds, Appleby offers clients a broader, full-service platform enhanced by its cross-border regulatory expertise.’
‘In Cayman, Menelik Miller and Jacob MacAdam stand out in regulatory matters for their technical precision combined with highly practical, solution-oriented advice. Our clients value their ability to navigate CIMA requirements smoothly and to anticipate regulatory concerns.’
‘Jacob McAdam really gets to know you and your business's needs on a personal level. He is involved and overseeing every engagement rather than being a figurehead and relying on associates for work product. Menelik Miller is the best technical lawyer I've met.’
Key clients
- Greenlight Re
- Brookfield Asset Management
- Cayman Islands Reinsurance Companies Association (CIRCA)
- Oceanview Secure Reinsurance Limited
- Argus
Work highlights
Acted as Cayman counsel to Brookfield Asset Management, the world’s largest asset management company, in connection with the establishment of a significant Cayman Islands reinsurer.
Act as retained Cayman Islands legal counsel to the Greenlight Group. We provide ongoing financial regulatory advice on all aspects of CIMA compliance with a particular focus on corporate governance, outsourcing arrangements, and contractual matters.
Acted as Cayman Islands and Bermuda counsel to GeoVera Investment Group, Ltd., a specialty property insurance group, in connection with the sale of its managing general agent business (GeoVera MGA) to U.S.-based insurance managing agent SageSure, by way of a statutory merger.
Practice head
Simon Raftopoulos; Jacob MacAdam
Other key lawyers
Dean Bennett; Menelik Miller; Miriam Smyth; Vance Power