Litigation
Cayman Islands
19 August 2025
As part of its offering across offshore markets globally, the Cayman Islands office at Appleby assists insurance and reinsurance clients with corporate, financing and regulatory matters. Simon Raftopoulos and Jacob MacAdam, whose practice encompasses advising on insurance transactions and regulatory matters particularly in the reinsurance, banking and fiduciary space. Menelik Miller is sought out by insurers, reinsurers, investment companies and fintech clients for her expertise in regulatory issues including license applications, registrations, authorisations, notifications and regulatory filings, areas in which Miriam Smyth is also notably active.
Legal 500 Editorial commentary
Testimonials
Collated independently by Legal 500 research team.
‘I find the Appleby team to be incredibly helpful when faced with contentious matters. I have obtained advice from them ranging from general day to day corporate matters through to more complicated and controversial matters and in all circumstances the team has come through with thorough and clear advice to see their clients through to a solution. The team is very collaborative, helpful, and most important practical in understanding the end goal of their clients and helping them find the best path forward.’
‘Jacob MacAdam is a pleasure to work with. Of course he is extremely knowledgeable and responsive but beyond that he exhibits a level of professionalism that makes him stand out against his competitors. I value his advice as a legal professional and industry colleague and I do not hesitate to recommend him to anyone in the insurance industry seeking legal advice as I have full confidence in his advice.’
‘The team stands out for delivering expert and reliable guidance firmly rooted in regulatory requirements through a deep understanding of governmental principles ensuring that clients receive insightful advice fully compliant with relevant authorities.'
- 'A key strength is the practice's ability to balance urgency with prudence. Responsive to time-sensitive matters, driving projects forward efficiently without compromising on thoroughness or pushing beyond appropriate boundaries. This approach resonates with clients who value both timeliness and diligence.'
- 'The team is knowledgeable, trustworthy, and delivers timely service for clients navigating intricate regulatory landscapes.’
‘They answer questions with revenant and informed replies. No hesitation to give a straight forward response that is actionable. If they need more time to research the question, that’s said and the reply is timely. Competent, knowledgeable, and direct. Without hesitation and with praise I recommend the individuals that I work with at the firm.’
Key clients
- Greenlight Reinsurance
- TxEx Energy Investments, LLC –
- Brookfield Asset Management
- Blue Ocean Reinsurance Group
Work highlights
Advising Greenlight Reinsurance on ongoing regulatory compliance with Cayman regulatory laws, regulations, rules and guidance issued by CIMA.
Advised a health care provider on obtaining a Class A insurance issued by the Cayman Islands Monetary Authority.
Assisted Blue Ocean Solutions with developing a suite of bespoke regulatory policies and procedures both for its own offering and its clients.
Practice head
Simon Raftopoulos; Jacob MacAdam
Other key lawyers
Menelik Miller; Miriam Smyth