Norman Klein, Cayman Managing Partner said, “It is wonderful that so many of our lawyers have been recognised by The Legal 500. I would like to congratulate them all on their inclusion and thank each member of the team for their continued dedication and hard work.  We are especially pleased with our Tier 1 appointment in Banking, Finance and Capital Markets which accurately reflects our position as market-leaders in this area. Very grateful to our clients and counterparts for allowing us the privilege to work with them.”

The team were praised in client testimonials for their excellent capabilities and exceptional level of responsiveness:

‘Always super professional and chiefly concerned with developing long-term relationships with their clients.’

‘Collaboration within and with outside partners is second to none, ensuring their clients receive the best when it comes to strategic structuring of the deals, foresight, and timeliness.’

‘Extremely knowledgeable and practical.’

‘The Appleby team are incredibly responsive and work well under pressure.’

‘Great people who know their stuff and are very well-connected in Cayman.’

‘Excellent strength across the whole team, no weak links. Collaborative and client focused, attention to detail and maximising deliverables.’

Highlights from Legal 500

Banking, Finance & Capital Markets, Corporate & Commercial:

Steered by private equity specialist Simon Raftopoulos and structured finance lead Benjamin Woolf, Appleby is routinely sought out by a deep roster of blue-chip underwriters, which turn to the firm for its significant position in CLOs, SPACs, and lender-side fund financing deals. Liesl Richter is a key port of call for clients seeking assistance with respect to CLO transactions, subscription financings, and debt and equity offerings. Jacob MacAdam‘s broad practice encompasses leveraged buyouts and capital markets deals, while Caroline Barton is noted for her expertise in aircraft and vessel financings. Georgina Pullinger regularly works with a litany of major financial institutions on cross-border lending transactions, while global SPACs co-chair Dean Bennett underpins the team’s equity offerings practice.

Real Estate

Drawing significant praise on account of its ‘sound knowledge and tremendous care‘ with clients, the ‘phenomenal‘ team at Appleby handles a formidable volume of high-value commercial, hotel and resort, residential and infrastructure-based developments, unrivalled in the Cayman Islands. The ‘preeminent‘ Norman Klein possesses decades of experience in real estate and financing matters, acting for a number of leading banks, hoteliers and property developers on all manner of deals. Adam Johnson also draws superlative praise from clients for his ‘incredibly knowledgeable and responsive‘ real estate practice, particularly in relation to tourism sector ventures and large-scale infrastructure ventures. ‘Fantastic‘ senior associate Tim Swallow is noted for his expertise in commercial leasing matters.

Trusts/Private Client

Drawing on a global network of offices that spans from the Channel Islands to Hong Kong, Appleby regularly works with a litany of high-net-worth clients on multi-jurisdictional trust disputes, including trials taken before the Grand Court. On the non-contentious side, the team is also well-versed in cross-border trust formations, structurings, and general administration matters. Global group head Carlos De Serpa Pimentel is a veteran trust litigator with considerable experience in hostile beneficiary and trustee disputes, restructuring proceedings, and contentious estate and probate matters. Sebastian Said is regarded for the depth of his contentious trusts practice, with recent highlights including big-ticket proceedings brought in the Financial Services Division of the Grand Court. Counsel Esmond Brown focuses on the establishment and administration of Cayman Islands trusts and foundation companies.

Dispute Resolution

Appleby‘s ‘excellent strength across the whole team‘ ensures that it is sought out by a stellar lineup of international corporate clients for representation in high-stakes fund disputes, winding up proceedings, and contractual enforcement matters. Newly appointed practice chair Tony Heaver-Wren has most recently helmed a number of contentious insolvencies and restructurings, appearing on behalf of clients in schemes of company arrangement and contested liquidation hearings. The ‘standout‘ Sebastian Said is widely regarded for his advocacy in international commercial litigation, with recent engagements including hostile trust proceedings and defending insurance claims before the Cayman courts. David Lee regularly handles big-ticket investment fund disputes for various foreign clients, while counsel Andrew Jackson is noted for his expertise in appraisal actions. Counsel* David Lewis-Hall is also recommended and former practice head Peter McMaster KC still contributes to the practice.


With a particularly active reinsurance practice, Appleby works with a variety of blue-chip international entities on a mix of corporate, financing and regulatory matters. Practice head Simon Raftopoulos‘ recent highlights include cross-border compliance reviews and credit facility negotiations, while Jacob MacAdam is noted for his capabilities in structuring, establishing and licensing insurance companies. Counsel Dean Bennett specialises in restructurings, schemes of arrangements, and enforcement issues, while Appolina Bent is recommended for regulatory matters.

Regulatory and Compliance

Drawing on close ties with its wider global network of offices, Appleby‘s cross-practice regulatory group is particularly noted for its expertise in privacy, data protection and cybersecurity matters. The team is jointly chaired by global technology and innovation head Peter Colegate; local corporate practice head Simon Raftopoulos, and financial services expert Jacob MacAdam. Senior associate Miriam Smyth is experienced in liaising with financial regulators on information requests, risk mitigation and remediation matters. Counsel Menelik Miller, who joined the team from the Cayman Islands Monetary Authority (CIMA) in March 2022, is also recommended for his far-reaching financial services expertise.

Investment Funds

Drawing on its cross-disciplinary ties with the firm’s technology group, Appleby regularly works on the establishment and structuring of a variety of funds in the digital assets space, particularly in the Asian markets. Practice head Sailaja Alla is highly experienced in the structuring, formation and operation of all manner of fund platforms. Sheila Crosby, who joined the team from Maples Group in October 2021, is recommended for her knowledge of corporate governance and regulatory compliance matters.

Recognised lawyers:

Banking, Finance & Capital Markets:

Corporate & Commercial:

Dispute Resolution:


Investment Funds:

Real Estate

Regulatory and Compliance:

Trusts/Private Client:

The Legal 500 has been analysing the capabilities of law firms across the world, with a comprehensive research programme revised and updated every year to bring the most up-to-date vision of the global legal market. The Legal 500 assesses the strengths of law firms in over 150 jurisdictions highlighting the practice area teams who are providing the most cutting edge and innovative advice.


*Subject to immigration approval

Twitter LinkedIn Email Save as PDF