Appleby has been praised for having “a team of talented lawyers dedicated to their work and to high quality performance” in the 2025 edition of The Legal 500 Caribbean, with the Group achieving nine Tier 1 rankings across the region. In addition, more than 40 of the Group’s Bermuda, British Virgin Islands (BVI) and Cayman Islands lawyers have either been ranked or individually recognised within the directory, including 18 as ‘Leading Partners’.
In Bermuda, Appleby remains the highest-ranking law firm and the only one to achieve Tier 1 rankings across all six available practice area categories – Banking, Finance & Capital Markets; Corporate & Commercial; Dispute Resolution; Insurance/Reinsurance; Regulatory & Compliance; and Trusts/Private Client.
Similarly, the Cayman Islands office has continued to secure Tier 1 rankings for Banking, Finance and Capital Markets; Real Estate; and Trusts/Private Client.
Together with the Group’s rankings for the BVI, which include Tier 2 rankings for both Corporate & Commercial; and Dispute Resolution, Appleby is ranked for 18 practice areas across the Caribbean region.
Further commentary and feedback in this year’s guide includes Appleby’s Insurance practice in Bermuda being described as “phenomenal” and praised for its “great insurance industry and regulatory landscape knowledge”. Similarly, the Bermuda Dispute Resolution team is “very well resourced and with many of the best lawyers on the island”, while another industry source highlighted how the team’s “experience and competence in dispute resolution matters related to our industry are unmatched in Bermuda”. The Banking, Finance and Capital Markets team has “excellent technical skills” and is noted for providing “highly responsive, commercial and thoughtful advice”.
For the Cayman Islands, the Banking, Finance and Capital Markets team is recognised as “one of the go-to firms in fund financing, as well as offering a broad and strong service across structured finance, corporate finance, and the range of adjacent practice areas”. The Real Estate practice is noted for possessing a “team of outstanding attorneys and veteran paralegals which is not matched by any other team in the Cayman Islands”, while the Private Client & Trusts practice is considered “the right blend of commercial expertise blended with technical expertise that makes them the perfect private client team”. From a Dispute Resolution perspective, the Cayman office also has “a top-class team very experienced in high value offshore litigation”.
In the BVI, the office’s Dispute Resolution team is recognised as “a top-notch practice, deeply expert in local practice and very capable across the board” as well as for being able to handle “multiple big cases and being valuable members of big cross-border teams of advisers”. Similarly, the Regulatory team is considered “our go-to firm in the Caribbean for compliance and corporate issues” by one industry commentator, while another highlighted how the team is “thoughtful and creative in evaluating regulatory questions for digital asset industry business models for which there is limited direct precedent”.
The Group’s individual rankings are as follows:
LEADING PARTNERS
Bermuda
- Managing Partner Brad Adderley (Insurance/Reinsurance; Corporate and Commercial)
- Partner David Clark (Banking, Finance and Capital Markets)
- Partner Matthew Ebbs-Brewer (Corporate and Commercial)
- Partner Clive Langley (Banking, Finance and Capital Markets)
- Partner Sally Penrose (Regulatory and Compliance)
- Partner Tammy Richardson-Augustus (Banking, Finance and Capital Markets)
- Partner John Wasty (Dispute Resolution; Regulatory and Compliance)
- Partner Jerome Wilson (Corporate and Commercial)
- Senior Counsel Vanessa Schrum (Trusts/Private Client)
BVI
- Managing Partner Jeffrey Kirk (Corporate and Commercial)
- Partner Andrew Willins (Dispute Resolution)
Cayman Islands
- Managing Partner Norman Klein (Real Estate)
- Partner Caroline Barton (Banking, Finance and Capital Markets)
- Partner Adam Johnson (Real Estate)
- Partner Simon Raftopoulos (Banking, Finance and Capital Markets)
- Partner Sebastian Said (Dispute Resolution)
- Partner Carlos de Serpa Pimentel (Trusts/Private Client)
- Partner Benjamin Woolf (Banking, Finance and Capital Markets)
NEXT GENERATION PARTNERS
BERMUDA
- Partner Matthew Carr (Insurance/Reinsurance)
- Partner Sam Riihiluoma (Dispute Resolution; Trusts/Private Client)
BVI
- Partner Shana Simmonds (Corporate and Commercial)
Cayman Islands
- Partner Dean Bennett (Corporate and Commercial)
- Partner Peter Colegate (Regulatory and Compliance)
- Partner Georgina Pullinger (Banking, Finance and Capital Markets)
LEADING ASSOCIATES
BERMUDA
- Counsel James Batten (Dispute Resolution)
- Counsel Josephine Noddings (Corporate and Commercial; Insurance/Reinsurance)
- Counsel Caljonah Smith (Trusts/Private Client)
- Associate Arielle DeSilva (Banking, Finance and Capital Markets)
Cayman Islands
- Counsel Esmond Brown (Trusts/Private Client)
- Senior Associate Tim Swallow (Real Estate)
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Further recommendations in this year’s directory where individuals have been recognised as ‘Other key lawyers’ within a particular practice area are as follows:
BERMUDA
Managing Partner Brad Adderley (Banking, Finance and Capital Markets), Partner Nicola Bruce (Trusts/Private Client), Partner David Clark (Corporate and Commercial), Partner Clive Langley (Corporate and Commercial), Partner John Wasty (Insurance and Reinsurance), Partner Jerome Wilson (Banking, Finance and Capital Markets), Counsel Khiyara Krige (Dispute Resolution), Counsel Cathryn Minors (Insurance and Reinsurance) and Senior Associate Carl Meyer (Corporate and Commercial)
BVI
Managing Partner Jeffrey Kirk (Banking, Finance and Capital Markets; Regulatory and Compliance), Partner Olwyn Barry (Dispute Resolution), Partner David Clark (Banking, Finance and Capital Markets; Corporate and Commercial; Regulatory and Compliance), Partner Andrew Jowett (Banking, Finance and Capital Markets; Corporate and Commercial; Regulatory and Compliance), Partner Daniel Mitchell (Dispute Resolution), Partner Shana Simmonds (Banking, Finance and Capital Markets), Counsel Tamara Cameron (Dispute Resolution), Counsel Brittany Cummings (Corporate and Commercial) and Senior Associate Laure-Astrid Wigglesworth (Dispute Resolution)
Cayman Islands
Partner Sailaja Alla (Investment Funds), Partner Jacob MacAdam (Corporate and Commercial; Insurance/Reinsurance), Partner Matt Mulry (Investment Funds), Partner Simon Raftopoulos (Corporate and Commercial; Insurance/Reinsurance), Partner Sebastian Said (Trusts/Private Client), Partner Benjamin Woolf (Corporate and Commercial), Counsel Menelik Miller (Insurance/Reinsurance; Regulatory and Compliance), Counsel Miriam Smyth (Insurance/Reinsurance), Senior Associate Alexandra Low (Corporate and Commercial; Investment Funds), Senior Associate Vance Power (Corporate and Commercial) and Associate Jackson Messer (Trusts/Private Client)
A leading directory for the legal directory, The Legal 500 ranks law firms and their lawyers following a thorough and independent research process which includes feedback from 300,000 clients, private practice lawyers and in-house peers as well as the assessment of a law firm’s own deals and confidential matters.
