Rising Stars

Insurance/reinsurance in Cayman Islands


Praised by clients for the depth of knowledge and experience in the market, Campbells‘ cross-practice insurance team acts for a litany of blue-chip clients on the full gamut of contentious and non-contentious matters. The team is jointly chaired by corporate head Alan Craig, a regular adviser to reinsurers and foreign insurers regarding capital market products, and litigator Mark Goodman, whose recent engagements include remediation advisory and regulatory reviews. Paul Kennedy advises a host of clients on matters at the intersections of insurance and corporate insolvency, while ‘superb‘ senior associate Jeremy Durston is noted for his capabilities in regulatory challenges. Associate Kate Hewitson is also recommended.

Practice head(s):

Alan Craig

Other key lawyers:

Paul Kennedy; Mark Goodman; Jeremy Durston; Kate Hewitson


‘Campbells insurance team is one of the most knowledgeable firms for life insurers in the Cayman Islands. They have a vast amount of experience in the insurance business and are key players in the insurance regulatory market.’

‘Alan Craig leads with an enormous amount of experience in the insurance space and creates dialogue among his clients to provide practical solutions to issues facing regulatory and international challenges.’

‘Jeremy Durston is superb. His understanding and guidance through processes stand out as one of the best. I have appreciated the promptness this firm gives to their clients as well as a practical approach to implementing procedures that make common sense.’

‘Alan Craig is very responsive and is always willing to help.’

Key clients

Next Era Energy

Prosperity Life

Argus / Bermuda Life

Advantage Insurance

Western International



Willis Towers Watson

Cooper Gay / Ed Broking

Island Heritage

ICWI (Insurance Company of the West Indies)

Guardian Life

Global Captive Management

Artex Risk Solutions

Caribbean Catastrophe Risk Insurance Facility

Guardian Insurance

Strategic Risk Solutions

Beecher Carlson

Crum & Forster

Cottingham & Butler

United Health Group

Innovative Captive Strategies

Caribbean Alliance

Pan-American Life

Investors Trust

Work highlights

  • Advising NextEra Energy with respect to its Cayman captive insurance subsidiary.
  • Acting as counsel to Pan-American Life with respect to Cayman insurance matters.
  • Working with UnitedHealth Group on insurance structuring matters.


Conyers draws superlative praise from a myriad of high-profile clients for the ‘quality of service and professionalism‘ of its dedicated (re)insurance practice. Steered by Derek Stenson – ‘a highly respected lawyer who consistently delivers results above and beyond expectations‘ – the team is consistently engaged on a mix of big-ticket transactions, disputes, regulatory reviews and investigative actions. Senior associate Philippa Gilkes is praised by clients for her ‘fantastic industry knowledge and expertise’, ranging from handling the establishment and licensing of new companies to multi-billion-dollar reinsurance transactions. Associate Sarah Farquhar is also recommended for regulatory and compliance matters. Counsel Rob Humphries left the practice in April 2022.

Practice head(s):

Derek Stenson

Other key lawyers:

Philippa Gilkes; Sarah Farquhar


‘Philippa Gilkes is incredibly responsive. I’m always confident clients are in good hands when working with her.’

‘All-round superb offering with unmatched on-shore and offshore knowledge and hands-on expertise. There is no other insurance/reinsurance team on island that matches them in terms of the quality of service, quick turnaround and the professionalism that they deliver, time and time again on each and every assignment.’

‘Derek Stenson is an extremely attentive, knowledgeable, diligent, and highly respected lawyer who consistently delivers results above and beyond expectations.’

‘Philippa Gilkes is a highly competent lawyer with fantastic industry knowledge and expertise.’

‘Sarah Farquhar is highly competent with a proven, well-deserved track record of excellence and an impressive work ethic.’

‘Derek Stenson and his team are an asset to the industry. They are quick to respond and are very knowledgeable.’

Key clients



Aran Re


Athene Holding Ltd.

Ascension Health

Assurant Inc.

Aran Re

Axar Re

Baptist Health

Barents Re


Berkshire Hathaway

BOLT Reinsurance SPC

Boston Medical Center Insurance Company, Ltd.

CIBC Reinsurance


Comerica Bank

Crestline Re


Global Atlantic Financial Group

Heritage Life Insurance Company

Island Heritage Insurance Company, Ltd.

Jackson National


Knighthead Annuity

Liberty Mutual

Longtail Re


Prudential plc

Nirvana Tech, Inc,

Randall & Quilter Investment Holdings Ltd.

Root Inc.

Royal Bank of Canada Insurance Company Limited

Sixth Street


Tokio Marine

Topsail Re

United Insurance Company

Work highlights

  • Acted for Sixth Street on the establishment and licensing of Talcott Life & Annuity Re, Ltd. and provided legal and regulatory advice in respect of its entry into of a reinsurance transaction with Principal Financial Group pursuant to which it reinsured approximately $25bn of liabilities.
  • Acted as Cayman Islands counsel with regards to the establishment of Ivy Co-Investment Vehicle II LLC, designed to co-invest approximately $1bn with Global Atlantic and its subsidiaries in qualifying reinsurance transactions.
  • Advising a member of Augusta Healthcare, Inc. in relation to a quasi-partnership dispute involving a captive insurance company incorporated in the Cayman Islands to provide insurance solutions for not-for-profit healthcare systems.


Walkers is reputed for the depth of its expertise in regulatory insurance matters, handling a mix of licensee applications, share deals and restructurings, as well as senior management training initiatives and CIMA remediation compliance reviews. Joint practice chairs Philip Paschalides and Tony De Quintal – who was promoted to partner in July 2021 – are noted for their expertise in big-ticket reinsurance transactions. Global risk and regulatory head Lucy Frew advises various insurers and reinsurers on a host of compliance matters, ranging from insurtech investment opportunities to anti-money laundering obligations. Senior counsel Juliana Tang is well-versed in both cross-border transactions and regulatory reviews. Associate Sarah Dombowsky is also noted.

Practice head(s):

Tony De Quintal; Philip Paschalides

Other key lawyers:

Sarah Dombowsky; Lucy Frew; Juliana Tang


‘Combine regulatory and structured finance expertise in an extremely commercial manner.’

‘Philip Paschalides has provided world class structured finance advice.’

‘The team is very responsive and engaging. They have a wealth of knowledge and a broad network of expertise to draw from. Walkers is a go-to firm for anyone in the industry.’

‘Tony De Quintal is a straight shooter. He will tell you like it is without all the fluff. He is always ready to help and open to out-of-the-box thinking.’


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. Senior associate Dean Bennett specialises in restructurings, schemes of arrangements, and enforcement issues, while Appolina Bent is recommended for regulatory matters.

Practice head(s):

Simon Raftopoulos

Other key lawyers:

Jacob MacAdam; Appolina Bent; Dean Bennett


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

‘Jacob MacAdam provides consistently sound advice on complicated matters.’

Key clients

Brookfield Asset Management Inc.

Brickell Insurance Holdings LLC

Kuvare Life Re Ltd.

Work highlights

  • Acted as Cayman counsel to Brookfield Asset Management in connection with the incorporation of a Cayman Islands exempted company as a regulated reinsurance vehicle, the licensing of the reinsurer with the Cayman Islands Monetary Authority (CIMA), and the conversion of the reinsurer into a segregated portfolio company.
  • Acted as Cayman Islands legal counsel to Brickell Insurance Holdings PC LLC.

Maples Group

Maples Group‘s cross-disciplinary insurance practice is sought out by a number of public and private sector clients for assistance with the full range of transactional and general advisory matters. Tim Frawley regularly handles a diverse array of work, including new company formations, regulatory reviews, and insurance-linked securities. Abraham Thoppil is noted for his expertise in insurtech and insurance legislation, while John Dykstra is well regarded on account of his active catastrophe bond transaction practice.

Practice head(s):

Tim Frawley

Other key lawyers:

Abraham Thoppil; John Dykstra

Key clients

United Insurance Company,

Signature Insurance Company

United SPC

Cayman First Insurance Company Limited

Oxbridge Reinsurance Limited

Knighthead Annuity & Life Assurance Company

Nassau Re (Cayman) Ltd.

Island Heritage Insurance Company, Ltd.

Brac Insurance Associates Ltd.

Magni Re Ltd.

Cayman Islands Government

Work highlights

  • Advised BlackRock in connection with the $300m senior term loan made to Root Inc. by Blackrock, its affiliates and co-investors.
  • Providing ongoing legal advice to Oxbridge.
  • Providing ongoing legal advice to Knighthead.