Stephen Leontsinis

Partner

Legal

Cayman | BVI

+1 345 914 9605 Stephen.Leontsinis@collascrill.com LinkedIn vCard

Stephen has a demonstrated history of advocacy in the practice of corporate and commercial litigation, with an emphasis on offshore insolvency and restructuring of companies. Stephen is qualified in South Africa, England and Wales and Cayman.

Experience

Stephen's practice has a strong focus on company law including corporate insolvency; schemes of arrangements; capital reductions; shareholder disputes; director's liability; international asset tracing; the enforcement of foreign judgments; worldwide Mareva injunctions, Anton Piller orders, and Norwich Pharmacal orders.

Stephen has significant contentious litigation experience arising from the representation of both liquidators, shareholders and creditors of companies and hedge funds including the claw back of fraudulent conveyances and undue preferences, allegations of investment fraud and investment manager disputes.

Since he began heading up our team of Cayman litigators, Stephen has grown the team from two to eight lawyers, all with a strong background in insolvency and restructuring matters. Prior to joining the firm Stephen spent two and a half years in Miami as a member of a boutique litigation firm in the United States which focused on cross border insolvency and trust disputes.

Background

Stephen was called as an advocate of the High Court of South Africa in 2003 and has subsequently qualified as a solicitor-advocate of the High Court of England and Wales and a solicitor-advocate of the Supreme Court of the Eastern Caribbean. He was called to the Cayman Islands Bar in January 2009.

Stephen has been ranked in Chambers and Partners since 2018 and recognised as a Leading Partner in Legal 500 since 2021.

"The Cayman Islands is an extremely sophisticated, competitive jurisdiction and the practice of its laws, whilst challenging, is very rewarding. I am honoured to have grown and led our Cayman Islands Dispute Resolution team since April 2015. We aim to bring a fresh, innovative approach to providing our clients with added value to the normal legal services that they would otherwise expect from any other top tier law firm on the Island."

Clients find Stephen Leontsinis 'client-focused and pragmatic.' Chambers and Partners

Stephen is a fantastic leader of his team, a great advocate for the firm, and an excellent technician. Legal 500 2024

Exceptionally good at seeing the big picture and working strategically to meet necessary goals. Chambers and Partners

Superb – the best litigator in Cayman. Legal 500 2024

Stephen is standout practitioner – drives culture of the firm which is a USP in their way of working collaboratively. Legal 500 2022

Stephen is a phenomenal advocate who is very astute, commercially minded and results-driven. Chambers Global Guide 2022

Stephen is outstanding at stakeholder management and business development. Legal 500 2022

Stephen Leontsinis is a superb litigator and great leader of this growing team, which he has quickly established as a go-to litigation practice. Legal 500

He is an excellent advocate, with a calm and reassuring courtroom manner that resonates well with the Cayman judiciary. Chambers Global Guide 2025

Stephen has an excellent strategic mind. He is a stand-out advocate who is equally effective in the boardroom or behind the scenes. Legal 500 2022

Leading individual. Legal 500

Stephen Leontsinis is a charismatic practice leader and a formidable advocate. His strategic input into restructuring and insolvency engagements is second to none. Chambers Global Guide 2025

Very good and commercial operator with a very personable manner and unique ability to bring opposing sides together. Chambers and Partners

He really understands from a practical perspective what is in the best interests of the client and how all of the pieces of a dispute fit together, often juggling multiple perspectives and viewpoints. Chambers Global 2023

Stephen is highly collaborative, has solid technical skills and never loses sight of the commercial objectives. He is very solution orientated. Legal 500

His knowledge of the Cayman market and all its main players is second to none. Chambers Global Guide 2022

Expertise

In regulatory disputes there are often fine lines between the usual wrangling with the regulator and something more serious – by matching our mix of experienced contentious and non-contentious lawyers to the particular problem at hand, we achieve better and more efficient outcomes.

As regulatory experts in the British Virgin Islands, the Cayman Islands, Guernsey and Jersey we frequently act on contentious matters and can leverage our experience to help clients achieve the highest regulatory standards and avoid common pitfalls.

We combine pragmatic risk assessment with rigorous legal advice and compliance guidance to reduce exposure and protect reputation, while drawing on our cross-jurisdictional knowledge to design remediation strategies, negotiate with regulators and, where necessary, litigate effectively.

Our collaborative approach ensures clients receive clear, actionable legal advice that balances regulatory obligations with commercial realities, delivers timely, proportionate solutions and supports remediation plans, helping prevent escalation into more serious enforcement action and preserve business continuity.

Our dispute resolution specialists collaborate seamlessly with our corporate advisory and banking teams across jurisdictions to advise multinational corporations, trust companies, banks, funds, insurers, governments and directors.

We provide a global perspective, working closely with our clients to ensure that they are best placed to respond to customer issues, fraud risks, rapidly changing market conditions and regulatory demands.

Thanks to the depth of our experience and the resources of our team, we've acted on some of the largest pieces of litigation brought against directors offshore.

We're well placed to deal with the 'bet the farm' proceedings that can occur in these type of disputes and have represented parties involved in intra-company disputes, including executive, non-executive and independent directors, majority and minority shareholders, companies and liquidators. We understand that shareholder disputes are often not black and white and our team finds innovative and commercial alternatives to those which the Court may offer – taking a collaborative approach with our clients to ensure that the right result is achieved.

For financially distressed companies in need of restructuring and reorganisation, or for those where the opportunity to do so has passed or failed, we work to achieve the most beneficial outcome in these difficult situations.

At whatever stage we are engaged, our involvement will assist in identifying the ongoing risks facing a client and to enable that client to continue to identify and effectively manage deteriorating relationships with creditors, financiers, investors or other interested parties.

Arbitration is increasingly being used as a cost-effective, confidential and efficient alternative to court litigation for solving commercial, construction and more frequently trust disputes. The global enforceability of arbitral awards and the successful adoption of virtual technology by most arbitration institutions makes it an attractive option for resolving disputes.

Our dedicated arbitration lawyers bring deep, cross-border experience in both international arbitration and mediation, combining strategic judgment with practical commercial awareness to work alongside and quickly determine the best approach for a successful conclusion. They are skilled at:

Assessing forum suitability
Managing complex stakeholder relationships
Shaping dispute resolution strategies that reflect clients’ broader business objectives

With offices in Bermuda, the British Virgin Islands, the Cayman Islands, Guernsey, Jersey and London as well as a strong track record across a wide range of sectors, our arbitration lawyers can advise you on every aspect of international arbitration, adapting their approach to each dispute while offering clear, commercially rooted guidance aimed at achieving durable, cost-effective outcomes.