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Kirsten  Bailey

Kirsten Bailey 

Associate | Cayman

Dispute Resolution

  • Kirsten Bailey is an extremely good associate.
    Legal 500 2022
  • Kirsten Bailey is exceptionally clever and good with clients.
    Legal 500 (UK) 2023
  • Kirsten Bailey is exceptionally clever and good with clients.
    Legal 500 2023
  • Kirsten Bailey’s work is simply excellent, she has an innate ability to subsume information, process it and produce exceptional product. She definitely has a bright future ahead of her.
    Legal 500 2023
  • Kirsten Bailey’s work is simply excellent, she has an innate ability to subsume information, process it and produce exceptional product. She definitely has a bright future ahead of her.
    Legal 500 (UK) 2023


Kirsten is an Associate and currently on secondment from our Jersey to our Cayman Dispute Resolution department. She advises clients on contentious matters in various areas of law, including contractual disputes, torts and general commercial disputes.

Kirsten also advises on dispute prevention and risk mitigation measures, such as effective contract drafting and negotiation, and alternative dispute resolution mechanisms. She has a particular focus on securing the best solution in the circumstances, whether through litigation or otherwise.


Prior to joining Collas Crill Jersey in October 2019, Kirsten worked at the Johannesburg office of a Pan-African law firm. There, she advised on disputes including class actions, contentious insolvencies, and tax, contract and product liability disputes. She has experience in the Courts of South Africa, Botswana and Tanzania, and her clients included local and international financial institutions, high net worth individuals, major players in the food and beverage sectors and various Johannesburg Stock Exchange-listed entities.

Kirsten has a keen interest in the development of the law in relation to financial technology, especially blockchain and other distributed ledger technology. She advises clients on how fintech can be integrated into dispute resolution mechanisms, and on the resolution of disputes within the sphere.


Kirsten obtained her LLB degree with distinction from the University of Pretoria, South Africa. She is admitted in South Africa, England and Wales and the Cayman Islands.


My services
Contentious Risk and Regulatory

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, we frequently act on contentious matters and can leverage our experience to help clients achieve the highest regulatory standards and avoid common pitfalls. To find out more click here

Contentious Trusts

We represent trust corporations, high net worth individuals, individual trustees and beneficiaries, often dealing with novel points of law and creating new and innovative solutions to fit the needs of our clients. We work as a global team and, given the international scope of settlors, investments and assets, clients benefit from the knowledge and depth of experience of our people around the world.

Director and Shareholder Disputes

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.

Dispute Resolution

When your business is involved in any kind of legal dispute it's crucial to work with lawyers who are hands-on, cost-effective and flexible enough to respond quickly and intuitively to your unique situation and needs. We know that there are many different ways a dispute can be resolved and work closely with our clients to understand every aspect of their business, priorities and goals. This allows us to find the best way forward for our clients and to advise on the commercial implications of a dispute, ensuring the process remains as stress-free as possible. Our approach is practical, responsive and tailored to the client's interests. Our expertise and reputation means we're first choice for a range of clients, including banks, trust companies, high net worth individuals and top law firms.

Insolvency and Restructuring

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. 

Our team brings a wealth of experience from a range of diverse backgrounds to give quick, accurate, commercial advice, primarily across the financial services sector. 

Currently working on some of the largest and most complex cross-border insolvencies in the jurisdiction, we frequently advise top law firms from the People’s Republic of China, the US, the UK and other jurisdictions. We are regularly briefed by Sovereign Wealth Funds and Fortune 500 Companies to advise on particular restructurings, as well as investment managers from Europe and the US.

At whatever stage we are engaged, our involvement will assist in identifying the on-going 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.

News 13 Oct 2022

Collas Crill acts in landmark case

Collas Crill recently acted for the successful lead appellant before the Privy Council in Halabi (Appellant) v Equity Trust (Jersey) Ltd (Respondent) in re the ZII Trusts...

Insight 31 Aug 2022

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A new restructuring regime comes into force today in the Cayman Islands under the Companies (Amendment) Act 2021 (Amendment Act) and the Companies Winding Up (Amendment)...

Insight 30 Aug 2022

Enforcement of judgments - Cayman

The Cayman Islands has long been considered a jurisdiction friendly to foreign investors, not least because of the well-established laws which govern the enforcement of...

Insight 22 Mar 2022

A scheme for one, a scheme for ALL?

In a recent judgment of the English High Court in Re ALL Scheme Limited [2022] EWHC 549 (Ch), Lord Justice Snowden approved a novel approach to schemes of arrangement, by...

Insight 15 Jul 2021

Matter of M Settlement

Case analysis by Group Partner Sam Williams, Of Counsel Fritha Ford and Associate Kirsten Bailey, published on LexisPSL on 8 July 2021 Private Client analysis: The trustee...

Deal 3 Feb 2021

Elementary, my dear Watson

The Royal Court of Jersey has issued a landmark judgment in Kea Investments Limited v Watson [2021] JRC 009, determining that it is not possible to obtain execution measures...

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Event 17 Sep 2020
Past Event

INSOL Virtual 2020

As restructuring professionals are quickly adapting to meeting clients needs under new circumstances INSOL international has decided to present a virtual conference...

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