Kirsten  Bailey

Kirsten Bailey 

Associate | Cayman

Insolvency and Corporate Disputes

  • Kirsten is fantastic to work with. She grasps technical matters easily, works effortlessly and is a great associate.
  • 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’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 in the Insolvency and Corporate Disputes team and currently on secondment in our Cayman office. 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
Corporate disputes

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.


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.

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.

29 Feb 2024

AI: The benefits and risks in legal practice

This article first appeared in TL4 FIRE Starters | Essay Competition issue in February 2024  “Of all the dystopian futures I considered, one where machines make the art and humans do the hard labour is not the one I wanted”. This sentiment and ones ...

1 Dec 2023

St Ignatius wins the Cayman Collas Crill Moot

Soleya Manzanares and Leanna Allen of St Ignatius Catholic School have won the Cayman Collas Crill Moot. Cayman Prep High School's Asia Carter and Reuben Strand came second, Abriann and Daniel Cooper from Cayman International School took third and Clifto...

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 2022 UKPC 36, in a case that will undoubtedly have a far-reaching and long-lasting ...

31 Aug 2022

A new era of restructuring - Cayman

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) Rules 2022 (Amendment Rules), referred to herein as the Restructuring Regime. As...

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 foreign judgments and arbitration awards. In the Cayman Islands chapter of the Chambe...

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 which creditors will be given the opportunity to vote on two alternate schemes at a...

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