Katharine Bailey has a busy and varied practice spanning Chambers’ core practice areas, with particular focus on commercial and insolvency, constitutional and administrative law (including appeals to the Privy Council), employment, and travel (including aviation).

Katharine is recognised in the Legal 500 as a Rising Star (Tier 1) ‘The English Bar (Offshore)’, which describes her as “extremely clear”, “incredibly bright”, and willing to “go above and beyond to respond to any queries put to her”.

Katharine is instructed as sole counsel in trials and interlocutory hearings, and has also acted as part of counsel teams in the High Court, Court of Appeal, and Privy Council. Katharine’s recent experience includes:

  • Matrix Receivables Limited v Musst Holdings Limited (on-going) – as junior counsel for Musst (led by Peter Knox KC). This is a financial services sector dispute in the Business & Property Courts (Business List); Matrix claim for a share (in contract or quantum meruit) of Musst’s management and performance fees derived from managed funds which follow a specific investment strategy (to invest primarily in synthetic asset-backed securities). This litigation is linked to the on-going dispute between Musst Holdings Ltd v Astra Asset Management UK Ltd (see below).
  • Musst Holdings v Astra Asset Management UK Ltd (on-going) – as junior counsel for Musst (led by Peter Knox KC). This is another financial services sector dispute which arises out of a three-week trial before Mr Justice Freedman in 2021 ([2021] EWHC 3432 (Ch)). Musst claims it is entitled to management/performance fees arising from further funds managed by Astra which follow a specific investment strategy. Peter and Katharine successfully resisted Astra’s application for strike out of and/or summary judgment on this claim ([2023] EWHC 432 (Ch); [2023] 2 WLUK 448). Peter and Katharine also acted for Musst in the Court of Appeal (successfully resisting Astra’s appeal) ([2023] EWCA Civ 128; [2023] 2 WLUK 191).
  • Chong & Ors v Financial Services Compensation Scheme Limited [2024] EWHC 3374 (Admin) – acting (with Rowan Pennington-Benton) in a challenge by judicial review to a decision of the Financial Services Compensation Scheme Limited in the context of offering compensation to applicants with potential claims against SIPP operators pursuant to section 27 of the Financial Services and Markets Act 2000 in light of the decision of the Court of Appeal in Adams v Options UK Personal Pensions LLP [2021] EWCA Civ 474
  • Ervin Dean v Bahamas Power & Light [2024] UKPC 20 – acting (led by Dywan Rogers, Meridian Law Chambers (The Bahamas)) for BPL the government corporation providing electricity to all of the Bahama Islands, except Grand Bahama) in an appeal to the Privy Council concerning the scope of the principle of ‘unjust dismissal’ (contractual and/or common law), as distinct from statutory ‘unfair dismissal’, in the context of an Industrial Agreement between BPL and its workforce.
  • Dhoray v Attorney General of Trinidad and Tobago [2024] UKPC 28 – acting (led by Anand Ramlogan SC, Freedom Law Chambers (Trinidad & Tobago) and Robert Strang in this significant challenge to the constitutionality of primary legislation: the Trinidad and Tobago Revenue Authority Act, Act. No. 17 of 2021, pursuant to which the Government introduced new body corporate, the Trinidad and Tobago Revenue Authority, which would assume responsibility for tax assessment and collection. This decision contains an important ruling on the rationale for Chapter 9 of the Constitution, vesting in the Public Service Commission the power of appointment and removal over officers employed in the service of the government. 
  • Innovate Pharmaceuticals Limited v University of Portsmouth Education Corporation [2023] EWHC 35 (TCC) – as junior counsel (led by Thomas Roe KC, Deputy Head of Chambers). This was a four-week trial in the Technology & Construction Court in which Thomas and Katharine acted on behalf of Innovate who succeeded in their claim for breach of contract against the University of Portsmouth. The dispute arose from a contract to evaluate the efficacy of a new drug and involved complex patent value and pharmacology expert evidence.

Expertise

Katharine is developing a broad practice encompassing all aspects of commercial, company and insolvency litigation and advisory work. She is currently instructed on cases concerning civil fraud, breach of director duties, and complex contractual disputes. Much of Katharine’s caseload has an international element giving rise to jurisdiction challenges, cross-border recognition, and enforcement considerations. In addition, Katharine is instructed on cases involving complex expert evidence.

Katharine also has a busy advocacy and advisory commercial practice as sole counsel, acting on behalf of both individuals and businesses. Recently, Katharine acted as sole counsel in a three-day commercial trial in the Central London County Court (Business & Property List), during which Katharine cross-examined three factual witnesses. Katharine’s client succeeded on the contract claim and recovered costs on the indemnity basis.

Katharine also regularly deals with company and insolvency matters as sole counsel. She is instructed to appear in winding up and bankruptcy petitions on a regular basis, and she has recent experience advising office-holders in connection with potential claims against company officers involving breach of fiduciary/statutory duty, misfeasance, and antecedent transactions.

Notable Commercial, Company & Insolvency cases

GR123

Katharine (led by Daniel Feetham KC (Gibraltar)) is currently instructed as junior counsel (alongside Rowan Pennington-Benton and Thomas Horton), in litigation arising out of the collapse of GR123 (formerly MCE Insurance Ltd), a UK/Gibraltar motor insurance underwriter. This case involves complex forensic accountancy and actuarial expert evidence. Katharine has been heavily involved in the preparation of the claim, and more recently the application to the Gibraltar Supreme Court for permission to serve out.

Matrix Receivables Limited v Musst Holdings Limited

Katharine is led by Peter Knox KC in this financial services sector dispute. Matrix claim for a share (in contract or quantum meruit) of Musst’s management and performance fees derived from managed funds which follow a specific investment strategy (to invest primarily in synthetic asset-backed securities). In May 2024, Peter and Katharine argued Musst’s application for reverse summary judgment on, and/or strike out of, Matrix’s claim, which was heard over two days in the Business & Property Courts (Business List) before Mr Justice Freedman. This litigation is linked to the on-going dispute between Musst Holdings Ltd v Astra Asset Management UK Ltd (see below).

Innovate Pharmaceuticals Limited v University of Portsmouth Education Corporation [2023] EWHC 35 (TCC)

Katharine, led by Thomas Roe KC (Deputy Head of Chambers), acted on behalf of Innovate who succeeded in their claim for breach of contract against the University of Portsmouth. The dispute arose from a contract to evaluate the efficacy of a new drug and involved complex patent value and pharmacology expert evidence.

Musst Holdings Ltd v Astra Asset Management UK Ltd

Katharine is led by Peter Knox KC in this dispute, which arises out of the three-week trial before Mr Justice Freedman in 2021 ([2021] EWHC 3432 (Ch)). Musst claims it is entitled to management/performance fees arising from further funds managed by Astra which follow the same specific investment strategy. Recently, Musst successfully resisted Astra’s application for strike out and/or summary judgment ([2023] EWHC 432 (Ch); [2023] 2 WLUK 448).

Musst Holdings Ltd v Astra Asset Management UK Ltd [2023] EWCA Civ 128; [2023] 2 WLUK 191

Katharine, led by Peter Knox KC, acted for Musst, who succeeded in the Court of Appeal in upholding the decision of Mr Justice Freedman.

Innovate Pharmaceuticals Limited v University of Portsmouth Higher Education Corporation [2022] EWHC 1681 (TCC)

Katharine, led by Thomas Roe KC, successfully resisted an application for security for costs on the unusual ground of the merits of the claim as demonstrable on a summary basis.

Katharine’s offshore practice includes regular appearances as junior counsel in appeals to the Judicial Committee of the Privy Council from the Caribbean. Katharine acts for governments, businesses and individuals and has appeared in appeals from The Bahamas, Trinidad and Tobago, and St. Lucia. Katharine has a busy offshore advisory practice and has been instructed in the last year on disputes arising out of Singapore, The Bahamas, Trinidad and Tobago, and Gibraltar.

Katharine is also currently instructed as junior counsel in a complex, large-scale cross-border insolvency matter involving a Gibraltar-based insurance company. Katharine is led by Daniel Feetham KC (Gibraltar) alongside several other juniors in Chambers as part of the UK-based legal team working closely with Gibraltar-based lawyers and recovery professionals in investigatory and advisory work concerning the collapse of GR123 (formerly MCE Insurance Ltd), a UK/Gibraltar motor insurance underwriter.

Notable Appeals to the Privy Council / Offshore cases

Sobers & Joseph v Attorney General of Trinidad and Tobago

Junior counsel, led by Rowan Pennington-Benton, in this appeal concerning whether the Court of Appeal of Trinidad & Tobago erred in setting aside a test case agreement and consent order. The appeal involved statutory construction of section 39 of the Supreme Court of Judicature Act (Chapter 4:01) (a less-than-straightforward piece of legislation considered by the Board almost exactly one year earlier in Caribbean Welding Supplies Ltd v Attorney General of Trinidad and Tobago [2024] UKPC 7).

Ervin Dean v Bahamas Power & Light Company Ltd [2024] UKPC 20

Junior counsel, led by Dywan Rodgers (Meridian Law Chambers, The Bahamas). Dywan and Katharine acted for BPL Ltd (the government corporation providing electricity to all of the Bahama Islands, except Grand Bahama). The principal issue was the scope of the principle (contractual and/or common law) of ‘unjust dismissal’, as distinct from statutory ‘unfair dismissal’, in the context of an Industrial Agreement between BPL Ltd and its workforce.

Charles Edward Porter & Anr v Robert Stokes [2023] UKPC 11; [2023] 3 WLUK 519

Led by Robert Strang and Trinidad Senior Counsel in March 2023 in a private law appeal from Trinidad and Tobago concerning a disputed conveyance of land.

Anthony Henry & Anr v Attorney General of St Lucia [2023] UKPC 41; [2023] 11 WLUK 449

Led by Robert Strang and Trinidad Senior Counsel in a constitutional appeal from St. Lucia concerning the right to personal liberty and protection from inhuman and degrading treatment (the Board’s decision also contains helpful guidance on implied repeal and quantification of vindicatory damages).

Attorney General of Trinidad and Tobago v JM (A minor by his kin and Next Friend NM) [2022] UKPC 54; [2022] 12 WLUK 273

Led by Howard Stevens KC (Head of Chambers) in October 2022 in an appeal from Trinidad and Tobago concerning the scope of constitutional vindicatory damages.

Duncan and Jokhan v Attorney General of Trinidad and Tobago [2021] UKPC 17; [2021] 7 WLUK 140

Katharine (as a pupil) assisted Tom Poole KC in drafting the Respondent’s Written Case in an appeal concerning whether there was a violation of the Appellants’ rights under section 4(a) of the Constitution not to be deprived of liberty and security of the person except by due process of law.

Betaudier v Attorney General of Trinidad and Tobago [2021] UKPC 7; [2021] 3 WLUK 502

Katharine (as a pupil) assisted Tom Poole KC in drafting the Respondent’s Written Case in an appeal concerning the lawfulness of the Appellant’s arrest and subsequent detention.

Katharine is a member of the Attorney General’s Junior Junior Scheme. She is particularly interested in public and constitutional law.

Katharine is instructed as Junior Counsel to the Iraq Fatality Investigations, established following R (Ali Mousa and others) v Secretary of State for Defence [2013] EWHC 1412 (Admin) in order to meet the state’s obligations under Article 2 of the ECHR. Katharine’s role involves assisting the current Inspector, Dame Anne Rafferty, with her investigations into the deaths of Radhi Nama and Mousa Ali (two detained civilians who deaths involve allegations of ill treatment at a British army base near Basrah in May 2003) and Ahmed Jabbar Kareem Ali (an investigation concerned with identifying whether there was a systemic practice of ‘wetting’ as a law-enforcement mechanism in the post-war phase of British Occupation in 2003). The Iraq Fatality Investigations held public hearings on 11, 12 and 13 April 2023, and 7 August 2023, during which. Katharine posed questions, on behalf of the Inspector, to a military witness to the death of Radhi Nama.

Through the Attorney General’s Junior Scheme, Katharine has worked on Phase 5 of the Post Office Horizon Inquiry (which addresses, amongst other things, access to justice, responding to the scandal and compensation schemes). Katharine assisted the Counsel to the Inquiry Team by reviewing relevant documentation and preparing questions for the cross-examination of witnesses.

Katharine is also interested in constitutional law, and is regularly instructed as junior counsel in appellate work before the Judicial Committee of the Privy Council, working in particular on disputes arising out of the Commonwealth Caribbean.

Notable Public, Constitutional Law & Inquiries cases

Chong & Ors v Financial Services Compensation Scheme Limited [2024] EWHC 3374 (Admin)

Acting with Rowan Pennington-Benton in a challenge by judicial review to a decision of the Financial Services Compensation Scheme Limited in the context of offering compensation to applicants with potential claims against SIPP operators pursuant to section 27 of the Financial Services and Markets Act 2000 in light of the decision of the Court of Appeal in Adams v Options UK Personal Pensions LLP [2021] EWCA Civ 474.

Dhoray v Attorney General of Trinidad and Tobago [2024] UKPC 28

acting (led by Anand Ramlogan SC, Freedom Law Chambers (Trinidad & Tobago) and Robert Strang in this significant challenge to the constitutionality of primary legislation: the Trinidad and Tobago Revenue Authority Act, Act. No. 17 of 2021, pursuant to which the Government introduced new body corporate, the Trinidad and Tobago Revenue Authority, which would assume responsibility for tax assessment and collection. This decision contains an important ruling on the rationale for Chapter 9 of the Constitution, vesting in the Public Service Commission the power of appointment and removal over officers employed in the service of the government. Robert and Katharine wrote a detailed analysis for LexisNexis on this appeal, which can be accessed above.

Iraq Fatality Investigations

Katharine’s role in the current investigations has included analysis of evidence, preparation for and conducting cross-examination of military witnesses, and assisting the Inspector, Dame Anne Rafferty, with report writing.

Attorney General of Trinidad and Tobago v JM (A minor by his kin and Next Friend NM) [2022] UKPC 54

Led by Howard Stevens KC (Head of Chambers) in October 2022 in an appeal from Trinidad and Tobago concerning the scope of constitutional vindicatory damages.

Anthony Henry & Anr v Attorney General of St Lucia [2023] UKPC 41

Led by Robert Strang and Trinidad Senior Counsel in a constitutional appeal from St. Lucia concerning the right to personal liberty and protection from inhuman and degrading treatment (the Board’s decision also contains helpful guidance on implied repeal and quantification of vindicatory damages).

Duncan and Jokhan v Attorney General of Trinidad and Tobago [2021] UKPC 17

Katharine (as a pupil) assisted Tom Poole KC in drafting the Respondent’s Written Case in an appeal concerning whether there was a violation of the Appellants’ rights under section 4(a) of the Constitution not to be deprived of liberty and security of the person except by due process of law.

Betaudier v Attorney General of Trinidad and Tobago [2021] UKPC 7

Katharine (as a pupil) assisted Tom Poole KC in drafting the Respondent’s Written Case in an appeal concerning the lawfulness of the Appellant’s arrest and subsequent detention.

Katharine (as a pupil) assisted Thomas Roe KC in preparing the Respondent’s Written Case for an appeal concerning apparent bias and the scope of the protection afforded by sections 4(a) and 5(2)(f)(ii) of the Constitution.

Katharine has considerable experience advising on employment law. She worked as a Consultant to Withers LLP between September 2021 and March 2022, where she was involved in matters concerning breach of contract (including post-termination restrictions), bonus and other contractual disputes, unfair and constructive unfair dismissal, partnership and shareholder disputes, whistleblowing, and discrimination. Prior to commencing pupillage, she worked for over a year as a paralegal with the employment team at Withers LLP.

Katharine appears regularly in the Employment Tribunal in preliminary and final hearings across a range of claims. Katharine has dealt with claims concerning unfair dismissal, discrimination, TUPE, and unlawful deduction of wages. Katharine also has experience of judicial mediation and negotiations. Katharine acts for both employers and employees and is particularly well-placed to advise on employment claims litigated in the civil courts, including breach of contract claims and those where there is a potential personal injury and/or common law negligence component.

Katharine also brings her employment/labour law expertise to bear on her Privy Council practice. Recently, she was led by Dywan Rodgers (Meridian Law Chambers, The Bahamas) in Ervin Dean v Bahamas Power & Light Company Limited, an appeal to the Board in which the principal issue was the scope of the principle of ‘unjust dismissal’, as distinct from statutory ‘unfair dismissal’, as a matter of Bahamian law in the context of an Industrial Agreement between BPL and its workforce.

During pupillage, Katharine assisted Tom Poole KC in a 10-day Employment Tribunal hearing involving allegations of sexual harassment, victimisation and unfair dismissal; she also assisted Tom in connection with advisory work addressing unlawful deduction from wages and the enforceability of restrictive covenants. Under supervision, Katharine assisted on a variety of complex employment matters, which often raised discrimination and data protection considerations. Katharine co-wrote an article for the International Employment Lawyer on how employers can prepare for an emerging AI regulatory landscape and recently delivered a presentation to the Equality and Human Rights Commission’s enforcement team on artificial intelligence and algorithmic bias in the employment context.

Katharine is instructed in a range of property matters (both residential and commercial), including claims for interim and final injunctive relief and Part 8 claims. She has appeared in the High Court (unled) defending a complex, multi-party urgent application for injunctive relief arising out of allegations of nuisance, trespass and harassment. In February 2025, she acted (as sole counsel) for the respondent to an urgent application for interim injunctive relief arising out of a possession dispute involving allegations of unlawful eviction, harassment and trespass. Katharine secured the dismissal of the application with costs. Katharine is regularly instructed to advise and act in possession claims (including claims against trespassers), business tenancy disputes and disputes concerning trusts of land and co-ownership. She also has a busy paperwork practice in these areas.

During pupillage, Katharine assisted Tom Poole KC in the legally significant Privy Council case of Gordon v Havener (Antigua and Barbuda) [2021] UKPC 26, in which Lord Burrows clarified the law of proprietary estoppel as it relates to contract-breakers.

Katharine is regularly instructed in matters involving the Package Travel Regulations, the Montreal Convention, and the Athens Convention. Katharine’s caseload covers trials, interim applications, and costs and case management conferences. Katharine also represents various airlines in passenger claims for compensation under the EU Denied Boarding Regulations (EC Regulation 261/2004). She also has experience of CEDR adjudication work. She also maintains a busy paperwork practice in this area, drafting advices (eg. on jurisdictional and procedural points, local standards/expert evidence, or quantum), pleadings, and schedules of loss.

Katharine is developing her aviation practice alongside her busy and varied travel law practice. Her aviation work includes drafting, advisory, and advocacy work in matters such as:

  • Carriage by air disputes involving EU regulations, Warsaw and Montreal Conventions and associated passenger, cargo, baggage, delay and denied boarding claims.
  • Travel claims, including under the Package Travel Regulations, particularly representing airlines in “mixed liability scheme” claims.

Katharine is instructed in a range of (non-clinical) professional negligence cases, especially against legal practitioners and property professionals. She has a busy advisory practice in this area.

Notable Professional Negligence cases

Acting (led by Tom Poole KC) in a claim against solicitors for alleged misconduct of an investment treaty arbitration.

Advising in a claim against architects for providing negligent advice on the scope and content of an application for planning permission, and for failing to advise adequately on costs and fees.

Advising in a claim against surveyors where the client suffered significant loss flowing from inaccurate advice on the demarcation of boundaries.

Advising (as junior counsel) in a claim for damages for misconduct of litigation/settlement at an undervalue of a high-value equal pay claim.

‘Katharine is extremely clear and familiar with principles and case law when being instructed on any given matter and would go above and beyond to respond to any queries put forward to her. She is incredibly bright and her drafting skills are excellent, she thinks about all possible angles in a case, and she is also responsive and communicates well so expectations are aligned.’ - Caribbean - The English Bar Offshore - Other expertise (Rising Star)

Legal 500 2025

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