Winston Jacob

Winston specialises in property, commercial and insolvency litigation. He provides advice, drafting and advocacy to clients across these specialisms. Please click on a specialism link below for more details of his experience in the relevant practice area.

He has appeared as sole counsel at all levels up to the Court of Appeal and has drafted a notice of objection to permission to appeal in the Supreme Court. He regularly appears in the High Court, the County Court, the First-tier Tribunal and the Upper Tribunal in petitions, applications and trials. He appeared in the Court of Appeal for the successful Appellant in Elim Court RTM Co Ltd v Avon Freeholds Ltd [2017] H.L.R. 18; [2017] EWCA Civ 89.

He has particular experience of commercial debt recovery, personal insolvency, mortgage disputes and landlord and tenant.

Winston prosecutes for the BSB before the Bar Disciplinary Tribunal. He has also taken part in the Chancery Bar’s pro bono CLIPS scheme to assist litigants in person in the High Court.

He has provided insolvency training to the internal lawyers at the Bar Standards Board. He has provided lectures on various topics to solicitors, corporate lay clients and the judiciary.

Winston edits the Tenant arrears and bankruptcy section of the RICS isurv website.

In certain circumstances, Winston accepts direct instructions on a public access basis.

Winston was appointed a Deputy District Judge on the South Eastern Circuit in May 2020.


“Thank you for your help in this multi track trial. The outcome was an unconditional victory, and the clients were very impressed with your performance. As they put it: ‘we believe you all could not have fought harder for us and we certainly couldn’t have wanted for any more. Winston was outstanding. He ran rings around the opposition.'”: John Gordon, Partner, Wilson Browne Solicitors

“I recently instructed Winston in a complex property damage and boundary case. He provided invaluable advice throughout the process; in particular, on preparation of evidence and settlement offers. His most important contribution was his advocacy at trial. Winston was a highly effective advocate with a good understanding of the law and the complex factual background. He was able to use his knowledge deftly in cross-examination, including of an expert witness. We were able to achieve a great outcome for the client and an indemnity based costs award”: Toby Walker, Head of Dispute Resolution, Hedges Law

“We are very grateful to Mr Jacob for his assistance and confirm that our client was very happy with the outcome”: Mary Rouse, Senior Associate, Wright Hassall LLP

“Winston was absolutely brilliant and we would very much like to keep him on board for the entirety of this case if at all possible”: lay clients

Further information


  • 2005                Called to the Bar (Middle Temple)
  • 2004-2005       Bar Vocational Course (Very Competent)
  • 1997-2000       Balliol College, University of Oxford, MA (Hons) in Jurisprudence


  • Chancery Bar Association


Prior to joining Chambers Winston worked as a solicitors’ agent, attending hearings on a daily basis in the County Courts and the Royal Courts of Justice in property, insolvency, consumer credit, contract and debt recovery matters.

He has also previously worked in the Commercial Litigation Department of Norton Rose and in the Insurance/Reinsurance Department of CMS Cameron McKenna.

Immediately after university, he spent one year as Editor of the Jersey Law Reports, reporting judicial decisions of the Jersey Royal Court and appeals to the Jersey Court of Appeal and the Privy Council in matters such as financial regulation, trusts, bankruptcy and insurance, as well as chronicling most important rulings on criminal law, procedure and evidence.

Winston has a broad commercial litigation practice involving regular appearances in the County Court and the High Court. His experience includes sale of goods and services, bailment, agency, insurance and debt recovery.

He has extensive experience of commercial debt recovery proceedings. His clients include banks and other financial organisations, insurance companies, partnerships and sole traders.

His commercial practice includes the following core areas:

  • Commercial debt recovery
  • Consumer credit agreements
  • Finance agreements
  • Guarantees and indemnities
  • Insolvency (personal and corporate)
  • Insurance
  • Partnership disputes
  • Professional negligence
  • Sale and supply of goods and services
  • Shareholder disputes

Examples of his work:

  • Acting as junior counsel in a High Court fraud claim relating to a scrap metal joint venture. 3 week trial due to start in December 2020.
  • Acting for commercial property consultants in fee claim for over £600,000 for a business rates reduction service.
  • Acting for claimant sub-contractor in claim for unpaid commission, estimated at between £100,000 to £300,000, for sales leads provided. Settled on favourable terms at the door of the court.
  • Representing defendant partners in a partnership dispute involving a jointly-owned mixed use property worth around £265,000 rented out for profit. Dispute as to whether property should be sold on open market or the defendants permitted to buy out the claimant’s interest at a valuation. Settled on favourable terms.
  • Acting for commercial property consultants in quantum meruit claim for over £150,000 for services on aborted lease negotiation.
  • Representing company director in High Court claim to rectify the register and for injunction against another director following alleged unlawful filings at Companies House terminating directors’ appointments.
  • Acting in claim on a home-insurance policy defended by insurer alleging claim forfeited due to insured’s use of a fraudulent device.
  • Representing finance company in dispute with individual who hired a car on hire-purchase. Successfully obtained an order striking out allegations of misrepresentation, duress and improperly executed agreement made in the defence and counterclaim.
  • Representing Defendant company in successful application for wasted costs of over £50,000 against the Claimant’s solicitor.

News & Resources

*This barrister is authorised to practice in England & Wales. Click here to search on the Bar Standards Board Barristers’ Register.

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