Winston Jacob

Winston specialises in property, commercial and insolvency litigation. He provides advice, drafting and advocacy to clients across these specialisms. He has appeared 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 and the County Court 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.

Winston also specialises in Consumer Law.

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


“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 acts for creditors, debtors and insolvency practitioners in both individual and corporate insolvency proceedings.

He has considerable experience of personal insolvency, including statutory demands, bankruptcy petitions, annulment applications, and trustees’ applications for the sale of property under s. 14 of the Trusts of Land and Appointment of Trustees Act 1996 (in conjunction with s. 335A of the Insolvency Act 1986).

He also acts in winding up petitions and related applications, such as for injunctions to restrain presentation or advertisement of a petition.

Winston also acts in cases where trustees in bankruptcy seek to assert their rights against third parties, such as persons who co-own property with the bankrupt.

His clients include banks and other financial organisations, insurance companies, partnerships and all manner of creditors.

Examples of recent insolvency work

  • Obtained administration order on behalf of a company, enabling it to avoid a winding up order being made against it
  • Successfully resisted application to set aside statutory demand for sums due pursuant to a property development related loan agreement where debtor alleged that debt disputed and that had a counterclaim that exceeded its value
  • Obtained urgent injunction to restrain presentation of winding up petition in the Interim Applications Court on the basis that the alleged debt was genuinely disputed
  • Appeared for creditors and debtors in various winding up and bankruptcy petitions
  • Pickard v Roberts [2016] B.P.I.R. 996; [2016] EWHC 187 (Ch): representing bankrupt’s wife and co-owner of property seeking to set aside order for sale in favour of trustee in bankruptcy obtained at hearing which she failed to attend; consideration of what constitutes a “trial” for the purposes of CPR r. 39.3.
  • Acting for former tenant’s trustees in bankruptcy in successful application to set aside forfeiture and restore a long-lease to the register.


Winston 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.

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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Richard Power

Richard Power

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Call: 1983

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Antonio Bueno QC

Call: 1964, QC 1989

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