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 is regularly instructed in landlord and tenant matters. He appeared for the successful Appellant in the Court of Appeal in Elim Court RTM Co Ltd v Avon Freeholds Ltd [2017] H.L.R. 18; [2017] EWCA Civ 89, a case concerned with non-compliance with the statutory notice requirements in the right to manage legislation. The Respondent sought permission to appeal from the Supreme Court and Winston drafted notice of objection. Permission to appeal was refused.

His residential landlord and tenant experience encompasses claims involving all manner of tenancies, including assured and assured shorthold tenancies, secure tenancies, regulated tenancies under the Rent Act 1977, introductory tenancies and tenancies attracting no security of tenure.

He acts in possession claims (including forfeiture), service charge disputes, breach of covenant claims, and applications for antisocial behaviour injunctions.

He also acts in disputes involving business tenancies regulated by the Landlord and Tenant Act 1954, including business tenancy renewals.

His landlord and tenant practice includes the following core areas:

  • Applications to commit for contempt of court for breach of injunction
  • Breach of covenant (including disrepair)
  • Business tenancy renewals under Part II of the Landlord and Tenant Act 1954
  • Enfranchisement and right to manage
  • Possession claims (including forfeiture, s. 21 Housing Act 1988, s. 8 Housing Act 1988, s. 83 Housing Act 1985, s. 127 Housing Act 1996, NTQ and trespass)
  • Service charges
  • Tenancy deposit disputes under the Housing Act 2004

Examples of his work:

  • Elim Court RTM Co Ltd v Avon Freeholds Ltd [2017] H.L.R. 18; [2017] EWCA Civ 89: representing successful RTM company in claim for determination that it was entitled to acquire the right to manage; consideration of the court’s approach to non-compliance with statutory notice provisions.
  • Q Studios (Stoke) RTM Co Ltd v Premier Grounds Rent No. 6 Ltd [2020] UKUT 197 (LC); [2020] H.L.R. 44: representing successful applicant claiming the right to manage; consideration of what constitutes a flat for the purposes of Commonhold and Leasehold Reform Act 2002, s. 112(1), and when premises are occupied for residential purposes within meaning of 2002 Act, Sch. 6. Drafted statement of reasons why permission to appeal should be refused by Court of Appeal. Permission to appeal was refused.
  • Representing former tenant’s trustees in bankruptcy in successful application to set aside forfeiture and restore a long-lease to the register.
  • Representing successful defendant tenant, both at first instance and on appeal, to a claim for possession on grounds of forfeiture due to rent arrears. The court accepted the defendant’s argument that the ‘costs of the action’ within s. 138(2) of the County Courts Act 1984 were fixed costs under CPR Part 45 as opposed to indemnity costs.
  • Representing landlord in an arbitration to determine the terms of a tenancy under the Agricultural Holdings Act 1986.
  • Representing claimant landlord in 4-day trial of possession claim based on rent arrears and alleged breach of covenant not to part with possession; counterclaim for disrepair, nuisance and tenancy deposit penalty.
  • Advising and representing numerous landlords claiming possession under s. 21 of the Housing Act 1988 facing technical defences based on tenancy deposit legislation.

News & Resources

Managing Expectations

23rd September 2020

Read more »

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

Back to People


Richard Power

Richard Power

Head of Chambers

Call: 1983

Antonio Bueno QC

Antonio Bueno QC

Call: 1964, QC 1989

Our Expertise