Winston Jacob

Winston specialises in property, commercial and insolvency litigation. He provides advice, drafting and advocacy to clients across these specialisms. He has appeared as sole counsel at all levels up to and including the Supreme Court. Winston is ranked as a Leading Junior in Property Litigation by the Legal 500.

Winston has developed a particular specialism in right to manage. He appeared for the successful Respondent RTM company in the Supreme Court in A1 Properties (Sunderland) Ltd v Tudor Studios RTM Co Ltd [2024] UKSC 27; [2025] A.C. 1075, an important authority on statutory interpretation and failures to comply with statutory notice procedures. In June 2025, he appeared in the Court of Appeal in Avon Freeholds Ltd v Cresta Court E RTM Co Ltd [2025] EWCA Civ 1016; [2025] H.L.R. 44, an important decision on what constitutes a “qualifying tenant” and the consequences of failing to serve a notice upon such a tenant. On 27 November 2025, the Supreme Court granted permission to appeal. Winston will be appearing again in the Court of Appeal for the Appellant in an appeal of the Upper Tribunal’s decision in The Courtyard RTM Co Ltd v Rockwell (FC103) Ltd [2025] UKUT 39 (LC); [2025] H.L.R. 23 in April 2026.

Please click on a specialism link below for more details of his experience in the relevant practice area.

Winston is valued by his clients for his comprehensive advice and thorough preparation for court appearances. He has provided insolvency training to internal lawyers at the Bar Standards Board. He has provided lectures on various topics to solicitors, corporate lay clients and the judiciary. He edits the Tenant arrears and bankruptcy section of the RICS isurv website.

Winston accepts direct instructions on a public access basis.

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

His reported cases include:

Avon Freeholds Ltd v Cresta Court E RTM Co Ltd [2025] EWCA Civ 1016; [2025] H.L.R. 44: representing the Respondent. The Court of Appeal held that an equitable tenant can be a qualifying tenant under s. 75(2) of the Commonhold and Leasehold Reform Act 2002. Further, a RTM company’s failure to serve a notice of invitation to participate on a qualifying tenant invalidates its right to manage claim. On 27 November 2025, the Supreme Court granted the Respondent permission to appeal.
The Courtyard RTM Co Ltd v Rockwell (FC103) Ltd [2025] UKUT 39 (LC); [2025] H.L.R. 23: representing the Appellant. The Upper Tribunal gave important guidance on the tests of “vertical division” and capacity to be “redeveloped independently” in s. 72(3)(a)-(b) of CLRA 2002. Winston is acting in a pending appeal to the Court of Appeal.
Avon Freeholds Ltd v Cresta Court E RTM Co Ltd [2024] UKUT 335 (LC); [2025] 1 WLR 1262: representing the successful Respondent.
Rahman v Munim [2024] EWCA Civ 123; [2025] 1 BCLC 1: acting for Appellant in Court of Appeal on appeal against dismissal of unfair prejudice petition. Consideration of whether the trial was fair in light of judicial findings of fact that were un-pleaded and/or not fully explored in cross-examination.
A1 Properties (Sunderland) Ltd v Tudor Studios RTM Co Ltd [2024] UKSC 27; [2025] A.C. 1075: the Supreme Court considered the proper approach for ascertaining Parliament’s intention as to the consequences of failing to comply with the right to manage legislation and upheld the Upper Tribunal’s decision by way of a leapfrog appeal.
A1 Properties (Sunderland) Ltd v Tudor Studios RTM Co Ltd [2023] UKUT 27 (LC); [2023] L. & T.R. 11: following Elim Court v Avon Freeholds [2017] EWCA Civ 89, the Upper Tribunal considered that an RTM company’s failure to serve a claim notice on an intermediate landlord with no management responsibilities did not invalidate its claim, whether or not the failure was deliberate. The Supreme Court upheld the Upper Tribunal’s decision, although for reasons different to the decision in Elim Court.
Yasin v Whitmore Law Solicitors [2021] EWHC B30 (Costs); [2021] Costs LR 1219: Supreme Court Costs Office held that a client could request detailed assessment of a solicitor’s gross sum bill under s. 64(3) of the Solicitors Act 1964 more than 12 months had passed since delivery of the bill and no special circumstances existed to justify assessment under s. 70(2)-(3).
Q Studios (Stoke) RTM Co Ltd v Premier Grounds Rent No. 6 Ltd [2020] UKUT 197 (LC); [2020] H.L.R. 44: Upper Tribunal considered what constitutes a flat for the purposes of the Commonhold and Leasehold Reform Act 2002, s. 112(1), and when premises are occupied for residential purposes within meaning of 2002 Act, Sch. 6.
Elim Court RTM Co Ltd v Avon Freeholds Ltd [2017] EWCA Civ 89; [2018] Q.B. 571: Court of Appeal considered the correct approach to non-compliance with statutory notice provisions in context of notices seeking the right to manage.

Feedback

‘Winston’s mental agility and general versatility enable him to quickly adapt to new situations and sudden changes in strategy of opponents. He is rarely wrong-footed’: Legal 500

‘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, Instructing Solicitor

‘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, Instructing Solicitor

Further information

Qualifications

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

Memberships

COMBAR
Chancery Bar Association
Property Bar Association

Background

Before joining the Bar, Winston worked in the Commercial Litigation Department of Norton Rose and in the Insurance/Reinsurance Department of CMS Cameron McKenna.

Insolvency

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 his 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.

Seminars/Training

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.