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 has appeared as an advocate twice in the Supreme Court. 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. On 7 July 2026, he appeared for the Appellant, leading Christian Fox of Lamb Chambers, in an appeal of the Court of Appeal’s decision in Avon Freeholds Ltd v Cresta Court E RTM Co Ltd [2025] EWCA Civ 1016; [2026] 1 W.L.R. 166. The issue is whether a landlord can rely on an RTM company’s failure to serve notice on a qualifying tenant to oppose acquisition of the right to manage. The Supreme Court’s reserved judgment is expected later this year.

In April 2026, he appeared for the Appellant RTM companies in the Court of Appeal in The Courtyard RTM Company Ltd v Rockwell (FC103) Ltd [2026] EWCA Civ 712. The Court of Appeal gave guidance on the test for a self-contained part of a building in s. 72(3) of the Commonhold and Leasehold Reform Act 2002.

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; [2026] 1 W.L.R. 166: 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. The Supreme Court will hear an appeal on the second issue on 7 July 2026.
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.

Commercial

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:

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.
Ahmed v Munim: acting for appellant in appeal to Court of Appeal against High Court’s dismissal of unfair prejudice petition. Drafted Amended Grounds of Appeal and supporting skeleton argument, following which permission to appeal was granted on all amended grounds. Appeal was settled after appellant obtained permission to appeal.
Aries Robotics Plc v Persons Unknown: acted for Appellant seeking permission to appeal from Court of Appeal against discharge of interim injunction against alleged blackmailers. The appeal concerned the extent of the court’s jurisdiction to maintain an interim injunction prior to service of the claim form. Drafted skeleton argument in support of request for permission to appeal, following which the Court of Appeal granted permission to appeal. The parties subsequently settled.
La Cotte Consulting Ltd v Sovereign Steel Stockholders: appeal to Court of Appeal of indemnity costs order following trial. Permission to appeal obtained. Settlement reached shortly before appeal hearing due to take place.
La Cotte Consulting Ltd v Sovereign Steel Stockholders [2021] EWHC 1517 (Ch): representing claimant claiming fraud, mistake, unlawful means conspiracy and procuring breach of contract in relation to allege scrap metal business joint venture, including 3-week High Court trial.
Yasin v Whitmore Law Solicitors [2021] EWHC B30 (Costs); [2021] Costs LR 1219: representing successful claimant seeking detailed assessment of solicitor’s gross sum bill under s. 64(3) of the Solicitors Act 1964 where more than 12 months had passed since delivery of the bill and no special circumstances existed to justify assessment under s. 70(2)-(3).
Acting for commercial property consultants in fee claim for over £600,000 for a business rates reduction service.
Acting for unregulated lender in 3-day trial of claim for repayment of over £380,000 for bridging loan advanced on basis of declaration that intended for business purposes. Defence and Counterclaim alleging that agreement unenforceable under s. 26 of FSMA 2000 as a regulated mortgage contract; alternatively, an unfair relationship under s. 140A(1) of CCA 1974.
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.

Consumer credit

Winston provides representation and advice in claims involving all aspects of the Consumer Credit Act 1974 and related legislative provisions. He has represented banks and other financial institutions in claims relating to consumer credit and consumer hire agreements. His experience includes:

Improperly executed regulated agreements
Regulated hire purchase and hire agreements
Regulated mortgages
Unfair relationships (ss. 140A-C)

Examples of his work:

Representing mortgagee in possession claim defended on basis that the mortgage was unenforceable under s. 26 of the Financial Services and Markets Act 2000 as a regulated mortgage contract made by an unregulated lender. Reserved judgment is due to be delivered in January 2022.
Representing different mortgagees in a number of possession claims defended, among other matters, on grounds that the agreement was an unfair relationship within the meaning of s. 140A of the 1974 Act
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.
Advising an unincorporated association regarding its potential liability under a regulated hire agreement.
Drafting defence to a claim on a regulated hire agreement raising issues of enforceability of the agreement under ss. 86D and 87 of the 1974 Act.