Rupert has acted in numerous civil fraud claims and recently returned from a six-week trial in the Cayman Islands of a large and complex fraud claim. Rupert is particularly valued for his strong work ethic and commitment to his cases, as well as his understanding of concepts relating to accounting and valuation, which are invaluable in cases involving difficult issues in relation to assessment of damages or that involve following or tracing of assets.

• Ascentra Holdings, Inc. (in Official Liquidation) v Yoshida (Cayman Islands) – acted for the official liquidators in a claim against a former director concerning disputed ownership of shares and assets worth approximately US$250m, leading to an expedited six-week trial in the Cayman Islands in summer 2025 (led by Blair Leahy KC).
• In Re Toucan Energy Holdings 1 Ltd – instructed by joint liquidators in relation to a substantial claim against its former shareholder for alleged fraudulent trading
• Deutsche Bank AG v Sebastian Holdings Inc and Alex Vik – instructed by the former shareholder and director of SHI in relation to proceedings involving allegations that he dissipated and concealed the company’s assets, which have led to several judgments from the Commercial Court and Court of Appeal:
  • [2022] EWHC 2057 (Comm); [2023] EWCA Civ 191 – acted for contemnor in sentencing for contempt of Court and subsequent appeal against committal (led by Duncan Matthews KC)
  • [2023] EWHC 2563 (Comm) – successfully resisted application to vary the terms of a committal order (led by Tony Beswetherick KC)
  • [2025] EWHC 283 (Comm) – successfully resisted application for a second Part 71 Order (led by Tony Beswetherick KC)
• Sebastian Holdings Inc v Sarek Holdings Ltd (Turks & Caicos Islands) – acting for a former shareholder and director, defending claims for alleged dishonest breaches of fiduciary duties and misappropriations of the company’s assets (led by Tony Beswetherick KC).
• Glen Moar Properties Ltd (in liquidation) v McNally (Isle of Man) – instructed by the liquidators of several BVI companies in claims for fraudulent breaches of fiduciary duties and misappropriations by former directors (with Blair Leahy KC).
• Chowgule & Co Pte Ltd v Shirke [2023] EWHC 2815 (Comm) – successfully defended an inter partes application for a freezing injunction arising out of a family dispute and failed business venture and allegations that the defendants had defrauded the claimant of US$128 million (led by Harish Salve KC).
• Freezing Injunction – obtained a worldwide freezing injunction against “persons unknown” for the victim of a business email compromise and payment redirection fraud and associated Bankers Trust relief against banks to which funds were paid.
• In Re Yeowart – acted for the trustees in bankruptcy of former directors of companies who had perpetrated a double-financing fraud worth an estimated £250m (with Blair Leahy KC).
• In Re Smith – instructed (with Martin Pascoe QC and Blair Leahy) by the liquidators of several BVI companies which were the holding companies for a larger corporate group which had been misappropriated and then stripped of their assets by a convicted fraudster and his accomplices, which claims were part of a seven week trial before Foxton J in 2021 ([2021] EWHC 1272 (Comm)).
• Primeo Fund v HSBC Securities Services (Luxembourg) (Cayman Islands Grand Court, 23 August 2017) – complex claim worth approximately US$2bn brought by insolvent investment fund against its custodian and administrator following discovery that it had been a victim of the infamous Ponzi scheme operated by Bernard Madoff (while on secondment to Mourant Ozannes’ Cayman Islands office). The claim involved difficult questions relating to reflective loss, as well as various interlocutory issues concerning the powers and obligations of the fund’s liquidators.
• Acted on a complex claim by an insolvent investment fund arising out of a fraud by its founders and directors in which over £200m was stolen (led by Blair Leahy). The matter involved significant forensic accounting evidence, complex issues in relation to the assessment of damages, and potential claims against the fraudulent directors, non-executive directors, auditors and solicitors.

Rupert has worked on a broad range of disputes between shareholders, companies and/or their directors, often in the context of civil fraud claims by insolvent companies against former officers. He has been instructed as junior counsel on several large and complex matters and, in 2016, he spent six months in the Cayman Islands on secondment to Mourant Ozannes, where he was part of the team working on Primeo Fund’s $2bn claim against HSBC subsidiaries.

• Sian Participation Corp v Halimeda International Limited (BVI Court of Appeal and Privy Council) – appeared for the successful respondents on an appeal against an order that the appellant should be put into insolvent liquidation on the basis that the debt was disputed and the appellant had a claim against the respondent that was worth more than the debt (led by Paul Lowenstein KC).
• Acted for the former director and shareholder of a company that had been the victim of a fraud in defending a claim brought by the company’s liquidators. Claim discontinued by the liquidators.
• Unfair prejudice petition – instructed to defend a petition issued following a catastrophic breakdown in relations between shareholders (led by Blair Leahy). The case involved difficult questions over valuation, complicated by the parties’ wildly different views on value. Settled at mediation.
• Acted for the defendant to a claim brought by a former director and shareholder for alleged breach of conduct following his removal from office for alleged gross misconduct. Settled at mediation.

Rupert regularly advises and appears in commercial disputes of all kinds, including contractual disputes and tortious and other claims arising out of commercial relationships.

Some examples include:

• Instructed by the former lessee of a commercial airliner in relation to disputes with the owner/lessor concerning the late redelivery of the aircraft and its condition on redelivery (led by Timothy Young KC).
• Instructed by the owner of a private jet in relation to an arbitration claim by an intended purchaser for alleged breach of an aircraft purchase agreement.
• Acted for a major African conglomerate successfully defending an arbitration claim by a construction company in respect of a cancelled contract for construction of storage domes at ports in Nigeria.
• Lemos v Lemos – Acted for claimants in a complex dispute concerning ownership and control of a family business (led by Tom Raphael QC). The case raised issues of Greek and Liberian law, as well as issues relating to the administration of wills.  Claim settled.

Arbitrations account for a significant part of Rupert’s practice. He is often instructed as sole counsel, although he has also been led by prominent silks on high value arbitrations (LCIA, UNCITRAL, LMAA, BVI IAC). He recently acted for MSC (led by Julian Kenny QC) in a complex and document-heavy arbitration concerning the explosion of undeclared dangerous goods on board the MSC Flaminia while the vessel was in the mid-Atlantic.

Rupert is also regularly instructed on applications to Court in relation to arbitration proceedings, including challenges to awards under s.68 of the Arbitration Act and applications for leave to appeal against awards under s.69 (including a highly unusual application for leave to appeal to the Court of Appeal in respect of an unsuccessful s.69 application for leave to appeal). He has appeared unled in both the Commercial Court and Court of Appeal on such applications. Rupert has also been involved in an application made to Court in support of arbitration proceedings in order to obtain an order for sale of cargo on board a vessel.

Significant cases, and examples of other recent instructions, include:

• Section 68 Application – Acting for an unsuccessful claimant challenging an arbitration award on grounds of serious irregularity.
• UNCITRAL Arbitration – Acted for an investment management firm in a claim for payment of deferred consideration due in respect of an investment made by the respondents, in a claim that involved allegations of market manipulation of the share price of a publicly listed company and breach of an express obligation of good faith (led by Paul McGrath KC).
• Ad hoc Arbitration – MSC Flaminia – Acted for charterers in a claim by owners of a container vessel for loss and damage of US$200m caused by explosion of containers of divinylbenzene (DVB) while the vessel was at sea (led by Julian Kenny KC).
• LCIA Arbitration – Instructed by the owner of a private jet in relation to a claim by an intended purchaser for alleged breach of an aircraft purchase agreement.
• BVI IAC Arbitration – Acted for a major African conglomerate defending a claim by a construction company in respect of a cancelled contract for construction of a port storage facility.
• LMAA Arbitration – Instructed by shipowners in a claim against charterers for loss and damage caused by a fire started while the vessel was loading cargo.
• LMAA Arbitration – Acted for charterers defending an unsafe port claim by owners for damage caused to a vessel while berthing.
• ICC Arbitration – Acted for a steel producer in an arbitration claim brought by a purchaser for breach of an exclusivity provision which precluded the seller from shipping any other cargo to the market where the purchaser operated for a period of three months.
• LMAA Arbitration – Acted for claimants in a series of document-heavy and factually-intricate arbitrations with a total combined value in excess of US$30m (led by Philip Edey QC).
• Dainford Navigation v PDVSA [2017] 2 Lloyd’s Rep. 409 – Instructed by claimants on a s.44 application brought in support of arbitration proceedings for sale of a cargo subject to arrest and lien as security for a claim against charterers (led by Michael Coburn QC).
• Section 69 Application – Instructed by an unsuccessful respondent, who was subject to an award for over $45m, on a unique application to the Court of Appeal challenging a High Court judge’s refusal of leave to appeal on an application made under s.69 of the Arbitration Act (led by David Joseph QC). The case settled before the application was heard by the Court of Appeal.
• Frontier Agriculture v Bratt Brothers [2015] 2 Lloyd’s Rep. 500 (CA) – an application to enforce an award under section 66 of the Arbitration Act which turned on questions concerning whether the respondent had participated in the arbitration, and on whether the respondent had adduced sufficient evidence to call into question the existence of the arbitration agreement.
• The “Astra” [2013] 2 All E.R. (Comm) 689 – Instructed on the successful application for leave to appeal under section 69 of the Arbitration Act, which led to the controversial (now overruled) decision by Flaux J concerning whether prompt payment of hire is a condition of a charterparty (assisting Josephine Davies KC).

Rupert has a busy shipping and international trade practice and is frequently instructed by shipowners, charterers, cargo interests, buyers, sellers and others besides in relation to all manner of disputes falling within these spheres.  As well as undertaking many cases as sole counsel, he is regularly instructed as a junior to silks in Chambers in relation to high value and complex matters.

Significant cases, and examples of other recent instructions include:

• Maersk AS v Mercuria Energy Trading SA [2021] EWHC 2856 (Comm) – Acted (led by Michael Collett QC) for the purchasers of a cargo of copper ingots, who were the victims of a cargo substitution fraud, as respondents to an application by the carriers for an anti-suit injunction.
• MSC Flaminia – Acted (led by Julian Kenny QC) for the charterers in an arbitration claim by owners of a container vessel for loss and damage of US$200m resulting from an explosion on board caused by autopolymerisation of undeclared cargoes of divinylbenzene (DVB) while the vessel was at sea.
• Acted for shipowners in an arbitration claim against charterers for loss and damage caused by a fire started while the vessel was loading cargo.
• CMA CGM SA v Nile Dutch Africa Line BV – Acted (with Michael Collett QC) for charterers of a container vessel defending a claim by owners for loss and damage caused by explosion of an undeclared cargo of sodium hypochlorite. Claim Settled.
• Acted for a steel producer in an arbitration claim brought by a purchaser for breach of an exclusivity provision which precluded the seller from shipping any other cargo to the market where the purchaser operated for a period of three months.
• Acted for shipowners in a series of arbitrations with a total value in excess of US$30m, involving claims for unpaid hire and other sums due under a number of charterparties (led by Philip Edey QC).
• Dainford Navigation v PDVSA [2017] 2 Lloyd’s Rep. 409 – junior counsel for owners on a s.44 application for sale of a cargo subject to arrest and lien as security for a claim against charterers (led by Michael Coburn QC).
• San Evans Maritime v Aigaion Insurance Co [2014] 2 Lloyd’s Rep 265 – appeared for the successful claimant in a dispute concerning the meaning and effect of a “follow clause” in a marine insurance policy following grounding of a vessel (led by Michael Ashcroft QC).
• The “Astra” [2013] 2 All E.R. (Comm) 689 – formerly a leading case on the controversial question of whether prompt payment of hire is a condition of a charterparty (assisting Josephine Davies).
• Yilport Konteyner Terminali v Buxcliff [2013] 1 Lloyd’s Rep. 378 – appeared for the successful claimant port operator in a claim for port charges for discharging cargo from a holed vessel (led by David Lewis QC).