Rupert is a chancery and commercial barrister and a former solicitor and Cayman Islands attorney. He is described by Legal 500 2022 as a “Rising Star” for Private Client: Trusts and Probate at the London Bar.
Rupert specialises in trusts, probate and estates disputes, including cases concerning the validity or otherwise of Wills and inter vivos transactions, construction and rectification applications, breach of trust claims, applications for the removal or substitution of trustees and personal representatives and applications under the Inheritance (Provision for Family and Dependants) Act 1975. He also has a broad commercial practice encompassing contractual, company and partnership disputes, professional negligence, fraud and asset tracing and insolvency (both corporate and individual).
Prior to joining Chambers, Rupert was a senior associate in the Cayman Islands office of the market-leading offshore firm Appleby. He had full admission to the Cayman Islands Bar from 2010-2016 and appeared in many of the most significant cases in the jurisdiction during that period, including cases in the Cayman Islands Court of Appeal and the Privy Council. On one occasion he cross examined a hedge fund director in the Oslo City Court in Norway.
Before moving to Appleby, Rupert trained and practised as a litigation solicitor, and subsequently as a solicitor-advocate, with Herbert Smith LLP in London from 2005-2010.
- What the directories say
- Very user friendly, good with clients and a wealth of trust experience. Always approachable and advises on the most technical of matters with ease. Legal 500 2022
- Cases of interest
Cases of Interest
At the London Bar
- Medsted Associates Limited v Canaccord Genuity Wealth (International) Limited  1 WLR 314 (Teare J),  1 WLR 4481 (Court of Appeal),  EWHC 2952 (Comm) (Nicholas Vineall QC): Advising and acting for the defendant, a Jersey-based wealth manager, in long-running litigation brought by a BVI-incorporated introducing broker. The case encompassed Commercial Court and Court of Appeal proceedings on issues of liability concerning the fiduciary duties of brokers, Commercial Court quantum proceedings, and contested interlocutory proceedings, including in relation to security for costs, specific disclosure and leave to adduce additional witness evidence a week before trial. Rupert acted as part of a counsel team including, at various times, Hodge Malek QC, Robert Hantusch, Matthew Slater and James Potts
- Ashton v Brackstone (High Court, unreported, 23 September 2020): Appearing for the successful claimant regarding the construction of a Will and the application of s33 Wills Act 1837
- Re a Cayman Islands Trust (2020): Advising a Cayman Islands trustee of a £20m trust in relation to allegations of breach of trust and gross negligence. The case also involved allegations of undue influence, lack of capacity, proprietary estoppel and conspiracy
- Re Fleming deceased (2020): Advising and appearing in a claim for the removal of a personal representative
- Re Fitzgerald deceased (2019-2020): Acting in a probate dispute regarding the validity of a Codicil. The case involved allegations of lack of capacity, want of knowledge and approval and undue influence; also removal of a personal representative
- Re Mehmi deceased (2017-2020): Acting and appearing in a claim to remove a personal representative and defending a proprietary estoppel claim against the deceased’s estate
- Carter v Carr (2019): Advising in relation to a dispute between two co-trustees of a £12m family trust, each claiming for the other’s alleged breach of trust and removal as a trustee
- Re Quin deceased (2019): Acting for the claimant, a former co-habitee of the Deceased, in a 1975 Act claim
- Re Kendrick deceased (2019): Advising and appearing in a claim for the removal of a personal representative
- Re a Family Farming Partnership (2018-19): Acting for the successful claimant in a confidential arbitration (HH Peter Langan QC) concerning a dispute between the estates of two deceased family members, both of whom were partners in a family farming partnership, with regard to the sizes of their respective interests
- Grindy v Perry (2018): Acting in a probate dispute regarding the validity of a Will. The case involved allegations of lack of capacity, want of knowledge and approval and undue influence
- Page v Bentham (2017): Acting in a probate dispute regarding the validity of a Will. The case involved allegations of lack of capacity, undue influence and fraudulent calumny
- Re Hinds (2016-17): Advising (led by Robert Ham QC) a Cayman Islands individual in relation to an application to the Privy Council for special leave to appeal a decision of the Cayman Islands Court of Appeal in succession proceedings
As a Cayman Islands attorney:
- Ennismore Fund Management Limited v Fenris Consulting Limited [2012(1) CILR 84], [2014(1) CILR 357]  UKPC 9: Advising and appearing as junior counsel (led by Mark Cunningham QC) for Ennismore Fund Management Ltd in relation to a dispute with Fenris Consulting Ltd in proceedings before the Grand Court, the Cayman Islands Court of Appeal and the Judicial Committee of the Privy Council
- In Re WGF Feeder Fund (in Official Liquidation): Acting for the liquidators of a Cayman Islands mutual fund with regard to the liquidation, including conducting the statutory examination of a director in the Oslo City Court in Norway, and advising in relation to the issue of fraud and asset tracing proceedings in Singapore
- In Re Trikona Advisers Limited (in Official Liquidation): Acting for the liquidators of a Cayman Islands holding company, in particular with regard to proceedings involving the company in the United States (Connecticut and New York), England, Mauritius, India and Singapore
- In Re Orchid Developments Limited (in Official Liquidation): Acting for the liquidators of a Cayman Islands company, in particular with regard to the asset sale of its real estate portfolio in continental Europe
- Navarro Wieler and others v HSBC International Trustee Limited and Wieler Velarde: Advising and appearing (with Carlos de Serpa Pimentel) for an institutional trustee in relation to a family trust dispute, in the context of proceedings in the United States and Bolivia, with regard inter alia to forum issues.
- Helmsman Limited and another v Bank of New York Trust Company (Cayman) Limited: Advising (with Robert Ham QC and Carlos de Serpa Pimentel) for two trust companies in relation to an allegation of breach of trust against a predecessor trustee
- In Re Times Property Holdings Limited [2011(1) CILR 223]: Advising and appearing (with Jeremy Walton) for Times Property Holdings Limited in opposing a winding up Petition in proceedings before the Grand Court. The Petition was presented on the basis of an alleged debt of approximately US$445 million, in the context of related proceedings in the British Virgin Islands and Hong Kong
- In Re GFP Dunas Partners Holdings, Inc [2011(1) CILR N10]: Advising and appearing (with James Corbett QC and Graeme Halkerston) for a shareholder of GFP Dunas Partners Holdings, Inc in successfully obtaining a winding-up Order against that company on the just and equitable ground in proceedings before the Grand Court
- Thompson (A.L.) Bldg. Supplies Ltd. v Beazley Underwriting Ltd. and Ors [2011(2) CILR 496]: Advising and appearing (with Jeremy Walton) for the Respondents in successfully defending a claim for an order that an arbitral costs award be set aside in proceedings before the Grand Court
- Advising and appearing as junior counsel (led by Catherine Newman QC) for a Japanese trustee in bankruptcy in relation to a dispute over ownership of units in two unit trusts governed by Cayman Islands law
- Advising and appearing as junior counsel (led by Robert Ham QC on appeal and by Peter McMaster QC at first instance) for a beneficiary in relation to a deceased’s estate in proceedings before the Grand Court and Cayman Islands Court of Appeal.
As an English solicitor:
Chancery Bar Association
BA (first class) University of Durham
- Personal interests
Literature; long distance running; golf; watching rugby, football and cricket.