Overview

Rupert is described in Chambers & Prs as “a fantastic barrister all round”.  He is recommended by Legal 500 for Private Client: Trusts and Probate; by Legal 500 Caribbean for his offshore work and by Chambers UK Bar and Chambers HNW for Traditional Chancery.

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).

Rupert has a substantial offshore practice relating to all of his areas of specialism.  He has recently advised in relation to matters in jurisdictions including the Cayman Islands, the British Virgin Islands, Hong Kong and Gibraltar.

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.

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.

Directory recommendations

Rupert is recommended by Legal 500 UK Bar for Private Client: Trusts and Probate (tier 4); by Legal 500 Caribbean for his offshore work and by Chambers UK Bar and Chambers HNW for Traditional Chancery.

Rupert is very client-focused and clear in his advice and support.  He is approachable and good at managing expectations.” (Legal 500)

You can rely upon Rupert to provide sensible and practical advice and steer the case where required. He is always prompt in his dealings and prepared to put himself out to help. He is a fantastic barrister all round with great experience in all manner of estate disputes.” (Chambers UK Bar)

His advocacy both oral and written is really excellent.” (Chambers UK Bar)

Rupert is a solid and reliable junior with a good eye for both tactical and legal considerations.” (Legal 500 Caribbean)

“Rupert provides clear and pragmatic advice.” (Chambers HNW)

Rupert has an excellent ability to highlight the strengths and weaknesses of both the client and the other side’s claim.  He always provided clear and pragmatic advice to the client.” (Legal 500)

He is very receptive and has a very good strategy side in terms of looking at the bigger picture.” (Chambers HNW)

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)

His work is first class, really detail-orientated.  His advocacy both oral and written is really excellent.  He is a conscientious barrister.” (Chambers HNW)

 

Cases of interest

Cases of Interest

At the London Bar

Contentious Trusts and Estates

  • Re Hyatt deceased (2022-23): Acting for the Defendant in relation to a claim that a Will was invalid for want of knowledge and approval.  The case settled shortly before trial in April 2023
  • Re Freiman deceased (2020-23): Acting for the Defendant in relation to a claim to revoke a grant of letters of administration on the alleged basis that the deceased died testate, in circumstances in which the validity of the purported Will is disputed
  • Laird v Simcock [2022] EWHC 1865 (Ch), [2022] EWHC 2293 (Ch), [2022] EWHC 3237 (Ch):  Acting for three beneficiaries of a family Will trust in relation to the careless execution of a deed of appointment by the trustees.
  • Ashton v Brackstone ([2020] Lexis Citation 318): Appearing for the successful claimant regarding the construction of a Will and the application of s33 Wills Act 1837.
  • 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
  • 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

Commercial

  •  Medsted Associates Limited v Canaccord Genuity Wealth (International) Limited [2018] 1 WLR 314 (Teare J), [2019] 1 WLR 4481 (Court of Appeal), [2020] 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
  • 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

Offshore

  • Fortunate Drift Limited v Canterbury Securities Limited (2023):  Acting with Stephen Atherton KC, Mark Baldock, and Katie Pearson of Claritas in proceedings in the Cayman Islands Grand Court, including a two-week trial in June 2023.  Pleaded causes of action included conversion, breach of fiduciary duty, breach of contract and unjust enrichment
  • Kuwait Ports Authority v Walkers (2021-23) Acting in relation to a $60 million claim against a Cayman Islands law firm.  The team is led by Ben Hubble KC
  • Arnage v Walkers (2021-22) Acting in relation to a $490 million claim against a Cayman Islands law firm arising out of the uncovering of alleged frauds in a major Brazilian bank.  The team was led by Mark Simpson QC
  • 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 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] [2016] 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:

  • Advising Chevron Ltd in relation to civil and criminal proceedings relating to the massive explosion and fire at the Buncefield oil depot in Hertfordshire in 2005. The reported decisions include those at [2010] EWCA Civ 180 and [2009] EWHC 540 (Comm)

Memberships

  • Gray’s Inn
  • Chancery Bar Association
  • COMBAR

Education

  • BA (first class) University of Durham

Personal interests

Literature; long distance running; golf; watching rugby, football and cricket.