Tom Shepherd

Tom is ranked as a leading junior by Chambers and Partners in the field of Chancery: Commercial (2019): “An unbelievably good advocate for his level of call, who is meticulous in his preparation and completely dedicated to the case“. “He is very punchy as an advocate and very hard-working“.

Tom’s practice covers all aspects of commercial and corporate litigation. His practice draws on his experience in the fields of insolvency and company law, professional liability, civil fraud and banking / financial services. He has recently acted as junior counsel in several high-value pieces of litigation but also has considerable experience of trial advocacy on his own account.

Key cases include:

• Willers v Joyce [2018] (judgment awaited): representing the defendants in the first case in English legal history of alleged malicious prosecution of civil proceedings since the recognition of the tort by the Supreme Court [2016] UKSC 43. Five-week Chancery Division trial before Rose J. Extensive trial preparation and conducting cross-examination of factual and expert witnesses. Led by Paul Mitchell QC.
• Rollerteam Ltd v Riley [2018] EWHC 1065 (Ch): claim against shadow director for alleged misappropriation of gate receipts of the Sherlock Holmes Museum and dispute arising out of settlement agreement. Tom acted on various successful interim applications relating to the release of monies held in escrow and the sale of a substantial property under the settlement agreement, before appearing at the trial / inquiry at which the applicants’ claims succeeded in full. Led by Neil Hext QC.
• Breckons & Ors v Powerscourt Services Ltd & Ors [2015] EWHC 1330 (Ch): acting for the defendants to a claim alleging fraud and deceit in relation to an investment in farmland in Argentina. Successfully applying to strike out the claim and discharge a freezing order on the ground of material non-disclosure.
• Sharma v Sharma [2014] BCC 73, [2013] EWCA Civ 1287: successfully representing the Respondent in the Court of Appeal, subsequent to a two-week High Court trial [2012] EWHC 2529 (Fam) relating to the ownership of a multi-million-pound dental business and associated allegation of breach of fiduciary duty and diversion of corporate opportunities.
• A dispute between family members arising out of a property development business, dating back to the early 1990s. Successful strike-out of key parts of defence and resisting appeal against the same. Numerous successful applications for interim payments ahead of trial to be listed in 2019.
• A dispute between members of a substantial property consortium with a portfolio worth in excess of £20m, involving difficult issues of expert valuation evidence. Led by David Halpern QC.
• Acting for a reseller of telecommunications services in a substantial breach of contract claim (worth c.£6m) for failure to pay sums due in respect of the purchase of a large customer base and consequential losses. Led by Neil Hext QC.
• Successful pursuit of injunctive proceedings for a R&D tax specialist which had launched the first ever UK Championship of ‘Brit Pong’ – the UK version of Beer Pong – against the marketing company it had instructed to promote the event.
• A substantial partnership dispute relating to a waste oil collection and sale business. Obtained judgment subsequent to five-day trial and taking of an account, including the cross-examination of forensic accountants.
• Successfully defending a claim brought under a personal guarantee by a commercial money lender. Three-day trial involving expert handwriting evidence, the proper construction of the document under question and penalty clauses.
• Acting for a well-known high street retail pawnbroker and loan provider in a dispute arising out of a series of franchise agreements.
• Successfully defending a claim brought by a well-known bloodstock auctioneer relating to the sale of a racehorse (instructed as sole counsel). Three-day multi-track trial involving multiple claims and defendants.
• A claim brought by a well-known classic car dealer in relation to the alleged sale of a Porsche 911 1973 RSR. Three-day multi-track trial.
• A claim by a former partner against a major accounting firm for misrepresentation and negligent misstatement. Issues involved the proper construction of an LLP Deed and whether the claim was barred by the rule in Henderson v Henderson.
• Acting for the former agent of a well-known professional footballer in a $2.5 million claim relating to the exploitation of the player’s image rights and connected claims for inducing breach of contract and conspiracy.
• Advising a major software developer in relation to a dispute arising out of a multi-billion-pound government contract. Settled under confidential terms.

Tom is ranked as a leading junior in the directories:

• Legal 500: Insolvency (2019):“A very tenacious and skilful advocate but also extremely good on the law”.
• Chambers and Partners: Restructuring/Insolvency (2019): “Tom is rigorously thorough and responsive, while he also always keeps a commercial outlook and has very strong tactical judgement“. “He is very strong on his feet and has a good client manner. He is aggressive when he needs to be and sensible in his deliveries in court“.

Tom is frequently instructed in high-value, contentious insolvency matters, often with elements of fraud. Tom has appeared before the Court of Appeal (as sole counsel) and in numerous High Court trials and contested applications. Tom has experience of dealing with a wide range of corporate insolvency matters, including winding-up petitions, administrations, CVAs, injunctions to restrain presentation and advertisement of winding-up petitions, validation orders, and disputes involving transactions at an undervalue and preferences. He has particular expertise of cases involving cross-border fraud and acting in defence of claims against insolvency practitioners. Tom is happy to consider acting on a Conditional Fee Agreement, where appropriate.

Tom was appointed as Junior Counsel to the Crown (Attorney General’s B Panel) in June 2016 and has significant experience of acting for and against the Secretary of State in directors’ disqualification proceedings.

A selection of his most significant cases:

• Acting for the respondent to a claim by liquidators relating to a property portfolio worth in excess of £4 million. The claim involved allegations of forgery (including expert documentary evidence relating to Deeds of Trust), alleged transactions at an undervalue and the enforceability of security obtained pursuant to related ongoing litigation in Nigeria (including whether the English Court could go behind orders obtained in the High Court, Plateau State).
• Acting for the former director of a company which specialised in the adaptation and film production of Shakespeare plays for children, in defence of claims for alleged misfeasance, transactions at an undervalue and preferences.
• Advising a commercial lender in relation to the enforceability of certain security documentation arising out of the takeover of a well-known professional football club.
• Acting on a hotly contested, urgent pre-pack administration application involving a manufacturer and retailer of luxury handmade mobile phones.
• Defending a claim against the former administrator of a company under para 75 of Sch B1 arising out of a pre-pack sale of assets and book debts at an alleged substantial undervalue.
• Representing the Secretary of State for Business, Energy and Industrial Strategy in director’s disqualification proceedings subsequent to a £6m+ insolvency, arising out of the collapse of a plc which provided cash collection, counting, processing and banking services to a wide range of cash businesses.
• Acting on an application to restrain presentation of a winding-up petition against a substantial telecoms company.
• Advising the operating company of a major and well-known professional sports league in relation to certain prescribed consequences on the happening of an insolvency event.
• Advising a landlord on a prospective challenge to a CVA involving issues of guarantee stripping and the provision of incomplete financial information at the meeting of creditors.
• Acting for the liquidator in a successful claim to recover a yacht transferred by the company for nil consideration.
• Acting for the liquidator on a successful transaction at an undervalue and misfeasance claim: fully contested multi-track trial.
• Blue Monkey Gaming Ltd v Hudson, Bushby & Bower [2014] All ER (D) 222: successfully defending the joint administrators of a nationwide chain of amusement arcades against a multi-million-pound claim in conversion brought by a supplier of gaming machines. Two-week High Court trial.
• Bristol Alliance (No 1) Ltd & others v Bennett & Cadwallader [2013] EWCA Civ 1626: an appeal to the Court of Appeal concerning the entitlement of various parties to funds in excess of £0.5 million held in escrow by a landlord.
• Defending the director of a property services company against allegations of fraudulent and wrongful trading and breach of fiduciary duty arising out of the alleged wrongful declaration of dividends.
• Re Sidley Sports Club (Registrar Derrett, unreported, 26 July 2013): obtained a winding-up order of a sports and social club pursuant to the Court’s equitable jurisdiction. Advising the liquidator of a former development agency as to the status of certain funds and grants in excess of £3 million. Involved an alleged Quistclose trust and issues of tracing.

Tom is ranked as a leading junior in the directories:

• Legal 500: Insolvency (2019):“A very tenacious and skilful advocate but also extremely good on the law”.
• Chambers and Partners: Restructuring/Insolvency (2019): “Tom is rigorously thorough and responsive, while he also always keeps a commercial outlook and has very strong tactical judgement“. “He is very strong on his feet and has a good client manner. He is aggressive when he needs to be and sensible in his deliveries in court“.

Tom acts for and advises private individuals and insolvency practitioners on all aspects of the bankruptcy process and regularly appears before the Insolvency and Companies Court Judges. His experience includes applications to set aside statutory demands, claims for transaction avoidance, IVAs, rescission, annulment and associated applications.

A selection of his most significant cases:

• A three-day trial of a bankruptcy petition presented by HMRC involving a jurisdictional challenge under s.265 of the Insolvency Act 1986. Issues involved whether HMRC was entitled to obtain flight records under s.29 of the Data Protection Act 1998 and whether the respondent had carried on a business in the jurisdiction in the relevant period.
• Acting for the Trustee in Bankruptcy in proceedings involving the execution of bench warrants (at Heathrow airport, as the bankrupts sought to leave the jurisdiction) and subsequent conduct of three-day private examination. The upshot was the discovery of numerous assets and bank accounts in India.
• Representing a group of opposing creditors on a highly contentious and complex bankruptcy matter involving competing claims and issues of priority between three separate firms of solicitors in respect of unpaid legal fees. The case involved undertakings given in related proceedings in the Family Division and a jurisdictional challenge on the grounds of collateral purpose and improper motive.
• Ariel v HMRC [2016] EWHC 1674 (Ch): acting for a trustee in bankruptcy on an application under s.303 of the Insolvency Act 1986 relating to the service by HMRC of a third-party information notice under Sch 36 Finance Act 2008. This was the first time HMRC had served such a notice on an insolvency practitioner, notwithstanding that the power had existed for c.20 years.
• Acting for a group of opposing creditors (solicitors firms who were owed substantial fees) who objected to bankruptcy petition on the grounds of collateral purpose and improper motive. Confidential settlement achieved.
• Successful application to annul a 6-year-old bankruptcy order on the grounds of lack of capacity (owing to a long-term chronic mental impairment, which included an irrational phobia of opening mail).
• Chadwick v Burling [2015] 3 Costs LR 589: acting for the successful trustee in bankruptcy on an appeal against an order for possession and sale of two properties, subsequent to an unsuccessful application for relief from sanctions by the respondent. Warren J held that the fact that the respondent was a litigant in person could be a relevant factor only at the margins of the third stage under Denton.
• Acting for a trustee in bankruptcy on a successful claim to recover a property and substantial transfers into an Egyptian bank account.
• Defending a claim by a trustee in bankruptcy in relation to the alleged sale at an undervalue of a property subsequent to a deed of settlement and related issues involving a property and funds held in Andorra.
• Acting for the respondent to a statutory demand for c.€49m issued by an Irish Bank.
• Obtaining an order for the disclosure and production of documents by a bankrupt, and a warrant for the bankrupt’s arrest following non-compliance with the order.
• Acting for joint trustees appointed under an Insolvency Administration Order, in a claim to recover substantial sums paid as transactions at an undervalue.
• Acting for Heritable Bank plc (in administration) on an application to set aside a statutory demand for £1.3 million. Issues included a claim against the Bank for alleged interference with LPA receivers.
• Sands & Treharne v Wright [2010] BPIR 1437: defending an application by a trustee under s.284 IA for a declaration that payments made by a bankrupt were void.

Tom has vast experience of bringing and defending claims across the full spectrum of civil fraud: from highly sophisticated corporate/investment schemes and cross-border fraud in the context of a large-scale insolvency to the alleged misappropriation of hard cash (in an arcade gaming business) and physical assets (in the form of hundreds of tonnes of by-products from the steel manufacturing process at a plant in South Wales).

Tom has regularly obtained (and defended applications for) urgent freezing injunctions and search orders (including applications to discharge and vary such orders) and related interim measures.

His recent cases include:

• Celsa v Benson & Ors: representing one of seven defendants to a claim by the UK’s largest steel manufacturer for unlawful means conspiracy arising out of the alleged misappropriation of hundreds of tonnes of by-products from the steel manufacturing process at a plant in South Wales. Settled on confidential terms.
• A substantial claim against a bloodstock agent arising out of the alleged payment of secret commissions, bribes and “luck money” subsequent to the purchase of racehorses.
• Breckons & Ors v Powerscourt Services Ltd & Ors [2015] EWHC 1330 (Ch): acting for the defendants to a claim alleging fraud and deceit in relation to an investment in farmland in Argentina. Successfully applying to strike out the claim and discharge a freezing order on the ground of material non-disclosure.
• A claim against an IFA and related parties for deceit, breach of trust and dishonest assistance arising out of the misappropriation of substantial funds paid into a series of offshore investment schemes/scams. Settled on confidential terms.
• Zavgorodnya v Lever: acting for a high net worth Ukrainian citizen in a claim to recover substantial sums misappropriated in connection with a residential construction project in Knightsbridge. Successful strike-out of Defence on Day 1 of High Court Trial.
• A claim for c.£5m arising out of the misappropriation of cash and assets in a substantial adult gaming centre business, dating back to the 1980s.
• Representing two defendants in a multi-party claim for c.£20 million involving allegations of deceit and unlawful means conspiracy arising out of the alleged unauthorised lending of substantial sums to a boutique hotel operator.
• Defending a former director of a tax advisory firm against allegations of fraudulent misappropriation of sums in excess of £5 million. The case involved issues relating to the scope of a proprietary freezing injunction and the interplay between confiscation and restitution orders obtained in the Crown Court.
• Defending a claim for fraudulent misrepresentation and for deceit arising out of the sale of an international logistics company.
• Represented a Kazakh-based defendant in a multi-million-pound fraud claim brought by a Kazakh Bank against seventeen defendants.

Tom is regularly instructed in claims for and against a wide range of professionals. He has experience of actions involving auditors, accountants, investment advisors, insolvency practitioners, solicitors and IT professionals.

Recent cases include:

• Defending a claim against solicitors arising out of the alleged negligent conduct of a substantial Chancery Division claim. Led by Graeme McPherson QC.
• Acting for the claimant private investment fund on an action against solicitors arising out of the alleged negligent advice and drafting of certain transactional and security documentation for a £6m loan in connection with the proposed refinancing of a Championship football club.
• Representing the claimants in a substantial action against solicitors, tax advisors and the operators of a high-risk tax mitigation/spread-betting scheme.
• Successfully defending a claim brought by an IT services company for services allegedly provided to a major IT company in Sweden, subsequent to a three-day trial. Trial judge remarked on his “neat cross-examination” of the Claimant’s key witness.
• A claim against solicitors subsequent to an Employment Tribunal claim for caste discrimination and victimisation against the claimant’s former employers.
• A claim against tax advisors and solicitors arising out of an unsuccessful stamp duty land tax mitigation scheme.
• Defending a claim against solicitors relating to the alleged failure to conduct searches that would have revealed the existence of a sewerage pipe beneath a residential property development site. Included difficult questions relating to contemporaneous file notes and the proper approach to valuation of the site in question.
• Acting on a claim against solicitors arising out of the failure to secure a new commercial lease pursuant to the 1954 Landlord and Tenant Act.
• A claim against the administrator of a series of pensions schemes arising out of the alleged negligent miscalculation of benefits and overpayment to scheme members. Led by Graham Chapman QC.
• Defending a claim against a provider of medico-legal services.
• A claim against a leading firm of IT consultants relating to a Payment Card Industry Data Security Standard audit of a company which provided online real-time booking facilities for the UK tourist industry.
• Defending a claim against solicitors in relation to the alleged negligent drafting of a share sale agreement and failure to comply with certain provisions of the Companies Act 1985.
• A claim against patent and trademark attorneys arising out of the alleged negligent provision of advice in connection with the manufacture of satellite equipment.
• Defending a claim against a firm of solicitors arising out of the fraudulent execution of a series of mortgage deeds.
• Acting for the liquidators of a company in relation to very substantial claims in negligence against former solicitors and auditors.

Tom frequently appears on behalf of major banks and financial institutions in relation to the enforcement of guarantees, loan agreements, hire purchase agreements, claims for possession and other applications. He also has substantial experience acting for and against the Financial Conduct Authority.

A selection of his most significant cases:

• Re: a Debt Management Company (2017): successfully representing a substantial commercial debt management company on an application before the Regulatory Decisions Committee of the FCA for permission to carry out regulated activities. Tom was involved at all stages of the proceedings, which resulted in only the second such successful application at the time and a complete change of approach by the FCA to future applications.
• Acting for a commercial lender in relation to the enforceability of certain security documentation arising out of the takeover of a well-known professional football club.
• Advising the assignee of a portfolio of commercial debt in relation to remedies following the breach of a settlement agreement and the enforceability of various guarantees.
• Acting for the FCA on a claim involving a purported forex trading company/scheme. Obtaining urgent freezing and other interim relief.
• Financial Conduct Authority v Cavendish Moore Ltd & others: acting for the FCA in a ‘land banking’ dispute involving over 500 investors in ten subject schemes.
• Defending a conspiracy claim for in excess of £10m brought by the administrators of a now defunct bank, against a senior partner of a well-known international wealth management group. Settled on confidential terms subsequent to the making of a strike out application.
• Barclays Bank plc v Ball & Clarke: an appeal concerning advice given by a leading firm of accountants, and statements allegedly made by an employee of a leading high street retail bank, in relation to the Enterprise Finance Guarantee Scheme.
• Advising a commercial bank on the enforceability of a series of cross-guarantees and other security valued in excess of £4 million.
• Acting as sole counsel for a leading high street retail bank in a mortgage dispute involving allegations of fraud, undue influence and misrepresentation.
• Defending a claim by a senior Nigerian barrister against a leading high street retail bank concerning allegations of fraud and breach of mandate. Successful settlement after two days cross-examining the claimant.

Tom has considerable expertise in Chancery litigation and Chancery-related professional negligence claims.

Examples of his recent work in this area include:

• Defending a claim against the former administrator of a company under para 75 of Sch B1 arising out of a pre-pack sale of assets and book debts at an alleged substantial undervalue.
• A claim against the administrator of a series of pensions schemes arising out of the alleged negligent miscalculation of benefits and overpayment to scheme members.
• Advising the operating company of a major and well-known professional sports league in relation to certain prescribed consequences on the happening of an insolvency event.
• Sharma v Sharma [2014] BCC 73, [2013] EWCA Civ 1287: successfully representing the Respondent in the Court of Appeal, subsequent to a two-week High Court trial [2012] EWHC 2529 (Fam) relating to the ownership of a multi-million-pound dental business and associated allegations of breach of fiduciary duty and diversion of corporate opportunities.
• Bristol Alliance (No 1) Ltd & others v Bennett & Cadwallader [2013] EWCA Civ 1626: an appeal to the Court of Appeal concerning the entitlement of various parties to funds in excess of £0.5 million held in escrow by a landlord (2013).
• Financial Conduct Authority v Cavendish Moore Ltd & others: acting for the FCA in a ‘land banking’ dispute involving over 500 investors in ten subject schemes.

Tom has experience of IT-related disputes (both as sole and junior counsel). Recent cases include:

• Acting for a reseller of telecommunication services in a substantial breach of contract claim (worth c.£6m) for failure to pay sums due in respect of the purchase of a large customer base and consequential losses.
• Successfully defending a claim brought by an IT services company for services allegedly provided to a major IT company in Sweden, subsequent to a three-day trial. Trial judge remarked on his “neat cross-examination” of the Claimant’s key witness.
• A claim against a leading firm of IT consultants relating to a Payment Card Industry Data Security Standard audit of a company which provided online real-time booking facilities for the UK tourist industry.
• Defending a claim by solicitors against an IT services company for alleged mis-selling of volume licences and loss/corruption of data.
• Defending a claim by an IT consultant in relation to the implementation of a well-known e-commerce software solution.
• Advising a major software developer in relation to a dispute arising out of a multi-billion-pound government contract. Settled under confidential terms.

4 New Square maintains a very strong Sports practice and continues to be widely recognised and regarded for offering expertise in the field of Sports law – both in the sub-specialities of sports disciplinary law and commercial sporting disputes. Tom is willing to consider instructions on a pro bono basis where appropriate.

Recent cases include:

• Defending a semi-professional rugby player in proceedings before the NADP relating to the alleged use of anabolic steroids (2017).
• Successfully defending a claim brought by a well-known bloodstock auctioneer relating to the sale of a racehorse (instructed as sole counsel). Three-day multi-track trial involving multiple claims and defendants (2015).
• Advising the operating company of a major and well-known professional sports league in relation to certain prescribed consequences on the happening of an insolvency event (2015).
• Acting for the former agent of a well-known professional footballer in a $2.5 million claim relating to the exploitation of the player’s image rights and connected claims for inducing breach of contract and conspiracy (2014).