It was the moment Frankie Dettori fell prey to the “Streisand effect”.
“The big tax mystery of 2024,” began an X post by Dan Neidle in January last year, to which was attached a legal judgment in a case between HM Revenue & Customs and a man described only as the “taxpayer”.
An audacious attempt by this “taxpayer” to conceal his identity prompted Neidle, founder of Tax Policy Associates (TPA), to sound the alarm in a message since viewed 1.8 million times. Almost nine months later, Dettori was outed as the man in question when his application for “permanent anonymity” – over what transpired to be a long tax-avoidance battle with HMRC – was thrown out by the Upper Tribunal Tax and Chancery Chamber.
Dettori’s doomed attempt to keep this battle secret, culminating in him filing for bankruptcy last month, has become a prime example of a phenomenon popularised following a failed 2003 lawsuit by Barbra Streisand. The singer had tried to get a photograph depicting her home removed from the internet, only for a picture almost no one had seen to end up being viewed hundreds of thousands of times.
That Dettori went bust following his own brush with the Streisand effect is one of many ironies of last month’s descent into financial ruin for the 54-year-old, who over nearly four decades of flying dismounts and flamboyance in and out of the saddle became one of the world’s most famous jockeys. Indeed, the Italian’s roller-coaster career had already featured three Flat Jockeys Championships, more than 3,500 winners – 50-plus of them for Queen Elizabeth II – a stint as captain on A Question of Sport, entries into Celebrity Big Brother and I’m a Celebrity… Get Me Out of Here!, a six-month racing ban for taking cocaine, and a plane crash he was lucky to survive. All topped, of course, by one of sport’s great miracles: his 25,000-1 “Magnificent Seven” victories at Ascot in 1996.
Arguably the biggest irony of all from Dettori’s sad descent into bankruptcy is that his outing in December left more questions than answers about how it all went wrong for someone whose success enabled him to amass an estimated £18 million fortune. The tribunal judgment that threw out his “permanent anonymity” application followed a number of hearings and decisions in a case dating back years. But, despite ruling against him, the same tribunal refused to grant access to documents and transcripts from previous proceedings into a tax-avoidance case the First-tier Tribunal Tax Chamber had ruled should be held in private. Justice Miles and Judge Thomas Scott did permit reporting of the contents of documents included in a bundle of evidence submitted for the most-recent Upper Tribunal proceedings. These feature few details about Dettori’s tax affairs and the payments he had allegedly dodged, but the documents – seen by Telegraph Sport – nevertheless contain clues as to how he ended up going bust.
They reveal that what Dettori in December described as “the mess that I have been put in” actually dates back at least to 2012, the year he was banned from racing after testing positive for cocaine use. The documents also show that, according to HMRC, he was involved over a five-year period in “the same tax-avoidance scheme” used by a dentist it had been pursuing for almost £1 million in income tax and National Insurance payments. The documents describe an appeal by this dentist, Mark Northwood, against a demand for the money as one of two “lead cases” in an HMRC crackdown on that scheme.
Not being a celebrity, Northwood did not apply for anonymity in his case, a judgment on which was published two years ago. It laid bare how the scheme he used worked. There were references to tax havens Belize and the Channel Islands and a chronicle of how Northwood paid money into a “remuneration trust”, which returned it to him in the form of loans to prevent it becoming subject to income tax or National Insurance. A damning judgment found these loans did anything but absolve him of liability for such contributions and branded documentation connected with the scheme “a sham”.
It also revealed who lay behind that scheme: a man named Paul Baxendale-Walker.
Baxendale-Walker is described by TPA as “probably the UK’s most notorious tax avoidance scheme promoter” but that description only covers a small part of an extraordinary life and career even more colourful than Dettori’s. Now going by the name Paul Chaplin, Baxendale-Walker worked as both a barrister and soft-porn entrepreneur (even starring in erotic films) before being struck off as a solicitor over advice he had provided to clients over his own tax schemes.
He went on to buy the “lads’ mag” Loaded and Paul Raymond Publications, which included adult magazines Mayfair and Men Only, whilst enjoying the company of a string of women he called his “hunny bunnies”. In 2012, he appeared to tire of his playboy lifestyle and underwent several months of therapy for sex addiction and is now described on his own website as a “psychologist, healer, researcher”.
But he has been unable to escape his past and, in 2016, he was fined after pleading guilty to forgery by impersonating an HMRC official years earlier. In 2017, his eponymous law firm was found by the Supreme Court to have “devised and operated” a tax-avoidance scheme that contributed to Rangers going bust in 2012. Having himself been made insolvent in 2018 following a £16.7 million negligence claim from a former client, he was subject to a 10-year bankruptcy restrictions order two years later after a court was told he attempted to hide his assets and failed to make a “full and frank disclosure of his affairs”.
The judgment in the Northwood case features an account by the dentist of an alleged 2009 meeting with Baxendale-Walker, who he said “talked about remuneration trust structures” and told him they “had been used for many years unchallenged by HMRC, who were fully aware of them” and “were outside DOTAS (Disclosure of Tax Avoidance Schemes) procedures”.
There were echoes of Northwood’s testimony in a statement issued by Dettori in December after he lost his anonymity battle. He said: “A few years ago, I employed the services of professional specialist tax advisers to look after mine and my family’s financial affairs. A structure was created and I was told that it had been approved by HMRC.” Dettori added that his “former advisers” had since been dismissed but did not identify them. It was a similar story when he announced he was filing for bankruptcy, despite saying he was “saddened and embarrassed by this outcome and would advise others to take a stronger rein over their financial matters”.
Adding further intrigue to the whole affair is that Dettori used the same firm of solicitors, Morr & Co, in his anonymity application as that which Baxendale-Walker used in 2023 to escape a £14 million penalty imposed by HMRC over a demand for him to supply it with certain information. It is unclear exactly when Morr & Co began representing Dettori in his battle with HMRC, which documents show pre-dates the coronavirus pandemic.
He managed to maintain total secrecy about his tax-avoidance case for what appears at least five years, which took in a number of tribunal hearings and decisions and hundreds of pages of legal submissions. There was even a point almost three years ago when, according to a submission by HMRC to the most recent tribunal proceedings, Dettori rejected an offer that would have allowed him to retain his anonymity. That was after the First-tier Tribunal had directed in September 2021 that “preliminary proceedings in this matter shall be heard in private”.
All this was going on behind closed doors amid no small drama in Dettori’s public life. After a racing career that began in the 1980s, he announced his retirement in December 2022. Days before what was meant to be his October 2023 farewell at Ascot – the scene of his greatest triumph – he duly performed an about-turn and revealed plans to relocate to California and continue riding there. Not that it prevented him receiving a rousing send-off after a fairy-tale double, including an inspired last-to-first victory on King Of Steel in the Champion Stakes in his final race on British soil.
“Oh, Frankie Dettori. Oh, Frankie Dettori,” came the chants from the grandstands to the tune of The White Stripes’ Seven Nation Army. “Unreal. Crazy. Nuts. Incredible. Hollywood stuff,” gushed the man about to relocate to Tinsel Town. To cap it all, the Queen unveiled a statue of Dettori by Ascot’s Grandstand Lawn that same day.
Barely a month later – as Dettori was preparing to enter the I’m A Celebrity jungle – the fateful hearing took place that would eventually lead to his legacy in Britain cast to be in a different light. The published January 2024 judgment which followed that hearing came to the attention of Neidle after the Upper Tribunal found there had been “material errors of law” in the First-tier Tribunal’s September 2021 decision to grant Dettori anonymity. The ruling said he had obtained the benefit of privacy despite failing to produce “any evidence of harm or prejudice”, something that risked “a blanket derogation from open justice by the back door”. Before he could be named, Dettori sought permission to appeal, ultimately triggering fresh Upper Tribunal proceedings in October.
He also withdrew his “substantive appeal” over HMRC’s pursuit of him for unpaid taxes, leaving him liable for that money, come what may. After Neidle publicised the case, TPA and media including the Press Association, The Times and The Sun joined forces with HMRC to oppose his latest anonymity application. A judgment throwing out that application followed in November and – after a deadline for appealing that expired – he was named on December 9.
On what happened between then and his shock announcement on March 13 that he was filing for bankruptcy, Dettori has said very little. His statement that day said he had been “working with HMRC in an attempt to find a solution to my financial situation”.
He also said: “Bankruptcy is a major decision and its consequences will affect me for many years. I am relieved to be drawing a line on this long-term matter, which enables me to reset and focus on my international riding career.”
‘Amazing they thought it a good idea to buy this scheme’
Dettori declined to respond to questions about the documents seen by Telegraph Sport, whether he had ever met or spoken to Baxendale-Walker, and why the pair had both employed the same law firm. That was after Neidle wrote on X: “Amazing that Dettori/his advisers thought it was a good idea to buy a scheme from a struck-off solicitor and convicted fraudster who gave negligent advice and then went bankrupt.”
Dettori also declined to comment on how much he owed HMRC when he went bankrupt. Neidle told Telegraph Sport it was likely to run into “hundreds of thousands or millions”, on top of a probably six-figure bill in legal costs the jockey would have amassed during his various appeals. Neidle also said that for someone as wealthy as Dettori to use the kind of tax-avoidance scheme linked to Baxendale-Walker would be “really unusual because people like that normally have proper advisers”. An HMRC spokesman said: “We take a supportive approach to dealing with customers who have tax debts and do everything we can to help those who engage with us to get out of debt, such as offering instalment plans.”
Dettori, who relocated from California to Florida in February, has been back racing – and winning – since his bankruptcy was confirmed on March 17. According to the Insolvency Service Register, he will be automatically discharged on the same date next year. With the trustee of his bankruptcy certain to closely examine his assets and future income to see if they can be used to pay HMRC and any other creditors, the full impact of going bust on Dettori remains to be seen.
