From Millionaire to Bankrupt: The Fall of Frankie Dettori de Grace

Lanfranco “Frankie” Dettori, the charismatic Italian jockey whose name has become synonymous with horse racing, faced a dramatic fall from financial prosperity to bankruptcy, a story that shocked the sporting world. Once celebrated for his unprecedented success, including riding all seven winners at Ascot in 1996, Dettori’s journey from an estimated net worth of £15 million to £20 million to financial ruin is a cautionary tale of mismanagement, misfortune, and personal loss. The recent revelation that Dettori won £1.8 million in the lottery only to lose it all, coupled with the sudden death of his close friend, has cast a shadow over his 38-year career, raising questions about his future as he contemplates retirement.

Dettori’s career began in Milan, where he was born in 1970 into a family steeped in racing heritage. His father, Gianfranco Dettori, was a renowned trainer, giving young Frankie early exposure to the sport. At 14, he moved to Newmarket, England, to work as a stable boy, eventually rising to become a jockey for Godolphin Racing. Over the decades, Dettori amassed more than 3,350 wins, including 287 Group 1 races and 23 British Classics. His flamboyant personality and signature flying disc made him a global icon, raising the profile of horse racing. Beyond the track, Dettori ventured into entertainment, appearing on shows like I’m a Celebrity… Get Me Out of Here! and A Question of Sport and launched business ventures, including a chain of Italian restaurants and a line of frozen pizzas. These efforts, combined with endorsement deals, significantly increased his wealth, with estimates suggesting he earned £3 million to £5 million a year at his peak.

The turning point in Dettori’s financial saga came with a £1.8 million win, a windfall that could have secured his future. However, like many lottery winners, Dettori fell victim to reckless spending and poor financial decisions. Reports suggest he splurged on luxury cars, lavish vacations, and generous gifts for family and friends, mirroring the stories of other winners like Michael Carroll, who squandered £9.7 million, and Sharon Tirabassi, who lost $10.5 million over a decade. Dettori’s lottery fortunes quickly declined, exacerbated by his involvement in a controversial tax evasion scheme. In December 2024, his financial troubles became public when a High Court judge rejected his plea for anonymity in a dispute with HM Revenue & Customs (HMRC). The scheme, allegedly designed by discredited advisor Paul Baxendale-Walker, led to a significant tax liability that Dettori was unable to resolve, forcing him to file for bankruptcy in March 2025.

In a statement, Dettori expressed his deep regret, saying, “I am saddened and embarrassed by this outcome and would advise others to reinstate stronger in their financial matters.” The bankruptcy filing, a major blow to his legacy, may force him to liquidate assets, including his lavish properties, to settle debts. The financial strain was compounded by a personal tragedy. In August 2025, Dettori’s close friend Duncan died unexpectedly in Dubai, a loss that left the jockey reeling. “Two weeks ago, I was thinking about quitting when I lost my best friend,” Dettori shared after securing a victory at Kentucky Downs in Duncan. This emotional turmoil fueled speculation about his retirement, despite his earlier decision to continue racing in the United States after reversing his retirement plans in 2023.

Now 54 and based in Florida, Dettori’s career continues, but with reduced success compared to his British heyday. In 2025, he rode 11 winners, earning just under £800,000, a far cry from his 2024 earnings of $13 million. His move to the US was meant to pursue new opportunities, including a coveted Kentucky Derby victory, but bankruptcy and personal loss have focused on his uncertain future. The jockey’s resilience has been tested before—in a plane crash, overcoming a cocaine ban, and battling depression—but this chapter presents a formidable challenge.

Dettori’s story underscores broader lessons about wealth management. Like many high-profile figures, from lottery winners to athletes, his reliance on advisors led to catastrophic consequences. The racing community and fans continue to rally behind him, hoping his talent and charisma will pave the way for a comeback. For now, Dettori remains focused on his international career, determined to rebuild. Yet his journey from millionaire to bankrupt serves as a stark reminder that even the most famous figures are not immune to financial and personal pitfalls.