From Millionaire to Bankrupt: Frankie Dettori’s Fall from Grace

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

Dettori’s career began in Milan, where he was born in 1970 to a family steeped in racing heritage. His father, Gianfranco Dettori, was a renowned trainer, providing young Frankie with early exposure to the sport. At 14, he moved to Newmarket, England, to work as a stable lad, eventually rising to prominence as a jockey for Godolphin Racing. Over the decades, Dettori amassed over 3,350 victories, including 287 Group 1 races and 23 British Classics. His flamboyant personality and signature flying dismount made him a global icon, elevating horse racing’s profile. 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 endeavors, combined with endorsement deals, significantly boosted his wealth, with estimates suggesting he earned £3-5 million annually at his peak.

The turning point in Dettori’s financial saga came with a £1.8 million lottery 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 tales of other winners like Michael Carroll, who squandered £9.7 million, and Sharon Tirabassi, who lost $10.5 million in a decade. Dettori’s lottery fortune quickly dwindled, exacerbated by his involvement in a controversial tax avoidance 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 devised by discredited advisor Paul Baxendale-Walker, led to a significant tax liability that Dettori could not resolve, forcing him to file for bankruptcy in March 2025.

In a statement, Dettori expressed deep regret, saying, “I am saddened and embarrassed by this outcome and would advise others to take a stronger rein over their financial matters.” The bankruptcy filing, a major blow to his legacy, may require him to liquidate assets, including his lavish properties, to settle debts. The financial strain has been compounded by 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 of quitting when I lost my best friend,” Dettori shared after dedicating a victory at Kentucky Downs to Duncan. This emotional turmoil has fueled speculation about his retirement, despite his earlier decision to continue racing in the United States after reversing his 2023 retirement plans.

Now 54 and based in Florida, Dettori’s career continues, albeit 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 U.S. was meant to chase new opportunities, including a coveted Kentucky Derby win, but the bankruptcy and personal loss have shifted focus to his uncertain future. The jockey’s resilience has been tested before—surviving 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 trust in advisors led to catastrophic consequences. The racing community and fans continue to rally behind him, hopeful that 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 celebrated figures are not immune to financial and personal pitfalls.