In the world of horse racing, few names shine as brightly as Frankie Dettori. The 54-year-old Italian jockey, a legend whose career spans three decades, has faced a turbulent year marked by financial strife. Yet, with his characteristic resilience, Dettori is aiming for a triumphant return to Royal Ascot, the prestigious British racing event where he has won 81 times and topped the jockey rankings seven times. Despite filing for bankruptcy in March 2025, Dettori’s passion for the sport and his unyielding spirit drive him to reclaim his place on one of racing’s biggest stages.

Dettori’s journey to this moment has been nothing short of cinematic. Born in Milan, he burst onto the scene in 1987, winning his first race at Goodwood. His career skyrocketed with the historic ‘Magnificent Seven’ in 1996, when he made all seven of his winners on a single card at Ascot, a feat that cost bookmakers an estimated £40 million. With more than 3,500 career wins, including 287 Group 1 races and 23 British Classics, Dettori has cemented his status as one of the greatest Flat jockeys in history. His signature flying Dismound, a bum-jump from the saddle, has become a symbol of his charisma and connection with fans.

However, 2025 brought unexpected challenges. In March, Dettori announced he was filing for bankruptcy after a protracted dispute with HM Revenue and Customs (HMRC) over a tax avoidance scheme. The issue surfaced in December 2024 when a tribunal lifted his anonymity, revealing his financial troubles. In a frank statement, Dettori expressed his regret: “I am saddened and embarrassed by this outcome and would advise others to reinstate stronger on their financial matters. Bankruptcy is a major decision and its consequences will affect me for many years.” Despite the setback, he added: “I am relieved to draw a line under this long-term issue, allowing me to reset and focus on my international driving career.”

The bankruptcy filing resulted from a tax structure that Dettori claimed was approved by HMRC but later disputed. He dismissed his former advisors, acknowledging the mess they had left him in. Estimates suggest Dettori earned between £15 million and £20 million from the race, with career profits close to £160 million. Yet the financial burden, potentially involving hundreds of thousands or even millions in unpaid taxes and legal fees, forced him to take drastic action. Tax expert Dan Neidle, commenting on the case, remarked on X: “Unbelievable that Dettori/his advisors thought it was a good idea to buy a scheme from a convicted solicitor and fraudster who gave negligent advice and then went bankrupt.”

Despite these challenges, Dettori remains focused on racing. After leaving Britain in 2023, he reversed his retirement plans and moved to the United States, first to California and later to Florida. His move proved successful, with 21 wins in 2025, including a £1 million victory aboard Torrent Rage in the Metropolitan Handicap at Saratoga. This success fueled his ambition to return to Royal Ascot, a venue he describes as a cornerstone of his career. “I won’t lie to you, I have the little devil on my shoulder saying ‘one more time,’” Dettori explained in a blog for a betting site. “I’ve had offers, but I’m not going to lie, I miss it. I’ve had over 80 winners; it’s been a big part of my life.”

Dettori’s connection with Royal Ascot runs deep. His 81 wins include memorable moments like his 2023 Coronation Stakes win aboard the inspirational, which he described as a career highlight. In a recent interview with ITV Racing, he reflected on his return: “I’m doing well, I flew here on Sunday after riding in Kentucky, it’s my daughter’s birthday, you know I love Royal Ascot. When I was driving here, I was thinking about how I missed it so much. Don’t say never.” His words capture a mix of nostalgia and determination, hinting at a potential return that has fans buzzing with anticipation.

The prospect of Dettori riding at Royal Ascot is once again tantalizing. He has already shared his ideas for the 2025 meeting, tipping horses like Zarigana for the Coronation Stakes and Inisherin for the Queen Elizabeth II Jubilee Stakes. He has also backed young jockey Billy Loughnane, Oliver Show, as a Longshot in the Royal Hunt Cup, and Willie Mullins as a Banker in non-Group 1 races. His expertise, even as a spectator, underlines his deep understanding of the sport and the Ascot track.

Dettori’s story is one of resilience in the face of adversity. His bankruptcy, despite the public embarrassment, hasn’t dimmed his competitive fire. The jockey’s move to the United States and his continued success there demonstrate his ability to adapt and thrive. His return to Royal Ascot, even if not in the saddle this year, marks a symbolic homecoming. “I’ll be here this year,” he said, noting plans to visit his daughter’s birthday and reconnect with old friends. “It’s nice to be here, and it’s an incredible race during the week.”

For fans, Dettori’s potential return to racing at Ascot is more than just a return; it’s a chance to see a living legend defy the odds. His career has been defined by moments of brilliance, from his Ascot heroics to his three champion jockey titles. Yet it’s his ability to rise above personal and professional challenges that make him a compelling figure. The tax dispute and bankruptcy may have tarnished his financial standing, but they haven’t eroded his passion or his legacy.

As Royal Ascot 2025 approaches, the racing world is watching closely. Will Dettori once again take to the saddle, performing his iconic flying abandon in the Berkshire sunshine? His own words suggest the possibility: “Never say never.” For a man who has turned unlikely chances into historic triumphs, another Ascot chapter feels not only possible, but almost inevitable. Whether he’s riding or simply soaking up the atmosphere, Frankie Dettori’s presence at Royal Ascot will remind fans why he remains the sport’s most enduring icon.