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 over three decades, has faced a turbulent year marked by financial strife. Yet, with his characteristic resilience, Dettori is setting his sights on a triumphant return to Royal Ascot, the prestigious British racing event where he has claimed 81 victories and topped the jockey standings seven times. Despite filing for bankruptcy in March 2025, Dettori’s passion for the sport and his unyielding spirit are driving him to reclaim his place on one of racing’s grandest 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 rode all seven winners on a single card at Ascot, a feat that cost bookmakers an estimated £40 million. With over 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 dismount, a celebratory leap from the saddle, became 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 prolonged dispute with HM Revenue and Customs (HMRC) over a tax avoidance scheme. The issue surfaced in December 2024 when a court lifted his anonymity, revealing his financial troubles. In a candid statement, Dettori expressed his regret: “I am saddened and embarrassed by this outcome and would advise others to take a stronger rein over 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 be drawing a line on this long-term matter, which enables me to reset and focus on my international riding career.”

The bankruptcy filing stemmed from a tax structure Dettori claimed was approved by HMRC but later challenged. He dismissed his former advisors, acknowledging the mess they had left him in. Estimates suggest Dettori earned between £15 million and £20 million from racing alone, with career earnings nearing £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 measures. Tax expert Dan Neidle, commenting on the case, remarked 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.”

Despite these challenges, Dettori’s focus remains on racing. After leaving Britain in 2023, he reversed his retirement plans and relocated to the United States, first to California and later to Florida. His move has proven fruitful, with 21 wins in 2025, including a £1 million victory aboard Raging Torrent in the Metropolitan Handicap at Saratoga. This success has 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 do have the little devil on my shoulder that says to me ‘one more time,’” Dettori shared in a blog for a betting site. “I did get some offers but I am not going to lie, I do miss it. I had over 80 winners, it has been a huge part of my life.”

Dettori’s connection to Royal Ascot is profound. His 81 victories include memorable moments like his 2023 Coronation Stakes win aboard Inspiral, which he described as a career highlight. In a recent interview with ITV Racing, he reflected on his return: “I’m good, 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 how I missed it so much. Never say never.” His words capture a mix of nostalgia and determination, hinting at a potential comeback that has fans buzzing with anticipation.

The prospect of Dettori riding at Royal Ascot again is a tantalizing one. He has already shared his insights for the 2025 meeting, tipping horses like Zarigana for the Coronation Stakes and Inisherin for the Queen Elizabeth II Jubilee Stakes. He also backed young jockey Billy Loughnane’s mount, 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, underscores his deep understanding of the sport and the Ascot track.

Dettori’s story is one of resilience in the face of adversity. His bankruptcy, while a public embarrassment, has not dimmed his competitive fire. The jockey’s move to the U.S. 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 will be there this year,” he said, noting plans to visit for his daughter’s birthday and to reconnect with old friends. “It’s nice to be here and it’s amazing racing through the week.”

For fans, Dettori’s potential return to racing at Ascot is more than just a comeback; it’s a chance to witness 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 makes him a compelling figure. The tax dispute and bankruptcy may have tarnished his financial standing, but they have not eroded his passion or his legacy.

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