In 1993 Stevens became the youngest jockey to win $100 million in career prize money. Riding Thunder Gultch, he won both the Kentucky Derby and the Belmont Stakes in 1995. Two years later, aboard Silver Charm, he captured his third Kentucky Derby and his first Preakness.
In 1998 he and Victory Gallop ended Real Quiet’s bid for the Triple Crown by winning the Belmont. Stevens’s success continued in 2001 when he rode Point Given to a series of victories, most notably the Belmont and the Preakness. Stevens also raced in England and France, and arguably his most-notable win abroad was the 1999 Duke of Edinburgh Stakes at the British Royal Ascot.
In 2005 Stevens retired, and he subsequently worked as a racing analyst, a jockey’s agent, and a trainer. He also pursued a career in acting, having already played the part of legendary jockey George Woolf in the 2003 film Seabiscuit. In 2011 Stevens signed on to portray Ronnie Jenkins, a former jockey on the skids on the HBO cable-television series Luck. When the show was canceled after one season, however, Stevens decided to return to racing.
He underwent a strict training regime and changed his overall lifestyle. More important, his right knee, which had undergone 10 different operations since 1999 and had induced him to retire, was stronger and less painful. In 2013, his first year back, Stevens triumphed in the Preakness Stakes, aboard Oxbow. In 2014 he missed several months of the competition after undergoing knee-replacement surgery. He also took some time off from racing after having a hip replaced in late 2016.
Stevens’s memoir, The Perfect Ride, was published in 2002. He was inducted into the Racing Hall of Fame in 1997.
