Jockey Stewart Elliott is nearing a rare milestone of 5,000 victories, but it is just one of those wins that defines his career – the Kentucky Derby. Elliott captured the classic in 2004 with Smarty Jones. It’s been the most significant of the 4,983 races he’s won from 32,101 mounts through Sunday, and he said it’s also paved the way for more special moments in racing. “The whole ride with Smarty Jones, it really kind of brought everything to the top,” said Elliott, 55. Elliott also won the Preakness with Smarty Jones and the same year captured the Grade 1 De Francis Dash with Wildcat Heir and the Grade 2 Remsen with Rockport Harbor. He also picked up an ESPY award from ESPN. Elliott later was honored with the George Woolf Memorial Jockey Award at Santa Anita and was inducted into the Canadian Horse Racing Hall of Fame. :: Want to get your Past Performances for free? Click to learn more. Elliott is a native of Toronto. A career in racing seemed inevitable as both sides of his family is steeped in the sport. “My father was a jockey,” Elliott said. “I was born in Toronto, lived there until I was 7. My father, he was having a hard time with his weight, so we went to Hong Kong because my uncle – his brother – was riding over there and the weights were higher. I was over there from 7 to 12.” The family then moved to the East Coast, where Elliott’s father, Dennis, launched his training career. Elliott’s mother, Myhill, comes from a long line of trainers. She gave her son riding lessons. “I started riding show horses when I was 12, 13,” Elliott said. “My sister and I rode Quarter Horses in the shows and then I used to get on horses on the training track before I would go to school.” Elliott’s first win came Jan. 31, 1981, at the Keystone Racetrack, later known as Philadelphia Park, and now Parx Racing. It would be over the same oval he would land the mount on Smarty Jones. Elliott rode the horse throughout his 8-for-9 career, first climbing aboard the John Servis trainee on Nov. 9, 2003, for a maiden special weight sprint at Philadelphia Park. “I had worked a lot of horses for John, but never had worked this horse,” Elliott said. “He breaks on the lead and I thought I was going too fast, thinking, ‘He’s not relaxing. He’s going to stop. There’s no way this horse keeps running like this.’ But he did. “We knew if we could get the horse to settle down and stretch out, that could make him. We were able to do that with him. He was very talented, of course, and I think what helped him, too, was he was never defeated [in his first eight starts]. He thought he was unbeatable.” Smarty Jones won the Pennsylvania Nursery in his second start Nov. 22 at Philadelphia Park. The horse opened his 3-year-old season with a win in the Count Fleet at Aqueduct before sweeping Oaklawn’s series of preps, highlighted by the Arkansas Derby, and going off as the 4-1 favorite in the Kentucky Derby. “It was a monsoon that day,” Elliott said. “The race was held up and everything. He’d never been in the [slop] and I didn’t know how he was going to do, but it never bothered him.” Smarty Jones was a 2 3/4-length winner, making for an unforgettable space in time for Elliott. “It’s unexplainable,” he said. “That’s all I can say.” Elliott has spent the bulk of his career on the East Coast, but Smarty Jones introduced him to Oaklawn and he was a regular at this year’s meet after riding the Remington Park meet in 2019. He has remained in the region and is now vying for the title at Lone Star Park. Elliott will be aboard favorites in three of the track’s four restricted stakes Wednesday, beginning with Direct Dial in the $75,000 Wayne Hanks Memorial. The pair is coming off a five-length win in last month’s Spirit of Texas. “He won very easily,” Elliott said. “He’s a nice horse.” Steve Asmussen trains Direct Dial and also has put Elliott on the 2-year-olds Island Sun and Great Affection in divisions of the Texas Stallion Stakes. “Steve Asmussen’s young horses, he has them ready,” Elliott said. “His 2-year-olds, they have ability, and they’re prepared.” Elliott, whose 216 stakes wins include victories with Jostle and Round Pond, plans to remain in the saddle for the foreseeable future. To date, his mounts have earned $105 million. “As long as I feel like my ability is still there and the business is good, I’ll ride it out, see how far we go,” said Elliott. Before long, it will be a milestone of 5,000 wins.