John Velazquez has become the first jockey in history to top $500 million in career earnings, a mark that now stands at more than $519.7 million as he heads into another Kentucky Derby week riding Further Ado. The 3-time Kentucky Derby winner said he does not spend much time thinking about the numbers.
“I don’t, actually – I never think about it!” Velazquez said. He added that he is “still here, still riding, still enjoying it,” and called himself “very blessed” to have the job, saying the results have come from preparation rather than obsession with purses. In 2026, he has already earned $6.1 million.
The National Museum of Racing and Hall of Fame says Velazquez holds the North American record for the highest career earnings by a jockey, a status that places the Puerto Rico native, who now lives in New York, among the most accomplished riders in the sport. He is also a 2-time Belmont Stakes winner and has won the Preakness Stakes, a résumé that helps explain why his earnings milestone carries more weight than a simple number.
Velazquez credited his wife, Leona O’Brien, for helping him stay in the game. “My wife understands the life as she was born and raised in racing. Jockeys travel a lot and miss a lot, so not having a partner behind you, supporting what you do, it wouldn’t work. I’m very blessed to have that,” he said. Ahead of the Kentucky Derby, the pair was also recognized with the Marylou Whitney and John Hendrickson Award from the New York Race Track Chaplaincy for their longstanding commitment to the backstretch community at Saratoga Race Course, Belmont Park and Aqueduct Racetrack.
That support for the backside is part of the same racing world that shaped O’Brien, and Velazquez said both of them were “extremely honored and grateful” to be recognized. He also pointed to the stable staff who keep the sport moving, saying that anyone who spends time at a racetrack knows they are “the unsung heroes” of racing.
As for Further Ado, Velazquez said he has been following the horse since he broke his maiden at Keeneland on April 25, when he was surprised by how easily the colt won. “I was right next to him,” he said of that race, recalling how the horse swept past him and left him stunned by the margin. He said he has been watching Further Ado ever since and now has the chance to ride him in the Derby.
The milestone matters because Velazquez is not just any veteran still collecting purses. He is a leading figure in American racing whose record earnings, classic wins and continued presence in the saddle have made him one of the defining jockeys of his era. What comes next is simpler and more immediate: Further Ado goes to the Derby with one of the most successful riders in the sport aboard, and Velazquez gets another chance to add to a career he says he is still enjoying, even if he never keeps track of the totals.