The odds weren’t in his favor at the Petromalo Mile. Nor has the 2025 season been kind to the 2020 Kentucky Derby-winning jockey. The Triple Crown races had been underwhelming, considering the stature of the jockey, who is revered by most trainers. Yes, it is the trainer who gets most of the credit from the horse racing fans, but it takes an equally good jockey to be a winner. Or sometimes, it’s a skilled jockey who sees it through all the way. Something exactly like the latter unfolded on the Colonial Downs racetrack on August 9.

The name John Velazquez needs no introduction. Be it for being a winner through and through. Or for his controversial side that often lands him in hot water with the racing governing bodies. Pushing the boundaries of the law has always been an issue for the veteran jockey. He has served so many suspensions for either illegal use of a whip or interfering with a competitor. Or in some other way, Velazquez has managed to draw the ire of the officials and the ridicule of the fans.

Nevertheless, he was definitely not expected to win the $100,000 Petromalo Mile Stakes aboard Rolando. But guess what? Velazquez didn’t just win. He and Rolando smashed through the race with a new track record of 1:33.55. And the Racing Hall of Famer later revealed the ebb and flow of emotions during the race.

The three-time Kentucky Derby winner was talking to FanDuel Racing reporter Andie Biancone after the race. In the clip shared on their X handle, Biancone asked the winning jockey if he was worried about going too fast too early, or if he had it under control all the way. “No, I had him in hand the whole time,” Velazquez said. And he continued, “Until I got to the ⅜ th pole, then I finally put my hands down when he was just free, let him get his own momentum.”

Obviously, there were things to worry about for the horse racing legend. It was about pacing the race and conserving energy for the late burst. This was especially the strategy for Rolando because this was his longest race at 1 mile (8 furlongs). The circumstances also put Rolando as only fourth-favorite behind Flood Zone, Barbadian Runner, and Roar of the Beast. But it was a special day for the three-year-old colt. “I was trying to save him for the end, but today it looked like he can go all day.” And that led to the headline win.

Johnnie V didn’t know that a new track record had been made until much later after the race. Talking about it, the 53-year-old jockey went into how they prioritized the speed strategy. “I waited until the 3/16 pole to ask him to do something.” He didn’t even have to resort to any extreme measures, like in the December 2022 Cigar Mile Handicap race at Aqueduct Racetrack. He was suspended for a day and fined $4017. Velazquez was hit with similar suspensions in 2019 and in 2015. This time, however, at the Colonial Downs, it was just different. “l was like, well, I didn’t have to hit him, I just kind of showed him the way to keep his mind in the business, but he was rolling.”

It was a proud moment for the jockey at the Petromalo Mile, given his past. And it was all because of the magic of Rolando, whose connections were full of praise for the Vekoma-sired colt. But for Velazquez, it was all the more glory added to his list of accolades.

The evergreen Johnnie Velazquez and his special place in horse racing

His humble beginnings in Carolina, Puerto Rico, were challenged by Velazquez’s desire to pursue his passion, which was to be a jockey. Not playing it safe, even going against his mother’s wishes for him to become a lawyer or something more sombre and traditional  — no, Johnnie V was a rebel. So, despite not knowing English, he decided to travel to America in 1990, at the age of 18.

The rest, as we know, has been a stellar history of wins, dominance, and skilful authority. The iconic jockey has 6,732 wins under his belt! Yes, you read that correctly. The man has more than 16000 podium place finishes, and he is not even close to slowing down, as has been detailed above. Pun intended, maybe? His career earnings currently read at a mammoth $502 million, give or take.

As far as his accolades go, he is a three-time Kentucky Derby winner, Preakness Stakes winner, and Belmont Stakes Champion each. Add to that two Breeders’ Cup Classic wins, and you realize there is not a track he hasn’t dominated. To be honest, the list is long, and it gets more impressive with every addition.

This horseracing luminary deserves even more acknowledgment for his greatness. He was named a two-time back-to-back Eclipse Award winner as the most outstanding jockey in North America. Whichever horse he saddles at the 2025 Breeders’ Cup Classic becomes one of the favorites because the field will be stacked. Will Velazquez repeat his victorious ways? We hope so.