Only one thing nagged at the man known around the thoroughbred racing world as Johnny V.
"I would feel terrible if I retired and never won a Derby for Todd," he told Cordero.
Todd is Todd Pletcher, the trainer whose own brilliant career has been inextricably linked to Velazquez. The pair has won more than 1,600 races together in a working bond that hearkens back to the days when each major American stable seemed to have a house rider.
"It's very rare to have the same relationship that spans 20 years or 25 years," said Hall of Fame jockey and NBC analyst Jerry Bailey. "Because trainers and jockeys go hot and cold. They both have to make livings independent of each other and when one goes cold, the rule is they'll usually drift to somebody else. But both of these guys have been tremendously successful all along the way, feeding off each other."
For all their success together, however, Pletcher and Velazquez had never teamed up to win the Derby. Each had won the race once, Pletcher putting Calvin Borel aboard Super Saver in 2010 and Velazquez riding Animal Kingdom for Graham Motion the next year. But their disconnect in Derby timing seemed almost cruel.
At least until May 6, when Velazquez guided Always Dreaming on a perfect trip over the slop at Churchill Downs.
Now, the most enduring trainer-jockey duo in the sport will try to capture the Preakness, a race neither man has won. If Always Dreaming leaps that hurdle, Pletcher and Velazquez will head home to New York for their first shot at a Triple Crown.
Pletcher credits Velazquez as one of the foundational elements in his rapid rise to the top of the training world.
"As our stable grew, our relationship grew at the same time," he said. "We were winning races together, and it was working out so well that I didn't need to reach out to many other jockeys. For a trainer, when your operation grows and you don't have to worry about who's going to ride this one and who's going to ride that one, if you have a go-to guy who's going to ride most of them, it makes my job easier. Especially when it's someone as talented as Johnny."
The reverse equation is equally true, Cordero said. Velazquez, one of the kindest people in racing by all accounts, might not have soared to a Hall of Fame career if Pletcher had not put him on so many gifted horses.
"It's been the major thing behind Johnny's big success," said Cordero, a Hall of Fame jockey in his own right.
Velazquez had won 1,621 races for Pletcher going into Friday, more than 1/3 of the trainer's career total and more than 1/4 of the jockey's. If you only count the $137,966,765 they've won together, the sum would make Pletcher eighth in history in career earnings.
"It's a long time for him to still trust in me and give me the opportunity," Velazquez said. "It's not very often it happens in this business."
Pletcher's old boss, D. Wayne Lukas, marvels at the bond between his former assistant and Velazquez. Lukas had his favorite jockeys, including Cordero, but never a house rider.
"I always tell the agents we're going to date but not get married," he joked.
Lukas called Pletcher-Velazquez "a unique relationship and a great one." He'd have liked to put Velazquez on more of his own horses.
"The problem with Johnny and me is I loved Johnny's riding, I love him as a person. He's a class act," Lukas said. "But Todd's stable and my stable clashed all the time. So every time I looked up and wanted Johnny, Todd had one in there so I'd get bounced."
Velazquez, 45, went to jockey school in his native Puerto Rico and was building his career there when Cordero, the greatest of all Puerto Rican riders, heard about him from an agent friend.
Cordero was skeptical about the teenager, who did not speak English and did not come from a family of riders. His friend sent film of the sweet-natured kid.
"To be honest, I wasn't impressed at all," Cordero recalled.
But Dick Allen, the baseball star and avid racing lover, happened to stop by his house while he was watching Velazquez.
"You know, brother, he reminds me of you," Allen told Cordero.
So Velazquez moved to New York and bunked on Cordero's couch while Allen helped him get his career going. He learned English watching "The Little Mermaid" with Cordero's daughter.
Cordero urged his wife, who trained horses, to give the young Velazquez a mount. He won his first race for her.
The next time she ran an intriguing horse, she said, "I think I'm going to put Johnny on him."
"What about me?" said Cordero, who was still riding at the time.
The next great Puerto Rican jockey was on his way.
Pletcher, meanwhile, was learning how to operate a sprawling, industry-leading barn as an assistant to Hall of Fame trainer Lukas.
Cordero had ridden for Lukas and knew Pletcher through that connection.
He recalls walking into the young trainer's barn one day and saying: "Todd, I have a jockey who's going to be a champion. I know you're going to be a champion. You should team up together."
Velazquez said the relationship has endured because Pletcher is both brutally honest and graceful in defeat.
"He's not a guy who's going to come screaming at you when you don't win a race," Cordero said. "He doesn't hold grudges, and he doesn't have a single mean thing about him."
If Pletcher doesn't believe his horse can win a given race, he'll sometimes tell Velazquez to switch to a more promising mount for another trainer.
They like and trust each other that much.
Velazquez was essential in creating a house style for Pletcher's vast operation, one that emphasizes stalking the lead closely, as Always Dreaming did so ably in the Derby.
"I think because Johnny is naturally a position rider … and Todd's horses are such that they have a certain amount of early speed and you can position them, it works hand in hand," Bailey said.
Velazquez generally got first crack at picking a mount among Pletcher's potential Derby horses. In 2010, they had a likely favorite in Eskendereya, only to watch him go down with a career-ending injury less than two weeks before the race. Velazquez rode Devil May Care for Pletcher but watched Borel snatch the Derby guiding Super Saver along the rail.
The next year, he was going to ride another potential favorite in Uncle Mo. But the colt scratched the week of the race, and Velazquez hopped aboard Animal Kingdom, who beat Pletcher-trained Stay Thirsty.
"I knew how frustrating it must have been for them to win without each other," Bailey said. "Especially for Johnny watching another horse of Todd's win when he was in the same Kentucky Derby. But that's the nature of having a relationship with an outfit as successful as Pletcher's. He's going to have multiple horses, and you're going to have to choose."
Both men can rest easier knowing they won Derby No. 2 together. After more than 20 years, Velazquez and Pletcher hardly need to speak to get on the same strategic page.
"He watches the races so good that I cannot come back and lie to him," Velazquez said with a laugh. "I won't even try. When I come back and explain what happened, he gets it."
"People ask us, 'What are you guys talking about in the paddock?' And it probably has nothing to do with racing," Pletcher said. "He knows that I have confidence in him to call an audible if needed. And a lot of times you need to in racing, because when the gates open, a lot of things change … He knows I have confidence in him to do that."