At Kentucky Derby, Always Dreaming Produces a Winner’s Circle Reunion Party

Each had won a Kentucky Derby, too.

Pletcher trained Super Saver, who ran away with the 2010 race on a sloppy track that looked a lot like the one here Saturday. But another rider, Calvin Borel, was on board. The next year, Velazquez visited the winner’s circle with Animal Kingdom, but he was riding for another trainer, Graham Motion.

After all they had done together, it felt as if they were cheating on their wives.

No more. They were reunited by the headstrong colt Always Dreaming, who skimmed over the soupy stretch of Churchill Downs on Saturday to win the 143rd Kentucky Derby.

It would be nice to be able to describe a dramatic race. But Velazquez and Always Dreaming fired out of the gate and sailed along the sodden track as if riding the tide. Once they shook loose Battle of Midway at the mile mark, everyone else was running for second place.

“He was ready to run,” Velazquez offered, echoing the understated manner of Pletcher, his longtime friend.

Here is the data: Always Dreaming landed his owners a $1,635,800 first-place paycheck. He completed the mile and a quarter in 2 minutes 3.59 seconds and returned $11.40 on a $2 bet to win. Lookin at Lee finished second, two and three-quarters lengths back, and Battle of Midway hung on for third.

It was a victory in the sport’s headline race, won by a trainer and a jockey united by New York and a colt owned by New Yorkers who know their way around a headline. Always Dreaming is owned by Anthony Bonomo, a New York lawyer, and Vincent Viola — a billionaire Wall Street trader who was President Trump’s nominee to be the secretary of the Army until he withdrew his name in February, citing his business ties.

Viola is also the owner of the N.H.L.’s Florida Panthers, and perhaps appropriately, the Stanley Cup paid a visit to Always Dreaming at Barn 40 on Saturday morning.


Always Dreaming, right, with Velazquez aboard, leading the field on Saturday.

Jamie Rhodes/USA Today Sports, via Reuters

“There’s no feeling like this,” said Viola, whose love of racing was stoked by a trip to Aqueduct in 1965. “From that moment, I’ve been passionately attached to this sport,” he said.

Always Dreaming arrived in Louisville as a likely favorite after a big victory in the Florida Derby and timed workouts that harked back to the most recent big horses, American Pharoah and California Chrome.

Then the wheels came off.

In the days leading up to the Derby, the colt showed up each morning as if he were being led to a rodeo chute. He bucked, balked, bolted and basically acted like an adolescent being hauled to summer school.

It forced Pletcher to be part horse mechanic, part horse whisperer. He changed the colt’s workout equipment, employing more constrictive reins. He put a different exercise rider on his back.


Vincent Viola, an owner of Always Dreaming and President Trump’s first pick for Army secretary, holding the trophy.

Jamie Rhodes/USA Today Sports, via Reuters

“There were a few anxious moments earlier in the week,” Pletcher conceded. “For whatever reason, he was ready to run upon arrival.”

The morning drama fed into a bigger narrative. As successful as Pletcher had been, he had developed a reputation as a top horseman with top horses who had trouble wining the biggest race.

Pletcher was 1 for 45 in the Derby when the gates popped open, a number that even he found troubling. He annually has 100 or more horses in training and operates his stable like a megacorporation, running horses daily on tracks all over the country.

“To me, it felt like I really needed that second one,” Pletcher said. “The first one was extra special. I have a tremendous respect for the race, tremendous respect for how difficult it is to win.”


Velazquez after the race on Saturday; he also won the 2011 Derby with Animal Kingdom.

Mark Zerof/USA Today Sports, via Reuters

But as a difficult week progressed, the normally taciturn Pletcher displayed some humor that showed that he believed in his colt. He arrived sporting a goatee as steel gray as his close-cropped hair. When asked why, he told a story about being stared at by a woman at the airport.

“I know you,” he recalled her telling him. “You are D. Wayne Baffert.”

His first job was as an assistant to D. Wayne Lukas, one of the greatest trainers in the sport; Bob Baffert, along with his white hair, won the Triple Crown with American Pharoah in 2015.

“I knew I had to change my look,” Pletcher said.

And his luck.

So in the paddock on Saturday, he gave Velazquez a leg up on Always Dreaming, assisting his old friend just as he had 20-some years ago on an inexpensive claiming horse.

As he had back then, he told Velazquez that he would meet him in the winner’s circle.

“We needed one together,” Pletcher said.

They are no longer as young as they once were. But that made Saturday better.

“I really think being behind me for 24 years together,” Velazquez said, “that’s a long time for him to still trust in me and give me the opportunity — it’s not very often it happens in this business.”

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