Skip to main content
Original Issue


Owned by good friends and trained and ridden by one of racing's top combos,ALWAYS DREAMINGproved more than a match for the field and the slop at the Kentucky Derby

THERE IS a frozen moment, right before the start of the Kentucky Derby. It is a moment of infinite possibility, in which every horse runs with wings, every bet is cashed, and the racetrack is once again a cathedral of sport. Last Saturday it looked like this: 20 horses rocking in the starting gate, a hulking piece of green iron, well past the top of the home stretch, almost to the brick wall that separates Churchill Downs from the street beyond. Late afternoon sunshine slanted across a racetrack slick from three days of rain, like a sheet of brown ice. It sounded like this: a buzz, a gasp and then a roar from the throats of nearly 160,000 fans who had waited a year to witness this again. And it felt like this: a question, about to be answered at last.

The winter and early spring had been mostly empty. Promising young horses had run fast, and then slowly. They had been healthy, and then injured. They had won, and then they had lost. There was no front-runner in the class. Mastery, trainer Bob Baffert's colt, might have been the favorite, but he was injured in March, a symbolic blow. On the day before the Derby, Baffert's horse Abel Tasman won the Kentucky Oaks, a race for 3-year-old fillies that is famous inside racing but largely unknown outside it. Afterward Baffert promised that clarity would come in the Run for the Roses. "There hasn't been a horse that separated himself from the pack," said the white-haired man who has the most familiar face in racing. "The Kentucky Derby will do that."

Yes, the Kentucky Derby did that. It was a bay colt named Always Dreaming—such a racing name, emblematic of the blind faith that comes with every yearling purchase and every $2 wager—who circled the Downs oval and flashed beneath the iconic twin spires, nearly clean despite the mud beneath his hooves, winner of the 143rd running by 2¾ lengths over long shot Lookin At Lee. The victory was the second in the Derby for trainer Todd Pletcher and also the second for jockey John Velazquez, but the first together for two men who are as close in their profession as Belichick and Brady are in theirs, winners of hundreds of races together, worth tens of millions of dollars.

It was a victory measured by the bonds of family and friendship. Not only are Pletcher and Velazquez among the closest of trainer-jockey combinations in the sport, but Always Dreaming's principal owners, Vinnie Viola and Anthony Bonomo, are also close friends dating back more than five decades to their Williamsburg neighborhood in Brooklyn, where they met on a baseball diamond before either was 10. Viola's father, a truck driver, introduced him to racing, and he and Bonomo would sneak under the fence at Aqueduct and bet a buck or two against each other on the races. On April 30, Velazquez won a race at Belmont Park on a Viola-Bonomo horse named Army Mule. (Viola is a West Point graduate who made millions on Wall Street. In December he was asked by President Trump to be Secretary of the Army, but he declined because of the complexity of his business holdings; he is also owner of the NHL's Florida Panthers.) After the race Viola and Bonomo took Velazquez to their favorite restaurant, Bamonte's in Williamsburg, and there they presented him with a Catholic scapular necklace, which was then blessed by their friend Monsignor Jamie Gigantiello, who is known for the reality series Breaking Bread.

"I told the monsignor we needed some divine intervention," said Bonomo. Velazquez wore the scapular in the Derby. "I said to my wife, 'Johnny rode that race with my dad and Anthony's dad on his shoulders,'" said Viola.

Bonomo, 59, had bought Always Dreaming for $350,000 at the Keeneland yearling sales in September 2015. Sort of. In truth, Bonomo's son, also named Anthony, did the bidding. "My father told me, 'Stay within the budget,'" Anthony said after Saturday's victory ceremony. "The budget was $200,000. I called my father and said, 'I went a little over.'"

Always Dreaming ran twice last summer for trainer Dominick Schettino, finishing third at Belmont and then second in a maiden race in August at Saratoga. At the time Bonomo, who made his fortune running a medical-malpractice insurance company, was the sole owner of the horse, but he had endured some recent difficulties. Most notably, in 2015, he took a leave of absence as chairman of the New York Racing Association over allegations he provided a no-show job to the son of a state politician who was later convicted on corruption charges, partly on the strength of Bonomo's testimony. Additionally, Bonomo was in the process of reducing the size of his stable, which had grown to as many as 50 horses but is now closer to 20. "It was getting uncontrollable," Bonomo said on Monday. "The deal with Vinnie [on Always Dreaming] helped me with that, but it wasn't the reason. We wanted to do something together."

They transferred training responsibilities to Pletcher, who decided that Always Dreaming needed a rest. The colt was shipped to Florida but didn't resume workouts until December. Always Dreaming won his first race back, at Tampa Bay Downs in January, and an allowance race at Gulfstream Park in March. But then Pletcher chose to skip the Fountain of Youth Stakes and go all-in on the Florida Derby, where Always Dreaming would need a strong performance to earn enough points just to get into the Derby. It was a bold play, and Always Dreaming won the mile-and-an-eighth race by five lengths in an impressive 1:47.47 seconds.

ALWAYS DREAMING arrived in Louisville almost two weeks before the Derby and immediately became rambunctious in his morning gallops. Ten days before the race, Pletcher sat in his Churchill Downs office and said, "He's trying to run the Kentucky Derby at 5:45 on Wednesday morning." Pletcher is the General Motors of modern trainers, a practical, taciturn man for whom the addition of a modest salt-and-pepper goatee is considered a radical play. He worked the problem, training Always Dreaming in draw reins, which allow the rider to better control an aggressive horse. "I was nervous watching him gallop because for whatever reason, he was ready to run upon arrival," said Pletcher.

It had been a wildly inconsistent prep season for 3-year-olds. Classic Empire, the 2-year-old champion, had been injured in a February race and refused to train several times until winning the Arkansas Derby at the 11th hour. Irish War Cry had dominated the Holy Bull in February, but ran a dull seventh on the same track a month later before winning the Wood Memorial in April. McCraken won the Tampa Bay Derby in February, but then struggled for two months with an ankle injury and his own training reticence before grinding out a third-place finish in the Blue Grass Stakes. Then there was Mastery, the brilliant winner of the San Felipe Stakes at Santa Anita in March, who abandoned the Derby trail after breaking an ankle.

Then came a bleak Derby weekend. Rain arrived on Thursday and did not fully stop until early afternoon on Saturday. The sloppy track began to dry, but another downpour three hours before post time guaranteed a messy racing surface. That was ideal for Always Dreaming, who wanted to go to the front. Both Friday and Saturday, horses that gained the lead were often able to stay there in the slop, which can be less tiring than a thick, drying track. "The last rainstorm helped us," Pletcher said on Sunday. "Kept it sloppy."

Always Dreaming drew the number 5 post and was sent off as the 9--2 favorite. Early on, Velazquez settled into second, behind State of Honor, who went off at 54--1. The early fractions were solid, 22.70 seconds for the first quarter-mile and 46.53 for the half, but the pace slowed gradually.

Into the second turn, State of Honor gave way, but Irish War Cry loomed on the outside. "It's on!" shouted Viola from his finish-line suite. It was not on for long. Turning for home, Velazquez finally allowed Always Dreaming some rein and the colt popped into open space. Irish War Cry faded. "After that," said Velazquez, "it was pretty easy." The finishing time was a mediocre 2:03.59 for the 1¼ miles; each of his five quarter miles was slower than the previous one.

BEHIND THE winner in fourth place was Classic Empire, who never had a chance. Breaking from the number 14 post, he was part of a violent, chain-reaction collision out of gate that started when Irish War Cry, in number 17, ducked—or was guided—hard to the inside, smashing into McCraken, who then banged against Classic Empire. "[Jockey] Julien Leparoux told me he almost came off the horse," Mark Casse, Classic Empire's dejected trainer, said outside his barn early on Sunday. Classic Empire's right eye was swollen shut from the collision, yet he had fought to a fourth-place finish. Casse would like another shot at Always Dreaming. "If the eye is good," he said, "I think he would do very well in the Preakness." (Watching the Derby from his home in California, Baffert said, "Best horse won. Classic Empire is the only horse that can turn the tables on him. Brutal start ...")

Always Dreaming will be there, waiting at Baltimore's crumbling Pimlico Race Course for the second leg of racing's Triple Crown. Since American Pharoah ended the 37-year Triple Crown drought in 2015, the heavy weight of desperation has mercifully been shed, but it remains among the rarest achievements in sports. It shows its face seconds after the Derby winner flashes beneath the wire.

Yet racing, burned so often, knows better than to anoint early, and best of all to simply embrace a moment. A young horse ran fast in sunshine and slop, and a sport exhaled. This is enough for now.

Ten days before the race, Pletcher sat in his Churchill Downs office and said, "He's trying to RUN THE KENTUCKY DERBY at 5:45 on Wednesday morning."