Keeneland's Inside the Winner's Circle: 'Dreaming' Becomes Reality

“Inside the Winner's Circle, Presented by Keeneland” is a new series showcasing graduates of the Keeneland September sale that have gone on to achieve success on racing's biggest stages.

Anthony Bonomo's voice was a bit hoarse Monday afternoon, but anyone who knows the 59-year-old is likely aware of the exact circumstances that led him to that condition. Just two days prior on a rain-soaked Saturday afternoon at Churchill Downs, Bonomo's 3-year-old colt Always Dreaming (Bodemeister)–owned in partnership with his wife Mary Ellen, longtime friends Vinnie and Teresa Viola, as well as Siena Farm and West Point Thoroughbreds–seized control on the far turn and dashed home in the slop to capture the 143rd GI Kentucky Derby by 2 3/4 lengths. Surrounded by loved ones in the winner's circle, the prominent malpractice attorney and insurer from Brooklyn celebrated with an exuberance known only by those who have been fortunate enough to take down what is arguably the most prestigious event in all of sport.

“It's the only time when grown men get to act like children and get away with it, you know?” Bonomo said Monday. “It's surreal, to be honest with you. You always think you have a good horse, but winning a race like that with 20 horses–they're all good horses, all good trainers and all good jockeys–is unreal.”

In the aftermath of the race, Bonomo was quick to deflect the credit to practically anyone associated with the horse but himself. After all, Bonomo grew up playing stickball on the streets of Brooklyn–an experience that gave him a keen sense for what it means to be part of a team, as well as some perspective when it comes to the sheer joy of winning at a competitive endeavor.

“At the end of the day, it's a team,” he asserted. “When teams win, they win together, and when teams lose, they lose together. That's the way I look at it…We've been blessed to have a great team from start to finish, from the guys picking it out to [former trainer] Dominick Schettino giving the horse his foundation to the horse's progress this year. What can you say? It's phenomenal.”

The origin of the Always Dreaming team came in the days leading up to the 2015 Keeneland September yearling sale, when Schettino–Bonomo's stable trainer at the time–agreed with the assessments of successful bloodstock agents Jimmy Crupi, Steve Young and Chris Brothers, who tabbed Hip 45 as a potential standout on the racetrack. Bonomo's son, Anthony, Jr., who spent significant time working as an assistant trainer with Schettino, concurred and sought to pursue the son of Bodemeister when he was offered on day one of Book 1 of the sale [click here for sales ring video].

Bonomo himself was no stranger to the Keeneland September marketplace. Just one year prior, Crupi snagged Greenpointcrusader (Bernardini) from the sale for $575,000 and the handsome dark bay went on to capture the 2015 GI Champagne S. at Belmont Park for Bonomo's Brooklyn Boyz Stables in partnership with his wife's MeB Racing and the Viola Family's St. Elias Stables. In 2008, one of his earliest stable stars, GI Mother Goose S. runner-up Connie and Michael (Roman Ruler), passed through the ring at the Keeneland Sales Pavilion as an $80,000 buy.

“We've always used Jimmy Crupi and Dominick Schettino, who worked very closely with my son on these,” Bonomo explained. “This horse [Always Dreaming] was on three guys' shortlists, and when that happens, you say, 'Boy, this is something we should be thinking about.' Because it's not often that everybody likes the same horse. So, [given] the fact that those people loved him…you got to go for it, and hope for the best. That's what you do. And we were lucky enough to be the successful bidder.”

Bonomo laughed and added that he was unaware that his son had ponied up $350,000–an over-bid from his stated $250,000 limit–because he was in a business meeting at the time when Always Dreaming entered the ring.

“My son over-bids; how do we wind up with him and get to where we are?” Bonomo said, clearly still considering the enormity of the moment. “It takes a team, and the team changes along the way, but no one should be lost. I didn't do anything–I wrote a check. How easy is that?”

While Always Dreaming was transferred to the care of leading trainer Todd Pletcher after finishing third and second in two starts as a juvenile in the summer of 2016, Bonomo praised his long-time friend Schettino for the role he played in the colt's development. Bonomo classified Schettino as an “underrated” trainer and explained that the shift to the Pletcher barn was purely a business decision and a byproduct of his merger with the stables of Vinnie and Teresa Viola, who use Pletcher as their primary conditioner.

Given time to mature through the autumn, Always Dreaming returned to the races with a dominant maiden victory at Tampa Bay Downs Jan. 25 and added an easy wire-to-wire score in a Gulfstream Park optional claimer Mar. 4. The dark bay landed Bonomo and friends back in the Grade I winner's circle with a decisive tally in the Apr. 1 GI Florida Derby–a triumph that was, in retrospect, a mere precursor to the fanfare that would follow his success beneath the Twin Spires five weeks later.

“The win is great, but when you're around your family and friends and loved ones, and something like this happens, it's impossible to describe,” Bonomo said of the race's aftermath. “It's such a hard business that any win is unbelievable.”

After building his stable from the bottom up, Bonomo maintains a level-headed outlook as Always Dreaming sets his sights on the “Middle Jewel” of the Triple Crown, the May 20 GI Preakness S.

“He came out of the race very well, he looked great and he had a nice clean trip–he didn't get bumped around, like some of the other horses,” the owner noted. “He looked lively the next morning, he was looking for his peppermints. And he got a few, believe me…He's always trained well, he looks good, and hopefully the next two weeks will be good to him and he can get into that race and run to his ability. All you can ask is that if a horse performs to 100% of his ability, hopefully that's good enough. There are no givens in this business.”

But nevertheless, it's only natural to wonder if a kid from Brooklyn may have hit the jackpot with a 3-year-old colt realizing his considerable talent at the perfect time.

“What's wrong with dreaming?” Bonomo quipped. “Maybe we'll have to name our next horse Keep Dreaming.”