Always Dreaming schooling in the paddock at Churchill Downs

Always Dreaming schooling in the paddock at Churchill Downs

Coady Photography

Viola Brings Brooklyn to Kentucky with Always Dreaming

Childhood friends Vincent Viola and Anthony Bonomo dreaming of Derby glory together

With ceiling fans spinning high above the seats, wood floors creaking under dress shoes and high heels, and the best view of the best horses running through the upstate New York summer, the box-seat area of Saratoga Race Course is a magical place where top achievers in the sport gather to dope out the next race or socialize with one another.

The center of the social scene last August into early September was the box just past the finish line, where Vincent "Vinnie" Viola and his wife, Teresa, entertained guests and passersby non-stop. Their St. Elias Stable and Teresa Viola Racing Stable was on a red-hot streak that saw Sweet Loretta win the Schuylerville Stakes (G3) and the Spinaway Stakes (G1), Nonna Mela take the Adirondack Stakes (G2), and Ring Weekend win the Bernard Baruch Handicap (G2T).

People would try to shake hands with the couple just to have some luck rub off. Anthony Bonomo took it a step further. In that magnificent setting, he and Viola decided to join forces with their horse operations, and eight months later, Viola and Bonomo find themselves at Churchill Downs anxiously awaiting the May 6 running of the Kentucky Derby Presented by Yum! Brands (G1), where their Always Dreaming figures to be first- or second-choice in the wagering.

Viola, at 60, wears a salt-and-pepper crew cut not far removed from his days at West Point, where he ended up after a childhood lived in the Williamsburg section of Brooklyn. He grew up two blocks from Bonomo and both speak with an unmistakable New York accent—tough and funny.

"I'm a couple of years older, but we played baseball together and, you know each other from the neighborhood," Viola said on the Churchill backstretch. "When I got back into the Thoroughbreds, I called Anthony. We were doing the same thing separately, so we decided to do it together, and that's exactly what you see here."

Viola's father, a World War II veteran, took his young son to Aqueduct Racetrack in 1965 to see Kelso run there. Viola took an immediate liking to the festivities and the racetrack became a major bond between the generations.

"My father was always responsible. He was a very conservative gambler and a great handicapper," Viola said. "And he taught me risk management through gambling. He was maniacal about the movement of odds and the flow of money to different horses, and those were big lessons I learned from him."

Lessons that Viola applied after his military career, when he purchased a seat on the New York Mercantile Exchange and eventually launched a number of businesses and eventually founded Virtu Financial, which went public in 2015. Today, Viola's net worth is north of $1 billion, and he also owns the Florida Panthers of the National Hockey League. Those early days at the racetrack apparently taught him well.

As it turns out, Teresa's family also loved the races. Her grandfather was a handicapper and the horses became a bonding agent for the two families. Viola's involvement in horses deepened when he was stationed at Fort Campbell in Kentucky and went to the races at Churchill. He befriended another West Point graduate named Terry Finley, who went on to start the West Point Thoroughbreds partnership group, and who took Viola to his first Kentucky Derby in 1998.

This year, it is Always Dreaming who is taking Viola and company to the Derby. That company includes Finley, who bought a small piece of the horse after the son of Bodemeister  broke his maiden in January. He hasn't lost since, most recently romping in the Xpressbet Florida Derby (G1). Always Dreaming was a $350,000 yearling purchase out of the 2015 Keeneland September sale. He is one of 40 horses now owned together by the Viola and Bonomo families.

"We have everything from a 4-year-old to foals out of a couple of mares who we own," Viola said. "The partnership is fantastic. It's like talking to your brother. I can finish his sentences, and he can finish mine. If you can do this with friends who get along, it's fun."

Since the Florida Derby, Viola has been amped up on the upcoming classics. 

"I've been thinking about the Derby 22 hours a day," he said. "I'm confident, because I think this horse is getting ready to do something special. That's how I feel. I don't want to sound overconfident, but he's a cool horse and has a lot of class."

Always Dreaming put on a show since arriving at Churchill. He's obviously feeling well and has been throwing his body around with abandon over the racetrack.

"I'm happy the horse is demonstrating a personality," Viola said. "He really wants to run. I like that he's a little bit tough. I think he's got a little bit of that Brooklyn swagger."

Not hard to imagine where he's picked that up from.