05/03/2017 2:00PM

Viola's financial and racing acumen pay off with Always Dreaming

Barbara D. Livingston
Childhood friends Vinnie Viola (second from left) and Anthony Bonomo (left) are among the owners of Kentucky Derby contender Always Dreaming. They pose with Terry Finley of West Point Thoroughbreds (second from right) and Anthony Manganaro of Siena Farm (right) at Churchill Downs.

LOUISVILLE, Ky. – Some of Vinnie Viola’s earliest memories as a child are of going to Aqueduct and Belmont Park with his father, who would put his son right in front of the tote board with specific instructions to watch the fluctuation of odds.

“My father handicapped and bet every day,” Viola said. “He would tell me to try to memorize every change in the last two minutes before post time of every horse. I think it greatly helped me when I got to Wall Street. It made it a lot slower for me as I got comfortable with the movement of numbers to risk.”

A financial success on Wall Street, Viola has built a powerful racing stable over the last few years, coupling family and friendships along with smart advisers to buy horses who can compete at the highest level. On Saturday, Viola, his wife, Teresa, and myriad friends will seek the ultimate racing prize when they run Always Dreaming in the 143rd Kentucky Derby at Churchill Downs.

Always Dreaming, the Florida Derby winner and unbeaten in three starts this year, drew post 5 and was installed as the 5-1 co-second choice in the 20-horse field by Churchill linemaker Mike Battaglia. He is trained by Todd Pletcher.

Viola, 61, has been involved in horse ownership over two periods. He first owned horses in the late 1990s, claiming horses and buying horses of racing age at auctions. Viola was required to divest his racing interests when he was part of a group that purchased the New Jersey Nets of the NBA in 2004. Viola and his partners sold the Nets in 2010, and two years later, Viola reentered the racing game. Though he now owns the NHL’s Florida Panthers, that league did not require him to cut ties with horse racing.

:: ROAD TO THE KENTUCKY DERBY: Prep races, point standings, replays, and analysis

Viola said he contacted three people when he decided to get back into ownership – childhood friend and horse owner Anthony Bonomo, Terry Finley of West Point Thoroughbreds, and Mike Repole, another successful businessman and horse owner.

At first, Viola was involved in partnerships with West Point Thoroughbreds. Viola and Finley were acquainted from their ties to the U.S. Army. Viola graduated from West Point in 1977 and served in the 101st Airborne Division. His ties to the military are still strong, and after the terrorist attacks of 2001, he formed the Combating Terrorism Center at West Point.

Viola and Bonomo were longtime friends, having grown up together in the Williamsburg section of Brooklyn. Though two years apart in age, they played sports with and against each other.

The Violas and Anthony Bonomo and his wife, Mary Ellen, also partnered on some horses, most notably Greenpointcrusader, the winner of the Grade 1 Champagne in 2015. The Violas won that year’s Breeders’ Cup Dirt Mile with Liam’s Map, whom they owned in partnership with West Point.

Last fall, the Violas and Bonomos merged their operations when Anthony Bonomo’s stable dwindled due to financial difficulties. Always Dreaming was originally the property of the Bonomos and then-trainer Dominic Schettino, for whom the horse made his first two starts.

“It’s very easy between the two of us,” Viola said. “I think it’s because there’s a very strong feeling that’s central to who we both are about humility and feeling very humbled about just being here. Going to the track with our dads and our uncles, we were the kids who collected tickets to see if anybody threw away a winner. That’s the starting point for this journey.”

Bonomo said his own Thoroughbred business had become unwieldy, and he needed to make a change. Teaming with Viola enabled him to own smaller pieces of more horses.

“It was very time consuming,” Bonomo said. “Vinnie and I have been friends for such a long time, to do something together was great. It made logical sense to do it this way.”

In addition to racing, Viola and Bonomo will sell horses at auction. Their Orb colt was the $1.25 million sales-topper at the Ocala Breeders’ Sales Co.’s March sale.

Viola made news when he was nominated by President Donald Trump to be secretary of the Army. Viola said he had to turn down the nomination because of potential business conflicts. Among other businesses, Viola is the founder and president of Virtu Financial, one of the largest high-frequency trading and market-making firms in the world.

“It was impossible for me to meet the business-conflict ethic standards and not disrupt several of the companies I started and owned,” Viola said. “I was very humbled and honored and heartbroken I can’t do it, but I’m comfortable with my decision.”

Viola was also comfortable with his decision not to run Battalion Runner in the Kentucky Derby. Though he had enough points to get into the race, Battalion Runner did not train up to Pletcher’s expectations. Viola owns Battalion Runner by himself and said that had he run him, he most likely would have brought Bonomo in as a partner.

“If he was doing super-fantastic, I probably would have sat down with Anthony and worked something out,” Viola said. “We still may do something with Battalion Runner.”

For now, the focus is on Always Dreaming. Though the horse has trained aggressively, to the point where Pletcher has had to change equipment and exercise riders this week, Viola is confident that Always Dreaming will run well in the Derby.

“I expect a very special race from this horse,” Viola said. “I would be surprised if he didn’t do something special on Saturday.”