Viola Dreams of Derby Double with Vino Rosso

With 20 horses set for the May 5 Kentucky Derby Presented by Woodford Reserve (G1), many with multiple owners, it seems there are about 100 people walking around the Churchill Downs backstretch campaigning a candidate in the Run for the Roses. Only a couple, however, can say they are going for two Derby wins in a row.

In that exclusive group are Terry Finley and Vincent Viola, friends from their days at the U.S. Military Academy in West Point, N.Y. While Viola and his wife, Teresa, were the principal owners (along with Anthony Bonomo, a childhood friend of Viola's) of 2017 Derby winner Always Dreaming, Finley's West Point Thoroughbreds bought into the colt last spring.

This year, the Violas are back as co-owners (with Repole Stable) of Wood Memorial Stakes presented by NYRA Bets (G2) winner Vino Rosso, while Finley's partnership group recently purchased an interest in Stonestreet Lexington Stakes winner (G3) winner My Boy Jack.

The experience a year ago shows in Viola's relaxed countenance around the backstretch. The financial guru, dressed casually and having lost considerable weight since Always Dreaming's special day in the sun, is unfazed by any potential pressures this time around.

"Last year was an enormously intense experience, one that certainly lent itself to anxiousness," said the personable Brooklyn native. "This year, I know what to expect and I'm enjoying it so, so, so much. It's different, having the blessing of having won it.

"As an owner, you put pressure on yourself because you buy these horses, and it's like adopting them into your extended family. For me, the pressure is in hoping the horse does well for his own sake. You want them to perform up to their potential. If a horse doesn't do well, I always question whether I'm doing the right thing by racing it. I really do find myself putting the horses first."

Viola went to Aqueduct Racetrack with his father in the mid-1960s to see Kelso run, and he spent many Saturdays with his father there or at Belmont Park until he left for West Point. He then became a trader in the New York Mercantile Exchange and launched several companies before founding Virtu Financial in 2008. Viola also owns the Florida Panthers of the NHL and spends a lot of time in the Sunshine State.

Viola met Repole about 20 years ago when he was putting together a group in an attempt to buy the NBA's New Jersey Nets. The two found they had a lot of common interests, including horses, and when Viola decided to get back into Thoroughbreds (he had owned a couple of horses with his father in the 1990s), he called Finley, Bonomo, and Repole for advice. Bonomo and Repole both touted J.J. Crupi as someone he should enlist to pick out horses.

For the past two or three years, Viola and Repole have bought a handful of colts together. Crupi bought Vino Rosso (Italian for "red wine"), a colt by Curlin  out of the Street Cry mare Mythical Bride, from breeder John Gunther's Glennwood Farm consignment for $410,000 at the 2016 Keeneland September yearling sale.

"Mike and I have loved this horse from the moment he hit Jimmy Crupi's farm," Viola noted. "He is the coolest horse you've ever been around in your life. His first few races he was so calm and cool, you almost had to shake him to get him to realize how great he was. He's a prodigy. But since the Wood Memorial, he's shown us focus, seriousness, and confidence every time he steps on the track. We're over the moon with his last breeze (April 27)."

Viola still owns horses with Bonomo as well. They grew up two blocks from each other in the Williamsburg section of Brooklyn and used to sneak into the racetrack with a couple of bucks between them and persuade someone to make a bet for them. Now 62, Viola will have no such adventures entering Churchill Downs May 5.

"On one hand, it seems like just a moment ago when I was jumping up and down when Always Dreaming crossed the finish line," he said. "On the other hand, it's been an interesting and long year. Talk about guilt, right? Part of me says I have an embarrassment of riches to have another horse with this opportunity. It's unbelievable."