Before he was a West Point grad, an Army ranger, a player on the New York Mercantile Exchange, a high-frequency trading pioneer, the owner of a hockey team in Florida, a billionaire and President Trump’s firstfailed candidate for Secretary of the Army, Vinnie Viola was just a kid from Brooklyn watching his dad study the Racing Form on the long subway ride out to Aqueduct.
Viola’s father was among the regulars who folded their newspapers and placed them in the seams of their seats to claim the seats as their own, a custom that is still part of the horseplayer’s code.
One job for the young Viola was to stand in front of the track’s tote board and watch for sudden shifts in wagering. It would help him understand numbers, and it was also “magical being next to your dad, as he was really committed to a sport he loved,” Viola said.
Once he joined the three-comma club, Viola decided he’d get back into the horse game, sans newspaper seat-saver. So he called up a buddy from the block who also learned his craft hugging the track rail and they stopped betting on the ponies and started buying them. (Full disclosure: They probably did not stop betting on them.) And because none of the 158,070 people watching Saturday’s Kentucky Derby at Churchill Downs wanted to get punched in the face—least of all the connections of the other 19 horses running, fearing an ugly scene in the winner’s circle—their horse, Always Dreaming, made their dream come true.
“Someone asked me if this is the greatest feeling I’ve ever had,” Viola said. “The answer is yes, aside from the births of my children and meeting my wife.”
Even better than when he defended her honor against that concessions worker at a horse auction. So if anyone’s feeling brave or lucky, go ahead: Try to take down Always Dreaming at the Preakness in two weeks or, failing that, at Viola’s childhood stomping grounds—Belmont Park—three weeks after that. Pro tips: Don’t wear a white shirt, and bring a dentist along to reset your teeth after Vinnie’s rearranged them all over the turf.