Although the family doesn’t often have the opportunity to take traditional family vacations, they work around the racing circuit to spend time together as much as possible. They all assembled last summer in Saratoga Springs, N.Y., during Saratoga Race Course’s boutique meet. Bailey spent the summer working in the New York Racing Association’s press office at Saratoga. No doubt Jacob, who was the memorable 10-year-old shown in Hennegan’s documentary unrolling stacks of cash he’d won on the ponies, was busy handicapping the races and picking winners.
Back in 2006, when Hennegan and Romans originally hooked up, the director and his brother were looking for trainers to star in The First Saturday in May. The film followed six trainers and their horses along the path to the Kentucky Derby. It was a combination of Romans’ sense of humor and overall personality that persuaded Hennegan to showcase him as a representative of the game.
“The more I learned about him — in being a lifelong horseman, working for his dad, and spending the summers in an office in Ellis Park with no air-conditioning when he was a teenager,” says Hennegan, “I was just like, win, lose, or draw, whatever happens to his horses, this is just the guy that we feel the rest of the world would like and find interesting.”
Derby Day starts early for Romans, and if he’s lucky enough to have a starter in this year’s race, it will again. His routine — he’s had three starters in the Derby since 2006 — doesn’t change. He arrives at the racetrack in the morning to tend to his horses, making sure all are healthy and ready for the day’s races. (There are, after all, 12 other races on the Derby Day race card.) When he returns home a few hours later, he puts on his suit and gathers the 30 or so family members and close friends who have assembled at his house to attend the Derby. He distributes tickets and assigns transportation before the group heads off to the racetrack.
But not even his fancy duds can pull Romans out of his typical role of regular guy. “I don’t know how Todd Pletcher and Wayne Lukas do it,” Romans said last year after the Preakness. “They look so pristine all the time. I walk to my car and I’m sweating and wrinkled. (My friend) told me I was the best he’d ever seen at making an expensive suit look cheap.”
Most of his guests watch the races from the clubhouse, but Romans splits his time between the clubhouse and his backside barn, where he caters in barbecue for the workers. As race time approaches, he and a small group of the original 30 — his brothers, Fox and the kids, the horse owners, and one or two other close friends — make their way to the backside to escort their Derby contender to the paddock. The half-mile walk from the backside barn to the racetrack is lined with Derby fans cheering on the horses and their connections.
“The walkover is probably the coolest thing about the Derby that not many people even know about,” Romans says. “It’s like the tension starts to build, and you can tell everybody’s excited with each horse.”
From there, fate and fitness take over. Win or lose, after Derby 138, Romans will have his after-party. And his after-party tradition. Typically on the Sunday after Derby, the Romans family and whoever has remained at their house will make a quick trip to the track, followed by breakfast and maybe a round of golf.
“We drive around through the infield just to see how messy it is and watch them clean it up, which is always kind of fun,” Romans says. “You see some interesting things every year.”
But things could change if the trainer Louisville calls its own finds his own way to the winner’s circle on this first Saturday in May.
“I would say if we won the Derby, it might get a little out of hand,” Romans says. “Every year you’ll read the article that so-and-so won the Kentucky Derby and he was right back at the barn at 4:30 the next morning. That ain’t going to be me. I’ll show up in a day or two.”