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BY SARAH WELK BAYNUM

For Jack Maro, a criminal defense lawyer in South Florida at the time, his first taste of a racetrack offered a rare and unique escape he fell in love with.

“Back then, my schedule was so hectic I couldn’t plan anything—no golf, no dinner reservations, nothing that required setting a time. I was juggling court dates, client meetings and constant pressure,” he said. 

But that all changed with a fortuitous favor for a friend without transportation.

“One day, a good buddy of mine, a habitual gambler, had a tip on a horse and needed a ride to Gulfstream. I gave him a lift, and it was my first real visit to the racetrack. I didn’t expect much, but something about the atmosphere just clicked. It was the only place I could drop everything in the middle of the day and disappear: no phone calls, no expectations, no one needing anything from me. I didn’t need anyone to go with me either—it was just a place to be still, alone and observe. I started going more often, getting caught up in the people watching, the horses and the pageantry of it all. There was this beautiful uncertainty to it—who will win, how will it play out? I used to laugh at the guys under the grandstand, the ones glued to the replay screens—I called them the hall monitors—like they were hoping the results would magically change.”

After some time, the racetrack wasn’t just a pause from life—it became a sanctuary.

“With my background as an English teacher before law school, I always had this sense of romanticism. The racetrack felt like a place built for dreamers and gamblers and poets, all rolled into one. Then one night at a horse sale—one of those social events where the drinks flowed freely—I wandered off and saw this horse tucked away in the corner that no one was looking at. But she had a face that stuck with me. I’ve always been a sucker for a pretty face—that’s why I married my wife, Holly: she’s smart, beautiful, the whole package. This horse had a nice eye and was dark and mysterious. I didn’t know anything about horses, but something about this horse spoke to me. Maybe it was the alcohol talking, but I raised my hand and bought her. I can’t tell you if it was logic or instinct, but I just knew. It was the horse’s eye—it saw me before I even knew I was looking. I didn’t know much about breeding back then, but I recognized the sire—probably just the Brooklyn kid in me. Her dam, Forbidden Sight, was by Bagdad, which I found intriguing. The filly I bought was named Bold Wench and she was by Bold Forbes.”

Maro’s instincts about the filly paid off—Bold Wench went on to win $450,000. After that, he was hooked and began investing in more horses.

“Once I convinced myself I could do this alone—without leaning on people who knew more than I did—I thought, ‘Alright, I’ll pair up with a trainer and this’ll go well.’ Well, it didn’t. I had moderate success, but things started shifting in South Florida,” Maro said.

Maro not only altered the strategy in managing his stable, he relocated his family and escalated his affinity for risk.

“That’s when I decided to take the next step in chasing uncertainty and move up to Ocala. Uncertainties always had a strange pull for me. Just look at my day job—I’ve been a trial criminal defense lawyer for over 50 years. There’s nothing more uncertain than a jury trial. You never know what six or twelve strangers are going to decide. The racetrack and the courtroom both live in that same world of unpredictability. That’s probably why they both hooked me.”

Over time, Maro started discovering what strategies worked—and which didn’t—in his racing business. 

“After I bought a farm up here, I loved it—the peacefulness, the rhythm of it all,” he said. “We had some success, a few stakes horses, and breeding horses that sold well. But it was never meant to be a full-time business. It was a passion project—a serious hobby. And like anything in this game, the highs were sky-high and the lows cut deep. Eventually, with all the challenges, especially finding good farm help, it became clear that big farm life was more stressful than rewarding. It was time to scale back the number of horses and breathe a little.”

Among the horses that brought him success were Proven Strategies (by Sky Mesa out of Stormbeforethecalm), who earned $378,505, and Corona Bolt (by Bolt d’Oro out of Stormbeforethecalm), who won four of six starts and earned $356,400. 

“We’ve had some luck along the way with some quality horses. We had a stakes horse we partnered on named Proven Strategies. As a two-year-old, he ran in the Breeders’ Cup Juvenile Turf in 2019 and was only beaten by about four or five lengths. We also had another special one, Corona Bolt—probably one of the fastest in the country at the time. Unfortunately, he had to undergo tieback surgery, and when they brought him back, it just didn’t hold, and they ended up retiring him,” said Maro.

Maro still fondly recalls a particularly memorable—and comical—story about a highly sensitive filly he owned.

“One of the most memorable horses we had was a tough little mare who ran at Atlantic City—nothing fancy, maybe a mid-level claimer, but all heart. Our Dominican trainer had to use an apprentice jockey one day, a kid from Venezuela, and in the paddock, he kept repeating, ‘No whip! No whip!’ The jockey nodded like he understood. The mare breaks fast, takes the lead, and is clearly going to win—she’s three lengths in front. Then, right before the wire, the kid taps her with the whip, and the filly launches him, dumps him right in the dirt. She crossed the line alone, and he nearly made it there on foot. Some horses won’t tolerate the whip, and she made it crystal clear—she was one of them!”

Despite his success, what Maro still loves most about the horse racing world is the very thing that first attracted him to it. 

“For me, the best part of the racehorse business is the pageantry—the stories and the social camaraderie. Sure, there’s a tremendous amount of heartache, but there’s also something truly sublime about the sport and business of horse racing.”

Return to the May 28 issue of Wire to Wire