Former MLBer Jayson Werth will run for the roses at Kentucky Derby 2025 with Flying Mohawk

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LOUISVILLE, Ky. — Bored and with time on his hands between games against the Louisville Bats, Jayson Werth and a few of his Syracuse SkyChiefs teammates wandered over to Churchill Downs on a random day in May, 2002.

A baseballer through and through, with genetic Major League lines tracing from his great-grandfather to his grandfather to his uncle to his stepfather, Werth knew two things about horse racing: They competed for something called the Triple Crown, and the Kentucky Derby was a big deal.

That May day, along with a trifecta, Werth hit the ninth race of the day when a horse by the name of U.S. Jets crossed first for the fifth win of what would eventually be a middling 12-win career. Werth left Churchill with $3,500 in winnings, a veritable king’s ransom for a minor leaguer.

Though he always remembered the horse’s name, he promptly forgot about the sport for the next two decades as he roared into a 15-year career in the big leagues and won the 2008 World Series with the Phillies. Twenty-three years later, Werth stands outside Barn 21, recalling that happy May day, and hoping now for an even bigger win. On Saturday, Flying Mohawk, the resident of Barn 21, will be one of 20 horses to break from the gate for the 151st running of the Kentucky Derby.

Werth is his owner.

The road from casual bettor to a man who on Wednesday afternoon was handing out MHRGA (Make Horse Racing Great Again) hats en route to a crawfish boil at his barn is indeed a pivot, but to the man steering the journey, not terribly surprising.

“Anybody who knows me wouldn’t be surprised,’’ Werth tells The Athletic by phone while tossing out hats. “My mom always says I only know how to go all in. I played baseball from the time I was five until I was 39, all day every day, and when it was over, there wasn’t much to replace it. Just this huge void.

“But this sport that I knew nothing about, it’s fascinating, it’s addicting. The people are incredible, and the animals are majestic. I love it. I love everything about it.’’

Flying Mohawk trains on the track during morning workouts at Churchill Downs (Photo: Michael Reaves/Getty Images)

Werth wasn’t sure what he was looking for when horse racing found him. Post-retirement, Werth was like a lot of athletes, searching for something but not quite sure what it was. He dabbled in organic farming, buying a 300-acre plot of land in Illinois, but he itched for something competitive.

While visiting Florida, Werth teed up for a round of golf with his friend, Rich Averill. Averill got started in horse racing the same year that Werth was cashing in on U.S. Jets, partnering on a gelding named Fun n’ Gun that year. He now has 725 starts and more than $4 million in earnings.

After their round of golf, Averill took Werth over to Tampa Downs, where some of his horses were running. As Werth watched the horses come around the final turn, he felt a very familiar surge building inside him.

“It’s like playing a big game and you’re sitting in the dugout, bases loaded, down two in the bottom of the ninth,’’ he explains. “Your teammate hits one into the gap, and you’re cheering and screaming because that’s all you can do. You’re helpless. You’re not on the field, but you’re invested in what’s happening. Those horses came around the stretch, that’s exactly how I felt.’’

Immediately hooked, he partnered with baseball agent Jeff Berry and Florida real estate developer Shawn Kaleta to form Two Eight Racing, a nod to the jersey number, 28, he wore with the Los Angeles Dodgers, Phillies and Washington Nationals. In 2023, he bought some fillies and quite literally went off to the races.

Blessed with a sweet dose of beginner’s luck, Werth made his first Derby appearance last year, as 10 percent owner of Dornoch. The horse finished 10th in that race, but went on to capture the Belmont Stakes, a moment Werth compares to his World Series victory in terms of its immediate euphoria.

That victory not only gave Werth a new jolt of competitive fire, it provided him with a dose of something he says he never felt before: nerves.

“I never experienced nerves before. Never got butterflies,’’ he says. “I’ve played with a guy who would throw up before every game, and I’d look at him like, ‘What the hell is wrong with you?’ And now here I am, fighting back puking before every race. It doesn’t make any sense to me, but I have all these crazy emotions with this sport.’’

Post Dornoch, he doubled down on both his investment in horses — he is the front and center owner for Flying Mohawk — and his commitment to the sport.

“Horse racing does a terrible job marketing itself,’’ he says, noting more than a few friends and former teammates who are skeptical about his new passion. “People think it’s scummy. The gambling, the drinking, and they hear the bad stories. They don’t see that there is more good than bad, and most of these horses are not only treated well, they’re professional athletes. Watch them and you know they want to go.’’

He has created a few converts on his own, bringing buddies to the track or to the barn to let them see for themselves the majesty of its athletes and the draw of a race day. Filled with the blush of first love for his new passion, Werth also feels compelled to spread the joy, turning himself into a self-appointed horse racing pied piper. While conducting this interview, he also yelled to passers by, “Here! Have a hat!” He loves almost everything about horse racing — “I was like the bubble boy, so I’m fairly certain I’m allergic to everything in the barn,’’ he says — and wants people to feel what he feels.

Former MLB player and co-owner of Flying Mohawk Jayson Werth poses for a photo with fans at Churchill Downs. (Photo: Michael Reaves/Getty Images)

He’s also savvy enough to understand his own personal draw. With his long hair hanging out from his fedora, he is immediately recognizable, and his MLB fame brings a different kind of attention to his horse and horse racing by extension. He knows that bringing more people with some celebrity cache will only raise the industry’s profile.

Werth did not expect Flying Mohawk to be a Derby contender, with good reason. The horse’s first five races were all on turf, and the Derby is run on dirt. But trainer Whit Beckman had a plan for the $72,000, 3-year-old. He moved Flying Mohawk to the synthetic surface at Turfway Park for the Jeff Ruby Steaks, one of the Derby prep races. When Flying Mohawk finished second there in March, he earned enough points to make it into the Derby field, setting off a celebration so boisterous that people with the actual winner, Final Gambit, wondered what Werth and his team were doing down by the winners’ circle.

Werth knows that with no real experience yet on dirt, Flying Mohawk will be a long shot (he opened with 30-1 odds), but he doesn’t care. “Owning a horse that runs in the Kentucky Derby is literally the highest level of sports,’’ he says. “It’s like getting your name called on Opening Day to run out on the field for a storied franchise like the Phillies or the Yankees or somebody like that.” He pauses for comedic effect. “Not the Mets. Never the Mets.’’

Then he’s asked to do the impossible: Where might a Derby victory line up on his personal list of accomplishments? Werth first ranks his past achievements. The World Series, he says, is number one, with the bonkers Philadelphia parade as 1A. He slides Dornoch’s win into second.

Then he ruminates for a few minutes on his own athletic foundation — the great-grandfather, John Schofield, a shortstop, whose pro career was cut short by injury; the grandfather, Dick “Ducky” Schofield, who spent 18 years in the Majors and won a World Series with the Pirates in 1960; the uncle, Dick Schofield, who spent 14 years in the bigs and also won a World Series, in 1993, with the Blue Jays; the stepfather, Dennis Werth, a former first baseman for the Yankees and the Royals; and his mom, Kim, a track star who competed in the 1976 Olympic Trials. Then he answers.

“But that’s all the foundation, what we’ve done, where we’ve been in life. This is the future,’’ he says. “To win a Kentucky Derby at this point would take over them all. This would be the highlight of my life.

“My mom raised me to be a winner, and that’s what we’re focused on. We’re not here to do anything but that. I know we’ll be a long shot. I don’t care. Once those gates open, you believe in your teammates. We’re here for a reason and we’re going for it.”

(Photo by Michael Reaves / Getty Images)

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