Owensboro native Jeff Berry made a name for himself representing some of Major League Baseball’s biggest stars, including Buster Posey and Josh Hader. But after a high-profile exit from CAA Sports, the longtime agent has shifted his focus to another passion rooted in family tradition: horse racing. What started as a childhood love nurtured by weekends at Ellis Park has transformed into a mission to change the way people access ownership in the sport — and maybe even win the Kentucky Derby along the way.
“I grew up going to Ellis Park,” Berry said. “My dad, David Berry, who lives down here in Florida with me now, has pretty advanced Alzheimer’s, so he’s not going to be able to go to the race. He doesn’t even really know I have a Derby horse, but he’s definitely the one who first started my love of horse racing. He took me, my brother Brent, my little sister Emily, my mom Jeannie — we all would go to the track and just loved it.”
That passion took on new life when Berry joined forces with Legion Bloodstock and his Bradenton, Florida, neigbors — former MLB All-Star Jayson Werth and real estate developer Shawn Kaleta — to purchase a couple of yearlings. One of those was Flying Mohawk, a colt who recently surged into Derby contention with a second-place finish in the Grade 3 Jeff Ruby Steaks at Turfway Park.
“We went nuts. Everyone thought we won the race,” Berry said. “I’ve never seen a bigger celebration for second place.”
The race, which qualified Flying Mohawk for the Derby, marked a surreal milestone for Berry, who only recently became involved in ownership.
“I’ve only ever owned three horses in my life — and one of them ended up in the Derby,” he said.
That kind of return on investment might seem improbable, but for Berry, it’s not about the longshot — it’s about accessibility.
“We always talked about it,” he said of his childhood days with his dad and brother. “We’d say, ‘Why don’t we take some money and go claim a horse?’ But we had no idea what to do or how to get into it. That’s what we’re doing now with Jayson Werth and all of our partners with Icon Racing — we want to show people what a great sport this is, what a great family sport it is.”
Berry’s son Clark even designed the silks for Berry Family Racing, one of the ownership arms of Flying Mohawk.
“It has the B on the home plate for Berry Family Racing. As a family, we’ve been to Saratoga, Churchill Downs, Kentucky Downs. It’s been an incredible experience,” Berry said.
Though the Jeff Ruby was Flying Mohawk’s first start on a synthetic surface after exclusively racing on turf, trainer Whit Beckman saw potential.
“Whit had an idea with the way Mohawk runs, with what his skill set is, to run in the Ruby,” Berry said. “He ran great. I think he could’ve won it. I’m not sure he saw the horse on the outside that closed on him.”
Still, the result was enough to put the Derby in play. And for Berry, the decision to go was easy.
“If you earn a chance to run in the Derby — the world’s greatest race — you go,” he said. “Yes, he’s a turf horse. He’s never run on dirt. But he’s an unbelievable competitor. He doesn’t get tired. He comes off the pace. It’s like, let’s be bold.”
That same boldness led Berry to walk away from one of the most powerful positions in baseball. As co-head of CAA’s baseball division, he built a career advocating for players — sometimes to the discomfort of the league and front offices. His public fights for fair arbitration outcomes and health-first usage patterns for relievers like Hader helped define his career. But Berry said the industry’s growing devotion to “efficiency” ultimately eroded his belief in the system.
“When you see something that you believe to be wrong or unjust, and you do nothing about it, you’re really as culpable as the perpetrators,” Berry told The Athletic in 2024. “My goal as an agent was always to protect the best interests of the players, and do it in a way that I thought was honest and direct.”
After reaching a confidential separation agreement with CAA, Berry joined the San Francisco Giants front office as a special advisor to longtime client and current president of baseball operations Buster Posey. That connection created one of the more unique Derby prep experiences: the Giants opened their season in Cincinnati, and on an off day, Berry brought the entire front office — including Posey — to Turfway Park to meet Flying Mohawk.
“I’m holding Mohawk, Buster’s got a hand on him, and the rest of the Giants front office is standing there with us,” Berry said. “It’s a cool story. We watched him gallop and get a workout in. Then he shipped to Churchill.”
The scene underscored Berry’s vision for what horse racing could become — not just a pastime, but a shared experience between families, friends, and even professional sports organizations. That mission aligns with Werth’s, who launched Icon Racing to create “iconic experiences” in an “iconic sport.”
“You win with your teammates and your coaches. That’s great. But you don’t get to share that in the moment with your people,” Werth told Bloodhorse. “Horse racing gives you the opportunity to experience those moments together — with your family or friends, the people you choose to be around.”
Icon Racing is designed to bring those people in.
“I think we’ve got such a great group of people around Icon — all of our partners who’ve decided to go on this ownership journey, our trainer Whit Beckman, our ‘scouts’ at Legion Bloodstock who make recommendations on purchases, and Travis Durr down in South Carolina who coaches our youngsters we send down there to become racehorses,” he said. “It’s a complete team effort and has been a dream ride that my whole family has enjoyed.”
With Legion Bloodstock guiding the way, Icon has already made waves at major sales, including a $375,000 Nyquist filly called the “queen” of her session at Keeneland. But beyond the stats and studs, Berry said the real victory is helping others find their way in.
“This is about bringing good people into a great sport and sharing something unforgettable,” he said.
For Berry, that something now includes a shot at the Kentucky Derby.
“It still seems a little surreal,” he said. “But if you get the opportunity, you go. Why not go win the Kentucky Derby?”
