Tom Pedulla is interviewing prominent owners, trainers and jockeys as they travel the Road to the $5 million Kentucky Derby presented by Woodford Reserve on May 3 at Churchill Downs. 

This week’s installment features Jeff Berry, a senior adviser to Buster Posey, president of the San Francisco Giants. Berry partnered with former major league All-Star Jayson Werth and noted Florida real estate developer Shawn Kaleta in owning Kentucky Derby candidate Flying Mohawk.

Although Flying Mohawk spent the early stages of his career on turf, he put himself in a strong position to make the 20-horse Derby field when he rallied to place second in the March 22 Jeff Ruby Steaks on Turfway Park’s all-weather Tapeta Footings surface. The son of Karakontie earned 50 qualifying points with that effort, leaving him 21^st on the Kentucky Derby Leaderboard since he also has $156,800 in non-restricted stakes earnings.

Berry, 55, is a former catcher who played one season in the Boston Red Sox minor league system before emerging as one of baseball’s leading agents for 26 years. The Giants hired him in December 2024. He and his wife, Sarah, have three children – Jax, 17; Clark, 14; and Whitney, 11. He contacted Werth, a long-time friend, about fulfilling his dream of owning a Thoroughbred. 

Flying Mohawk is trained by Whit Beckman and is ridden by Joe Ramos. On the advice of Legion Bloodstock, he was purchased for $72,000 at Keeneland’s September yearling sale. During a question-and-answer session conducted by America’s Best Racing, Berry reflected on his distinguished career, the thrill of having a Derby prospect so quickly as an owner, and whether Flying Mohawk can transition to dirt if, as expected, he makes the Derby field.

PEDULLA: What can you tell me about your minor league career?

BERRY: Very bad player. I played one year in the minor leagues (1994 in Class A) and then went to law school. I hit .150 and played a couple of times a month. I was not very good. I was much more successful as an agent.

PEDULLA: Did you play college ball?

BERRY: I played in college. I graduated from UNC-Charlotte.

PEDULLA: How did you get involved in racing as an owner?

BERRY: I’ve known Jayson forever. I’d heard he was doing horse racing. I’m from Owensboro, Ky., originally. I grew up going to Ellis Park. My dad would take me, my brother, my sister, my mom. We would go over to Ellis Park all the time and always loved it. I always had a great affinity for horse racing. I always had it in the back of my mind to own a horse someday. I was talking to Jayson about it and he said, ‘Let me show you how.’ And that’s how I got into it.

Flying Mohawk settling in at Churchill Downs. (Coady Media)

PEDULLA: Flying Mohawk is the second horse you owned. Don’t you know this game is supposed to be hard?

BERRY: Every game is hard. That’s the point. Every game is hard, but you don’t have the chance to win unless you lived it. If you can persevere through the valleys that come with every sport, you get an opportunity to come out the other side. It’s kind of surreal to even be in this position.

PEDULLA: What was it like to see the Jeff Ruby Steaks unfold?

BERRY: It was incredible. We came in second, but we acted like we’d won. It was a blast. We got a great ride by Joe Ramos. The guys from Legion Bloodstock picking out the horse, Whit training him, we felt good going into it.

PEDULLA: Where did that feeling come from? Flying Mohawk had not done anything special before that.

BERRY: Mohawk is an exceptional horse. He’s very competitive. He never gives up. He gives you everything he’s got. There’s not much more you can ask than that.

PEDULLA: The big question with this horse has to be whether he can handle dirt? What are your thoughts on that?

BERRY: My thoughts are that I have all the confidence in the world in Whit Beckman and what he’s doing. [The horse had] never run on synthetic, either. Mohawk works out a lot on dirt. Whit is confident. That makes me confident. We’ll be as prepared as possible. Regardless of the outcome, it’s no different than when Rocky fought Apollo Creed the first time. You’ve got to get into the ring to find out. Mohawk earned the right to be in the Derby and it’s like, ‘Let’s go for it.’

PEDULLA: Sure. Obviously, you would face long odds. Does that bother you?

BERRY: Not at all. Unless you’re in it, you don’t have a chance. We have a chance with a talented horse that competes its tail off every time. I feel great about it.

PEDULLA: Whatever the Derby brings, is the feeling with this horse that his future will be on grass?

BERRY: That would make the most sense, I guess. But the future is the next three weeks. That’s where we’re looking.

PEDULLA: Is your family enjoying the ride as well?

Jeff Berry and family (Courtesy of Jeff Berry)

BERRY: I think so. Clark designed the silks that Mohawk was running in in the Jeff Ruby. 

PEDULLA: What do they look like?

BERRY: It’s a red ‘B’ on a home plate. Really cool, right? He designed the whole thing. It was kind of cool seeing silks he designed running on national television in the Jeff Ruby.

PEDULLA: What are your impressions of Whit Beckman?

BERRY: I think he’s one of the better trainers in the game today, and I think he’s going to be one of the great ones.

PEDULLA: Are there any comparisons to be made between what it takes to be successful in baseball and horse racing?

BERRY: To me, there are parallels. Legion Bloodstock, they are our scouts. They are the guys on the front line finding our talent. Whit and his group run our player development. Travis Durr, we send all of our yearlings and 2-year-olds to him in South Carolina. He gets them ready to be racehorses. Whit takes them to the next level after that. It’s a really cool development process. To me, so much of it is about the general experience and how much fun it has been.

PEDULLA: Will Jayson’s involvement and yours encourage others from the baseball world to participate in horse racing?

BERRY: Alex Bregman is really involved in horse racing, too. He’s still an active player and doing some great things. Let’s put it this way – taking the entire Giants front office over there (to see Flying Mohawk at Turfway Park), they get to experience it. You can introduce people to the majesty of these athletes, how much fun it is, you can share it with the entire group or your family. We went up to Saratoga. I don’t think my wife has a more favorite place in the world than Saratoga. She loves it. What a beautiful place! We hope to bring a lot more people into the sport.

PEDULLA: Can Flying Mohawk handle the Derby’s mile and a quarter? 

BERRY: Mohawk, I don’t think he gets tired. He loves to run. I think the distance will be great for him. When he’s at his best, he comes from off the pace and closes at the end. We’re hoping for the same thing at the Derby.

PEDULLA: How would you rate your chances?

BERRY: Whit told me the Derby is like a street brawl. Anything can happen. Whatever the outcome, I’m proud of the whole team.