Whether in baseball or horse racing, Jayson Werth isn’t afraid to take a big swing.

It’s something he has continued to do since retiring from Major League Baseball seven years ago. These days the former All-Star outfielder is either spending his time preparing to launch his upcoming cannabis project, Wyvern Botanicals, or recruiting prospective investors for his new horse syndicate, Icon Racing.

“As far as life goes right now, it’s just weed and horses,” Werth said in a video interview.

The latter is his highest priority, though, as he finds himself with a horse in the Kentucky Derby for the second year in a row. He’s the co-owner of Flying Mohawk. The 3-year-old dark bay colt, sired by former Japanese-bred standout Karakontie, has recently emerged as an intriguing prospect that could surprise the field at Churchill Downs on Saturday. It’s a different circumstance from last year, when Werth owned a 10% stake in Dornoch, a now-retired colt who entered with far higher expectations as the direct brother of 2023 Derby champion Mage.

Dornoch finished 10th in the Derby last year but followed up by winning the Belmont Stakes a month later—Werth’s biggest sports-related achievement since helping the Philadelphia Phillies win the World Series in 2008. A year later, the 45-year-old returns to the Run for the Roses looking for his second win in a Triple Crown race, strapped with more ownership experience as a growing player in the horse racing community.

“I know what I’m getting myself into this time,” Werth said. “Dornoch, I love that dude … He laid the blueprint down, and now we know what we’re doing. We know a lot more about the sport. It’s pretty cool to get another chance at a once-in-a-lifetime opportunity.”

Flying Mohawk, looking to find some luck on dirt at the No. 11 post position, enters the 151st annual race on Saturday after a runner-up finish behind Derby contestant Final Gambit on a synthetic track in the Jeff Ruby Steaks at Turfway Park last month.

Alongside former CAA baseball agent Jeff Berry and real estate developer Shawn Kaleta, Werth owns 50% of Flying Mohawk through his personal stable Two Eight Racing (referencing his former baseball number). While he still has ownership in horses from his personal stash, he’s been more focused on his wider ambitions to build one of the most successful syndicates in the sport. But he understands that he cannot do that alone.

That’s why he started Icon Racing, a syndicate with a range of partners raising capital that will be used to invest in yearlings with Triple Crown potential. It’s a traditional partnership with a new-age twist, as it also has a digital media component and plans to host tentpole events for partners. Werth says the criteria to become a stakeholder isn’t too strict. “Just don’t be a douchebag,” he said. “And make sure you’re here to have fun.”

A Washington Nationals Ring of Honor member, who had a 15-year MLB career, Werth says he relates thoroughbred ownership to buying a lottery ticket, season tickets for your favorite sports team and a boys trip to Las Vegas all rolled up into one experience. Werth has found success as a relative newcomer but says it’s unsustainable to be in Triple Crown races regularly without improving his odds with more partners, capital and expertise.

“If you want to run at the top of the sport, you need to have numbers and deep pockets,” he said. “That’s what this sport needs is more people owning horses and not just betting on the horses. It’s like owning your own sports franchise with a connection to the horse that can’t be explained.”

Werth, who is featured in Netflix’s new series Race for the Crown, is the latest standout sports figure to get involved in horse racing. Former New York Yankees manager Joe Torre, St. John’s head coach Rick Pitino, former San Antonio Spurs guard Tony Parker and Denver Nuggets superstar Nikola Jokić, for example, have all owned competitive horses. Werth’s Icon Racing, which has raised more than $3 million and currently has nine horses, also aims to help other former pro baseball players and athletes to get involved while addressing the barrier of entry into the perceived elitist sport.

“When you get away from competing, you forget what it’s like on gameday—walking out of the tunnel or coming out onto the field,” he added. “It’s a great outlet for anybody who has played sports at any level and it [makes you] appreciate the gameday rush of horse racing.”

Werth, Kaleta and Berry, the last of whom is now a special advisor with the San Francisco Giants, are ready for the gameday rush with $3 million on the line for Saturday’s first-place winner. The Flying Mohawk ownership group, which has strong baseball ties, sees parallels to the nation’s oldest pastime.

“Success rates are similar, and you take big swings,” Werth said. “You can get hot or go into slumps. It’s all part of the reason why I love it so much.”