Dave Portnoy Eyes Kentucky Derby Horse Ownership: Barstool Founder’s Latest High-Stakes Play

By Jayson Panganiban April 21, 2025 12:44

Dave Portnoy, the brash Barstool Sports founder known for his high-profile bets and unfiltered takes, is flirting with horse racing’s biggest stage. In April 2025, the media mogul revealed he’d been offered a stake in a Kentucky Derby contender, sparking speculation about a potential ownership debut at Churchill Downs. While details remain scarce, the move aligns with Portnoy’s history of blending sports, gambling, and pop culture—and could reshape how younger audiences engage with thoroughbred racing.

The Offer

The proposal came via an undisclosed ownership group, offering Portnoy a minority stake in a horse eyeing the 2025 Derby trail. Though Portnoy hasn’t confirmed his decision, a TikTok clip showed him discussing the opportunity, quipping, “I’m more of a degenerate gambler than a horse guy, but how bad could it be?” The video, which amassed over 250,000 views, sent Barstool’s fanbase into a frenzy, with comments ranging from “Do it for the stoolies!” to “Name the horse ‘El Presidente’.”

This isn’t Portnoy’s first Derby dalliance. In 2024, he was offered a 10% share in a contender but passed, later joking on Pardon My Take that he “didn’t want to jinx it.” His 2019 TwinSpires appearance, where he picked Long Range Toddy to win (it finished 16th), underscores his love for the event’s spectacle—if not its profitability.

Barstool’s Derby Influence

Portnoy’s potential entry comes as Barstool deepens its Derby ties. In March 2025, the company dropped a limited-edition Kentucky Derby hat through its online store, blending Churchill Downs’ heritage with Barstool’s irreverent branding. The snapback, part of the “Run for the Roses” collection, sold out within hours, highlighting Portnoy’s ability to monetize niche sports moments.

Barstool’s gambling arm, already a DraftKings affiliate, could leverage Portnoy’s ownership for cross-promotional content. “Imagine live-streaming stable tours or letting fans bet on his horse’s workout times—that’s the Barstool playbook,” a sports marketing exec told Front Office Sports.

The Stakes

Ownership isn’t cheap. Buying into a Derby-caliber horse typically requires six-figure investments, with training and entry fees adding $50,000+ annually. But Portnoy, whose net worth exceeds $100 million, has the capital—and the platform—to offset costs through sponsorships and content.

The risk? Derby horses are longshots by nature. Just 20 horses make the gate each year, and favorites rarely win. Portnoy’s 2019 pick, Long Range Toddy, went off at 30-1 odds, while 2024’s Mystik Dan paid $39.22 to win. “You’re basically lighting money on fire unless you’re Coolmore or WinStar,” joked a veteran bloodstock agent.

Why It Matters

Portnoy’s involvement could attract younger, digitally native fans to a sport battling aging demographics. The Jockey Club reports that Derby viewership among adults 18-34 has dropped 15% since 2019, a trend Portnoy’s TikTok-friendly antics might reverse.

“Dave doesn’t just own things—he turns them into memes,” said a Barstool staffer. “If he buys in, every millennial with a DraftKings account will suddenly care about pedigrees.”

The Wildcards

Naming Rights: Barstool’s penchant for edgy humor could produce a Derby first—think Trenches Not For You or One Bite Pizza.
Celeb Synergy: Portnoy’s A-list connections (he’s partied with Gronk and Bill Burr) could lure new high-net-worth owners to the sport.
Content Gold: A Viva La Stool docuseries tracking his horse’s prep would rival Netflix’s Formula 1: Drive to Survive.

While Portnoy hasn’t committed, the offer underscores his cultural sway. Whether he becomes the next Jeff Ruby or sticks to pizza reviews, one thing’s clear: If his horse ever wins, the mint juleps will flow at the Barstool offices—and the internet will break.