Hip-hop just scored a massive W at the racetrack.
Listenupshance, owned by celebrity-backed Run Fast Racing, won the $400K Grade 1 Bing Crosby Stakes Saturday at Del Mar Thoroughbred Club. For Lil Wayne and Lil Yachty—the two rap titans who co-own the operation alongside Latin superstar Rauw Alejandro and thoroughbred expert Glenn Sorgenstein—this wasn’t just another day at the track. The 4-year-old gelding, ridden by Emisael Jaramillo and trained by Doug O’Neill, stayed near the front before taking the lead and holding off Maximum Bourbon by a nose. Listenupshance completed the six-furlong race in 1.09 minutes, earning the first Grade 1 victory of his career. More importantly, the win also secured him a fees-paid berth in the Breeders’ Cup Sprint at Keeneland on October 31—horse racing’s championship stage.
This is a huge moment for Run Fast Racing, the operation that’s been quietly reshaping thoroughbred ownership since early 2025. Run Fast Racing was founded by entertainment entrepreneur Adam Kluger and includes Lil Wayne, Lil Yachty, Rauw Alejandro and entrepreneur Glenn Sorgenstein. But here’s what sets this crew apart from the old-money racing establishment: the company also offers fans the opportunity to participate in the racehorse ownership experience for $100 a month. That’s not a typo. You can literally own a piece of a thoroughbred for a Benjamin a month through their mobile app.
Wayne and Yachty didn’t come into this as dilettantes. Kluger, a veteran of the music industry who formerly managed Lil Yachty, brought serious industry connections—and Lil Wayne, a lifelong sports fanatic, was simply a great fit. “Everyone involved has a passion for the sport,” Kluger says, “and believes that we can revitalize it by introducing it to a younger generation.” That mission got real when their horse Vitruvian Man competed in the 2026 Belmont Stakes on June 6, marking a genuine first: a celebrity-owned horse running in a Triple Crown race. Vitruvian Man didn’t take home the trophy that day, but the moment was seismic—hip-hop officially owned a seat in one of sports’ most exclusive rooms.
Listenupshance’s Grade 1 victory proves Run Fast Racing isn’t just a novelty play. Trained by the acclaimed Doug O’Neill, the stable has hit the ground running, finishing in the money in six of their first eleven starts. That’s a winning culture, not a celebrity vanity project. For context, MC Hammer was one of the most notable early examples of rappers in racing. His Oaktown Stable owned successful racehorses, including Lite Light, who won the 1991 Kentucky Oaks, and Dance Floor, who finished third in the 1992 Kentucky Derby. But Run Fast Racing is operating on a different scale—they’re not just buying horses; they’re rebuilding an entire industry’s relationship with hip-hop culture.
The Breeders’ Cup Sprint at Keeneland in October is one of horse racing’s blue-chip events, a $2 million purse that attracts the sport’s elite. Listenupshance’s fees-paid berth means Run Fast Racing doesn’t have to nominate—they’ve earned their seat. That’s the kind of legitimacy that turns skeptics into believers. For a sport that’s been aging out of relevance with younger audiences, having Wayne and Yachty at Keeneland in October isn’t just good optics. It’s a cultural reset.
The 16BARS take: Run Fast Racing just proved that hip-hop money, hip-hop culture, and actual competitive excellence aren’t mutually exclusive in thoroughbred racing. Listenupshance running in the Breeders’ Cup is bigger than a trophy—it’s the future of the sport showing up.
