Sports

Lil Wayne and Lil Yachty Win Big as Their Racehorse Nabs $400,000 Derby Prize

Listenupshance, a horse that Weezy and Boat co-own through Run Fast Racing, held on by a nose to claim the Bing Crosby Stakes and a spot in the Breeders' Cup.

(L-R) Lil Wayne and Lil Yachty.
Miikka Skaffari/WireImage | Craig Melvin/WWE via Getty Images

Key Takeaways

  • Lil Wayne and Lil Yachty's co-owned horse Listenupshance won the Grade 1 Bing Crosby Stakes at Del Mar, earning over $400,000 and a fees-paid spot in the 2026 Breeders’ Cup.
  • The four-year-old gelding, trained by Doug O’Neill and ridden by Emisael Jaramillo, went off at 5-1 and held off Maximum Bourbon by a nose for Jaramillo’s first U.S. Grade 1 win.
  • Originally bought for $10,000 and intended to be dropped in class and sold, Listenupshance instead became a surprise star for Adam Kluger’s Run Fast Racing, boosting his record to 4-3-3 with $438,570 in earnings.

Lil Wayne and Lil Yachty have a lot to smile about, after a racehorse they co-own just earned them a pretty big bag.

Listenupshance, a four-year-old gelding the rappers share ownership of through Run Fast Racing, captured the Grade 1 Bing Crosby Stakes at Del Mar on Wednesday (July 29), delivering more than $400,000 in prize money and a fees-paid berth in the 2026 Breeders' Cup World Championships at Keeneland in October.

Run Fast Racing, the stable founded by music industry veteran Adam Kluger, counts Weezy, Boat, and Rauw Alejandro among its partners.

Listenupshance went off at 5-1 on race day after opening at 12-1, trained by Doug O'Neill and ridden by jockey Emisael Jaramillo. It was the first Grade 1 victory in the United States for Jaramillo, a 13-time leading rider in Venezuela who relocated to Southern California earlier this year.

Wayne and Yachty's horse edged Maximum Bourbon by a short nose, with Moonlight finishing third. The heavily favored Cornucopian, trained by Hall of Famer Bob Baffert, was pulled up around the far turn and vanned off

Jaramillo described his ride as a game of patience. "My plan was to break in front, but that didn't happen. I got away just a little bad. So I followed the eight horse and waited for my chance. He made the lead for me at the half, then we went on from there. He just had enough at the finish," he said (via Del Mar Thoroughbred Club).

The victory makes for one of the more unlikely origin stories in recent racing memory. Listenupshance was purchased at the Fasig-Tipton Fall Yearling sale for $10,000, and Run Fast Racing originally acquired the horse with the plan to drop him in class, let him lose, and sell. The only reason that plan fell apart: the target race overfilled.

"We're not even supposed to have this horse," Kluger said, per LA Mag. "He was bought to drop and lose. If that race had not overfilled, we would not own this horse. The narrative is so wild."

The win is Listenupshance's first Grade 1 title and pushes his career record to 4-3-3 across 13 starts, with total earnings now at $438,570.

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