Adam Kluger, the man who runs Run Fast Racing, wanted to give Lil Yachty the thrill of watching a horse the rap star was invested in win a race at a place such as Del Mar during the summer of 2025. Easy as pie, right? All Kluger had to do was buy a horse for $30,000, drop him into a $10,000 claimer, and smile for the camera, even though losing him would be a sure thing.

Only problem was, the race overfilled and the horse in question — let's call him Listenupshance — ended up running in an $80,000 optional claimer at a five furlongs on the Del Mar grass instead, shunned at odds of 17-1.

Click to subscribe!

Then he wins, and the script is flipped on its head.

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

So was the scene unfolding behind Kluger as he stood by the Del Mar winner's circle at the end of a sunny July 25 afternoon. With members of the Great Friends Stables, a throng of Run Fast investors, most of them fledgling fans in for $100 apiece for a share of the stable, had just witnessed Listenupshance win the $401,500 Grade 1 Bing Crosby Stakes by a nose over a relentless Maximum Bourbon and, as part of the Breeders' Cup Challenge "Win and You're In" series earn a fees-paid berth for the Cygames Breeders' Cup Sprint Oct. 31 at Keeneland.

In taking the Crosby, Listenupshance confirmed the form he displayed at Saratoga Race Course in early June at the end of the 6 1/2-furlong Grade 3 True North Stakes when he was lapped on sprint division leaders Book'em Danno  and Bentornato.

With its mixed bag of proven veterans such as Dr. Venkman and Stronghold, along with favored Cornucopian, easy winner of the San Carlos Stakes in his most recent California start, the race could have gone a number of ways.

"I'm just hoping for a lot of them to go, and we come with a good run that sets us up for races later on," said Peter Miller, who sent forth Moonlight, the longest shot in the field at 47-1.

Listenupshance won the 2026 Bing Crosby Stakes. (Eclipse Sportswire)

Miller got his wish, as the invader Mad House and Sonny Leon—making his Del Mar debut—tore off quickly from the gate to lead through an opening quarter in :21.88.

He was not alone. In the True North, Listenupshance broke poorly and rushed up to challenge for the pace. This time, he left the gate like a pro for Emisael Jaramillo and set up shop alongside Mad House, while Cornucopian and Maximum Bourbon stalked within range.

Listenupshance edged to the front turning for home, although Mad House refused to go quietly, and Maximum Bourbon began to roll.

Inside the final furlong, the daylight enjoyed by Listenupshance began to disappear, but he had just enough to put his dark brown nose on the wire first, stopping the timer in 1:09.33. Just as Miller had hoped, Moonlight came flying late to finish third, a length in front of Mad House.

Unfortunately, Cornucopian was pulled up on the turn by Juan Hernandez, who felt the colt go wrong in an ankle. The son of Into Mischief, a $1.1 million yearling, was vanned off for evaluation.

Doug O'Neill trains Listenupshance, a 4-year-old son of Shancelot out of the Hard Spun  mare Listenupnow. The trainer has been at this level before with exciting sprinters—most famously 2006 Breeders' Cup Sprint winner Thor's Echo —but in Kluger and his army of $100 investors, O'Neill might have a tiger by the tail.

Kluger, 40, manages talents such as Lil Yachty and Lil Wayne.

"I got arrested when I was underage because I kept going back and betting at a Tampa Bay greyhound track," Kluger said. "I became a horse owner about six years ago. I couldn't figure out why horse racing had such a negative connotation with young people. It's been my goal to make it more accessible to everyone, and to let people enjoy the vanity of the sport. For their $100, they get the thrill of the experience and none of the hassle. And, on a day like this, there's champagne, and a trip to the Breeders' Cup."