As the first Sunday of May approaches, anticipation is building in the horse racing world for the Kentucky Derby 2024. But in Louisville, the excitement isn’t just about the racing; it’s also about the iconic Barnstable Brown Kentucky Derby Eve Gala, an event that draws in celebrities from far and wide.

Now in its 35th year, the Barnstable Brown Gala is also a fundraiser for a cause close to the hearts of its founders, Patricia Barnstable Brown and her late sister Priscilla Barnstable, along with their mother, Wilma. The event benefits UK HealthCare’s Barnstable Brown Diabetes Center, established in 2008 in memory of Patricia’s husband, David, who passed away from complications of diabetes.

A look back at how Drake’s advice cost Jack Harlow a hefty price at the Kentucky Derby

This year’s guest list is as star-studded as ever, with celebrities like Kid Rock, Tracy Morgan, Aaron Rodgers, and Sheryl Lee Ralph set to attend. Among them is Kentucky native and rap star Jack Harlow. However, Harlow’s attendance at the Kentucky Derby 2024 has a particular resonance, given his previous appearance alongside Drake at the event in 2022.

LOS ANGELES, CALIFORNIA – FEBRUARY 05: (FOR EDITORIAL USE ONLY) Jack Harlow attends the 65th GRAMMY Awards on February 05, 2023 in Los Angeles, California. (Photo by Jeff Kravitz/FilmMagic)

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Their collaboration, “Churchill Downs,” had just been released, and the two rappers were seen enjoying each other’s company in the VIP section. But, as we now know, their Derby experience came with a hefty price for Drizzy’s rap prodigy, Jack Harlow. According to Paper Magazine, appearing on The 85 South Comedy Show, Jack Harlow revealed a not-so-insignificant detail about his experience at the Kentucky Derby in 2022.

Despite the glamorous atmosphere and star-studded attendees like DJ Drama, Michael Jordan, Lewis Hamilton, and David Beckham, Harlow found himself in a predicament after deciding to follow his mentor and inspiration, Drake’s, lead in placing bets. “I did, I lost a lot of money,” Harlow admitted.

“I just told Drake I would bet what he bet, so I copied him.” While the two rappers looked like they were having the time of their lives, Harlow’s decision to mimic Champagnepapi’s bets ended up being a costly one. However, despite the financial setback, their Derby shenanigans were certainly memorable. So, who did the rapper bet on? Let’s find out.

Who did the rappers bet on that year?

In 2022, Jack Harlow and Drake brought their infectious energy to the 148th running of the Kentucky Derby. Amidst waving to fans and sharing laughs, the duo engaged in a memorable NBC Sports interview. In typical fashion, Drake even playfully interrupted Harlow’s interview, showered him with praise, and even exclaimed, “I just had to show up. I’m so proud of this guy.” As the interview progressed, they were asked if they had placed any bets on the race.

Harlow shared, “We were forced to make a move, in the one and only with Happy Jack.” Despite their enthusiasm, their bet on Happy Jack ended in disappointment as the horse finished 14th, while Rich Strike emerged victorious. With the Kentucky Derby 2024 just four days away and an exciting lineup of horses set to compete, including Sierra Leone, Just a Touch, Dornoch, and Fierceness, fans are eagerly anticipating who Jack Harlow will bet on this year. Will he redeem himself from Drizzy’s advice in 2022? Any guesses or advice for the star? Comment below!