Jack Harlow tried to keep up with Drake and his betting at the Kentucky Derby — and it didn’t work out so well for him.

HipHopDX reported that the two rappers — who collaborated on Harlow’s sophomore album on a song called, interestingly, “Churchill Downs” — went to the famous horse race earlier this month. And Harlow, being who he is, decided he’d try to keep up with the 6 God and his various bets.

Unfortunately, however, Harlow found out — the hard way — that Champagne Papi is in a class all by himself.

“I did, I lost a lot of money,” Harlow said. “I just told Drake I would bet what he bet, so I copied him.”


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Despite losing his proverbial shirt, it seemed like Harlow had a good time at the horse race while hanging out with one of the smoothest rappers in the game. He even credited Drake as being one of his Hip-Hop idols growing up.

“Drake is one of the people who literally taught me how to rap; him, Wayne, and Kanye,” he said. “Now, to be cool with him is the biggest gift. It’s better than $10 million. There’s no price tag on meeting somebody who taught you how to do it, and them saying, ‘Yo, you’re dope.’”

Betting on the Kentucky Derby, however, isn’t something that’s only done by the rich and famous. It’s actually a common occurrence, and part of the experience of the venerated horse race. So, let’s break it down a little.

Drake's Past Bets

Drake has had a bit of a gambling streak in him for quite some time, and AfroTech has reported on those bets extensively.

His predilection for betting may have something to do with his partnership with an online gambling company, Stake — but it may also be because he won so big when he placed a UFC bet worth about $275,000 in Bitcoin shortly thereafter. It was then revealed that he placed more than a million dollars in Super Bowl bets (again, in cryptocurrency) — and it paid off nicely for him. 

Unfortunately, his winning streak came to an end in April 2022, when he used Stake to bet on the NCAA Final Four — and lost his proverbial shirt.

Kentucky Derby Bets By The Numbers

Betting on the Kentucky Derby is just as much a part of the tradition as the celebrity step-and-repeats and the big, poufy hats. The Derby’s official website, in fact, breaks down what a lot of the betting looks like.

The first type of bet is called the win bet, and this is a bet that’s the most straightforward of all. Put simply, if you bet on a horse, and your horse wins, you win.

The second type of bet is called the place bet, which is something you can win if your chosen horse places in the top two of the race. That’s followed by the show bet, which is something you can win if your chosen horse places in the top three of the race.

And then there are more complicated bets, like the exotic bets (which involve multiple horses over a series of races) and the exacta bet (which involves choosing the top two horses in the exact order).

Obviously, the more complicated — and rare — a bet, the more money you win in the event of a payout.