LOS ANGELES, CALIFORNIA – FEBRUARY 28: Jay-Z attends a basketball game between the Los Angeles Clippers and the Los Angeles Lakers at Crypto.com Arena on February 28, 2024 in Los Angeles, California. (Photo by Allen Berezovsky/Getty Images)

The boxing legend characterized Jay-Z as “a man who pays his bets.” Fortunately, there’s no love lost here, as it all went to charity.

Jay-Z is a big sports fan, as evidenced these days by his infamous connection to the NFL and his role in their Super Bowl halftime shows. But the connection stretches much further back, and it’s not completely dominated by wins for the East Coast legend. Moreover, Oscar De La Hoya recently told Shannon Sharpe on his Club Shay Shay program that Hov lost a six-figure bet to him almost a decade ago, and paid it honorably. The boxing legend was promoting Canelo Alvarez in his November 2015 fight against Miguel Cotto, who benefitted from the Roc Nation boss’ financial backing… But not in the match.

“So we’re promoting Canelo at the time, Golden Boy, and [Jay-Z’s] promoting Cotto,” Oscar De La Hoya recalled. “So I said, ‘You know what? Why don’t place a bet here of $250,000? But it goes to charity.’ So Canelo wins, my charity wins the two-fifths, and sure enough he paid it on the spot. I think the next day, the check was in the bank. Jay-Z loves boxing, he knows his boxing. But he’s a guy who pays his bets.”

Oscar De La Hoya Recalls Him & Jay-Z’s 2015 Bet

However, there’s a bit of a conflicting report on the nature of this bet, as TMZ alleged back in 2015 that Jay-Z actually lost a $100,000 bet, not one for a quarter of a million. “Thanks to Jay-Z, thousands of patients at White Memorial Medical Center will also be winners,” Oscar De La Hoya remarked at the time. “I don’t imagine [he’s] excited about losing $100,000, but he can take some comfort in knowing that it’s going to a good cause.” As far as his recent exploits in the boxing world, Oscar is looking forward to a healthy Mike Tyson performance against Jake Paul.

Meanwhile, Jay-Z recently stirred up a storm thanks to his reclaiming of Dame Dash’s Reasonable Doubt shares. Well, not right now, as he would eventually earn this back from Dame in a couple of years. He’s not too happy about the situation at all, but it seems like his former co-boss is dead-set on getting his shares back. We’ll see what happens with that situation, and whether or not it will turn out to be a losing bet.