The boxing legend praised Jay-Z as "a man who honors his bets," and fortunately, the outcome benefited charity. Jay-Z’s passion for sports is well-known, particularly through his connection to the NFL and involvement in Super Bowl halftime shows. However, his sports interests go back even further, and not every experience has been a win for the music mogul. Recently, Oscar De La Hoya shared on Shannon Sharpe’s Club Shay Shay program that nearly a decade ago, Jay-Z lost a significant bet to him—amounting to six figures—and paid it promptly.

De La Hoya recounted the story while promoting Canelo Alvarez's November 2015 fight against Miguel Cotto. At the time, Cotto was supported by Jay-Z's Roc Nation, while De La Hoya’s Golden Boy Promotions backed Canelo. "So we’re promoting Canelo, and [Jay-Z’s] promoting Cotto," De La Hoya explained. "I suggested a $250,000 bet, with the money going to charity.


Canelo won, so my charity received the funds, and Jay-Z paid up immediately. The next day, the check was in the bank. Jay-Z loves boxing and knows the sport well, but he’s also a man of his word."

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Interestingly, there’s some discrepancy about the bet’s amount. Back in 2015, TMZ reported that Jay-Z actually lost $100,000, not $250,000. Despite the loss, De La Hoya appreciated Jay-Z's contribution to charity, noting that "thanks to Jay-Z, thousands of patients at White Memorial Medical Center will also be winners." Although losing the bet may have stung, Jay-Z could take comfort in knowing the money went to a worthy cause.


In the meantime, De La Hoya is eager to see a healthy Mike Tyson in a potential bout against Jake Paul. On the other hand, Jay-Z recently made headlines by reclaiming his shares of Reasonable Doubt from Dame Dash.

While Dash isn’t pleased about it, it seems Jay-Z is determined to regain full control of the album’s rights. As the situation unfolds, only time will tell if this too becomes a winning move for Jay-Z.