Jay-Z doesn't just honor a bet, he honors it on the spot.
In an appearance on Shannon Sharpe's Club Shay Shay podcast, boxing promoter Oscar De La Hoya spoke about the time Jay-Z lost a bet to him over a fight between Canelo Alvarez and Miguel Cotto in 2015. "So we're promoting Canelo at the time, Golden Boy, and he's promoting Cotto," said De La Hoya after being asked about the bet.
"So I said, 'You know what? Why don't place a bet here of $250,000? But it goes to charity," he continued. "So Canelo wins, my charity wins the two-fifths, and sure enough he paid it on the spot. I think the next day the cheque was in the bank. Jay-Z loves boxing, he knows his boxing. But he's a guy who pays his bets."
Sharpe suggested he "took advantage" of Jay-Z, but De La Hoya insisted that it was a close fight. "But I had the insight, so," he laughed. At the time of the fight, Alvarez was represented by De La Hoya's Golden Boy Promotions, while Jay-Z's Roc Nation Sports represented Cotto.
Alvarez won via 12-round unanimous decision, but Hov made sure to congratulate his client after the fight. "You fought a great fight, man," he told Cotto.
In 2015, TMZ reported Jay-Z paid $100,000 after losing his bet. Either De La Hoya is misremembering the amount or Hov forked over the rest in private.