Billionaire rapper Jay-Z once lost $250,000 to boxer Oscar De La Hoya

Jay-Z’s a moneymaker and trendsetter when the going gets tough. However, it seems he is willing to shell out the cash and spot it back too. Retired boxer Oscar De La Hoya recently recalled when Jay-Z allegedly lost a six-figure bet to him on a fight. However, he quickly settled his debt.

‘Golden Boy’ sat down with Shannon Sharpe at the ‘Club Shay Shay’ Podcast very recently. The veteran out of LA East, California has already touted his viral take on a multitude of topics. Starting from showering rare praise to old rival, Floyd Mayweather, to clashing heads with Curtis “50 Cent” Jackson on intermittent promotion issues. Now, the former champ says the stacked H.O.V. lost $250,000 on a bet to him in 2015.

So we're promoting Canelo at the time, Golden Boy, and he's promoting Cotto...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 cheque 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 via the ‘Club Shay Shay’ Podcast (@ClubShayShay)

Oscar De La Hoya rehashed details of the Miguel Cotto vs. Canelo Alvarez clash in November 2015. It saw ex-undisputed super middleweight champ Canelo come out on top as the winner. When they fought, Alvarez was represented by De La Hoya’s Golden Boy Promotions and Cotto by Jay-Z’s Roc Nation Sports. Sharpe quipped he “took advantage” of Jay-Z, but De La Hoya insisted that it was a close fight and he had an insight.

Subsequently, he said Jay was a true sport with a real love for the game and not just a payout. De La Hoya, 51, said Jay paid on the spot and there were no problems transferring a portion to charity. Now there’s a discrepancy in the six-figure bet of the unanimous 12-round bout win. De La Hoya says a quarter-million dollar payout, while TMZ Sports (@TMZ_Sports) reported that it was only a $100,000 bet. Nevertheless, he was happy about it going to a good cause.

Jay-Z and Boxing: A Tall Tale of Fanfare

In 2014, Roc Nation entered the boxing space with much bluster. Mogul Jay-Z planted his feet and flag in what he thought would be a good breeding business. Jay knew he would attract boxing talents who would enjoy the growth of their brand. However, they had to jump ship out of the boxing business partly due to the global pandemic.

A Brooklyn Nets (NBA) ownership was one thing. But the music man learned the hard way that the fractured four-belt era of pro boxing is more than just attracting talents and commission payouts. Even Oscar De La Hoya, a top bill pound for pound with $700 million in pay-per-view income used all his tactile know-how to build and struggle to make the Golden Boy Promotions last.

If those in Roc’s orbit hadn’t understood boxing is different, they understood when former WBO 160 champion Peter Quillin gave up the WBO title and suddenly veered to other opportunities with Al Haymon’s advice. However, Jay-Z kept grinding small despite the potholes. They started with a January. 9, 2015 show with Dusty Harrison v Tommy Rainone at the Madison Square Garden Theater. It ran on Fox Sports 1.

Others like Gary Shaw, Andre Ward, and Cotto came into the fold for gold. HBO Boxing, broadcasting the Cotto v Canelo affair, itself took an out after. However, Jay never lost his passion for the sport, even though he had to call quits. He later donated his boxing ring and set for The Mississippi Department of Corrections. MEMPHIS, Tenn. (WMC) for an inmate boxing program even.

In case you missed it:

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