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.
About The Author
Gabriel Bras Nevares is a music and pop culture news writer for HotNewHipHop. He started in 2022 as a weekend writer and, since joining the team full-time, has developed a strong knowledge in hip-hop news and releases. Whether it’s regular coverage or occasional interviews and album reviews, he continues to search for the most relevant news for his audience and find the best new releases in the genre. What excites him the most is finding pop culture stories of interest, as well as a deeper passion for the art form of hip-hop and its contemporary output.
Specifically, Gabriel enjoys the fringes of rap music: the experimental, boundary-pushing, and raw alternatives to the mainstream sound. As a proud native of San Juan, Puerto Rico, he also stays up-to-date with the archipelago’s local scene and its biggest musical exponents in reggaetón, salsa, indie, and beyond.
Before working at HotNewHipHop, Gabriel produced multiple short documentaries, artist interviews, venue spotlights, and audio podcasts on a variety of genres and musical figures. Hardcore punk and Go-go music defined much of his coverage during his time at the George Washington University in D.C.
His favorite hip-hop artists working today are Tyler, The Creator, Boldy James, JPEGMAFIA, and Earl Sweatshirt.
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