Drake is now 0-2 on marquee fight bets in the second half of 2023. The Canadian rapper put down $500K on the UFC 293 headliner between Israel Adesayna and Sean Strickland. Specifically, Drake bet that Adesanya would beat Strickland via KO. With 1.84 odds, Drizzy would have walked away with a cool $920K if he had won. However, Strickland pulled off what many are calling the greatest upset in UFC middleweight history. While there wasn't a KO in Sydney, Strickland edged out a close fight to win by unanimous decision and take the middleweight belt. "Am I fucking dreaming? Am I going to wake up? Somebody hit me. Literally, never in a million years did I think I was going to be here. Izzy is a bad motherfucker. You don't fight a guy with that many highlight-reel KOs. I was even kind of doubting myself at times," Strickland said after the fight.
However, as mentioned, this is now Drake's second consecutive bad bet this year. Drizzy opened up strong, winning $20 million after dropping $2.5 to back Terence Crawford to beat Errol Spence Jr. Then he dropped $250,000 on Nate Diaz to beat Jake Paul, which didn't end up happening. That was actually the second time that Drake had lost money on a Jake Paul. Earlier this year, Drizzy lost $400,000 when backing Paul to beat Tommy Fury. Now Drake's adding another $500K loss to his balance sheet thanks to Strickland's massive upset.
Rematch Giving Drake A Redemption?
Even as the dust settles on the fight, Dana White is already talking rematch. "The rematch is interesting," White said. "That could be the thing, too. You go into the Pereira fight, it's such a big fight, and then you overlook Strickland? I don't know the answers to these questions, but Israel does and I'm looking forward to hearing them." At this point, it's tradition to give stars like Adesanya the chance to win their belt back. After all, Strickland was simply meant to be an entertaining opponent for Adesanya to beat while Driscus du Plessis recovered from injury. It's likely that Adesanya will get another shot to reclaim his title before new paths are forged in the middleweight division.
"I had a different plan for this, but life throws curveballs at you," Adesanya said. "Win or lose, I wasn't going to say much anyway, but right now, I lost tonight to the better man on the night and I just want to be with people who care about me, my team, so I'm going to go do that," Adesanya said after the fight. He was gracious in defeat, lifting Strickland's arm before he left the Octagon. If there is a rematch, hopefully Drizzy can get his betting back on track.