While two weeks remain until the first anniversary of his momentous loss to Terence Crawford, Canelo Alvarez is busy preparing for his comeback fight, which is now two months away. He is scheduled to face WBC super middleweight champion Christian Mbilli on a card promoted by his Canelo Promotions and broadcast on DAZN in Riyadh, Saudi Arabia, on October 31.

Sidelined by the defeat to Crawford and subsequent elbow surgery, Canelo finds himself in the spotlight once again. As he gears up for the final leg of his outstanding career, anecdotes from the Mexican star’s life are also getting renewed attention. A recent development saw Ring Magazine share an old video in which Canelo reflected on the time when rap icon Jay-Z lost a hefty sum betting against him.

“He (Jay-Z) lost. Bad bet,” Canelo told Complex’s Speedy Morman a year ago. “I don’t care if it’s Jay-Z or whoever… I don’t give a f–k.”

His comments came after the host highlighted how Jay-Z had wagered $250,000 on Canelo to lose against the Puerto Rican heavy-hitter Miguel Cotto in their 2015 bout.

Fighting for the Ring and WBC middleweight title, the bout took place on November 21, 2015, at Nevada’s Mandalay Bay Events Center. The fight went the distance, with Canelo defeating Cotto by unanimous decision.

The matchup came two years after Canelo suffered his first career loss to Floyd Mayweather. Coming off that defeat and stepping up to challenge for his first major title, Canelo may have appeared vulnerable to some, including Jay-Z.

What added intrigue to the situation was that reports such as the one from CBS initially suggested the bet was for $100,000.

The wager was between Canelo’s then-promoter Oscar De La Hoya and Jay-Z, who, through his sports agency, Roc Nation Sports, handled Cotto.

If Cotto won, De La Hoya would donate $100,000 to the Shawn Carter Foundation. However, if Canelo won, Jay Z would donate $100,000 to the White Memorial Medical Center cancer unit. With the Mexican eventually winning, reports later revealed Jay-Z paid up his part of the deal by wiring the figure to the Los Angeles hospital.

The $250,000 figure, however, remained disputed. Initially, reports said the wager involved $100k. De La Hoya also seems to have said at the time: “I don’t imagine (Jay’s) excited about losing $100,000, but he can take some comfort in knowing that it’s going to a good cause.”

However, years later, in a 2024 interview with Shannon Sharpe on the Club Shay Shay podcast, De la Hoya stated, “So I said, ‘You know what? Why don’t you place a bet here of $250,000? But it goes to charity.”

That discrepancy, however, had no impact on Canelo. The win over Cotto sparked a run that continued till Dmitry Bivol ended the Mexican’s twelve-fight winning streak. Even so, Canelo rebounded from the upset to continue his reign as undisputed champion at 168 pounds until Crawford defeated him.

That history helps explain why, even with several prominent figures putting their money on his opponents, Canelo remains unperturbed, confident that he will succeed.

When Jay-Z finally got it right against Canelo Alvarez

Unfortunately, two days after he gave that interview, Canelo suffered a setback when Crawford took him to the cleaners, in what many viewed as a one-sided affair that exposed the Mexican against the sublime skills of the Nebraskan switch-hitter.

Intriguingly, some reports suggested that Jay-Z wasn’t unlucky this time betting against Canelo. He allegedly bet $500,000 on Crawford, taking home $1.2 million after Crawford secured the win.

The rapper wasn’t the only individual who seemingly won a wager against Canelo. According to some social media reports, his former opponent Floyd Mayweather also earned $124,000 after placing a $50,000 bet on Crawford. Though not disclosing exact figures, action-star Jason Statham also mentioned that he had put “big money” on Crawford to pull off a historic win.

One person who seemingly lost a bet by backing Canelo to defeat Crawford appears to be Drake. Like Mayweather, the Canadian rapper also wagered $50,000 on the Mexican to hand Crawford the first professional loss of his career. Drake reportedly lost after Crawford secured the victory.

Beyond the money, what is more significant here is whether Canelo comes through on his word and defeats Mbilli when they meet in Riyadh, unfazed by what others think, and writes a new chapter in what could be the final few fights of his career.