Three months. That’s all it’ll take before we find out if the scales tip the outcome or if skill still reigns supreme. Terence Crawford’s decision to jump up not one, but two weight divisions to face the two-time undisputed super middleweight champion is impossible to overlook. Equally significant is the contrast in activity. Canelo Alvarez fought and won against William Scull on May 3, while Crawford last stepped into the ring nine months and 22 days ago. Yet, for a fighter as disciplined and sharp as Bud, ring rust might be more myth than menace. The real X-factor here is the weight. And when it comes to understanding how this contrast might influence Canelo’s strategy, who better to shed light than the man who knows him best, his longtime business manager?

Long before Canelo Alvarez became the youngest boxer to win the WBC light middleweight title at age 20 in 2011, Richard Schaefer had already recognized his potential. “I started with him when he was 17 years old. I’ve known him since then and now he’s 34,” the 63-year-old former Golden Boy Promotions CEO told Ring Magazine not too long ago. Having been part of Canelo’s journey for nearly two decades, Schaefer made a bold claim ahead of the September 13 bout.

Can Terence Crawford dent Canelo Alvarez’s granite chin?

A fresh update came in yesterday from Fight Hub TV, where Richard Schaefer was asked a pointed question: “How does weight play a part in that fight?” His response was telling. “Oh, no. I don’t think that,” Schaefer said, brushing off concerns. “You saw today the guy was like I don’t know how much taller… Heightwise they are virtually the same. Crawford might even be a little bit taller. But when you look at Canelo the way he’s built, I mean his legs, his shoulders, his neck, that is why he’s never been hurt… fighting fighters at a substantially higher weight, substantially bigger than him, and they still couldn’t hurt him.”

That’s a point Canelo Alvarez has proven time and again. Take his 2023 win over John Ryder, for instance. Ryder came in two pounds heavier, but the Mexican champion dropped him in the fifth round. Go back to 2019, when the 6-feet Russian, Sergey Kovalev, fought Canelo at light heavyweight. Canelo still knocked him out in the 11th. Still, Schaefer wasn’t just there to praise Canelo Alvarez. He also pointed out what the 63-2 boxer is up against.

“And then you look at Crawford, who is a smaller guy, is moving up two weight classes. Tried at 154, barely won. Couldn’t hurt [Israil] Madrimov. Now he’s going to go against the guy with the best chin in the sport. That’s why probably oddsmakers have Canelo as a favorite,” he asserted. Yet, even with that caveat, Schaefer didn’t count the 37-year-old out entirely.

“Crawford is just a hell of a fighter. I was ringside when he fought [Errol] Spence and Spence was a hell of a fighter [too],” the business manager said. “The way he just totally neutralized Spence’s strengths was absolutely it was breathtaking to watch this. So Crawford is a very skilled fighter, very smart fighter, but again he’s never fought anybody like Canelo.”

While Canelo’s team may see little room for an upset, a boxing legend clearly disagrees. And that’s what makes this fight all the more intriguing.

Canelo Alvarez is in deep waters now

Terence Crawford currently holds the No. 3 spot on Ring Magazine’s pound-for-pound list, comfortably ahead of Canelo Alvarez, who sits further down the rankings (8th). That’s one of the reasons many believe the two division undisputed champion has the skillset to overcome the size and weight difference come fight night. Among those believers is none other than boxing legend Sugar Ray Leonard. When asked about it in a conversation with Fight Hub TV, the 1976 Olympic gold medalist didn’t shy away from offering an honest, experience-driven take.

Drawing on his own November 1988 fight against Donny Lalonde (where Leonard moved up in weight after a lengthy layoff), the Hall of Famer painted a vivid picture of what it’s like facing a bigger man in the ring. “It’s a big difference,” the five-division world champion admitted. “I mean, when I fought Donny Lalonde, every time he hit me, seriously, he hurt me to a degree—not knocking me out, but he hurt me, put it that way.” But even with that cautionary note, Sugar Ray didn’t count Crawford out.

“He can do it—I mean, he can do it, no question about that,” he said, offering a vote of confidence in the former undisputed welterweight champion. While he acknowledged the weight discrepancy as a real hurdle, Leonard’s tone was optimistic. “But you know what? There’s always a way. There’s always a way to win,” he added, with the calm assurance of someone who’s been there and done that.

So, who’s got it right? Richard Schaefer, who sees the weight and size as a mountain too steep to climb? Or Sugar Ray Leonard, who believes in Crawford’s ability to find a way?