Sugar Ray Leonard Sends Terence Crawford Message On Beating Canelo Alvarez

If you were to ask a boxing fan who the greatest boxer of all time is, you would get plenty of responses saying Sugar Ray Leonard.
This legend of the sweet science won world titles in five weight classes, was the lineal champion in three weight classes, and secured a gold medal as an amateur at the 1976 Summer Olympics. Not to mention that he fought all the best boxers of his era who were around his weight.
Leonard is still around the sport of boxing, and his thoughts and wisdom are considered gospel among the community, considering all that he has accomplished. This is why it's wise for people to listen whenever he offers an opinion about an upcoming fight.
Of course, there are no bigger fights on the boxing calendar than the mid-September showdown between pound-for-pound greats Canelo Alvarez and Terence Crawford.
Canelo Álvarez vs Terence Crawford stat breakdown 📊
— Source of Boxing (@Sourceofboxing) May 19, 2025
Who wins this❔ pic.twitter.com/SzGQRpBOg1
While Crawford is one of the world's most technical boxers, the fact that he's moving up several weight classes in order to fight Canelo is typically viewed as the most likely reason he'll come up short against the Mexican superstar.
Sugar Ray Leonard addressed this sentiment during a May 22 interview with FightHub TV. When he was asked about Canelo potentially being too big of a fighter for Crawford, Leonard said:
"I mean, that's true. But you know what? There's always a way. There's always a way. There's always a way to win."
Given that Sugar Ray found success in three different weight classes, he would know better than just about everybody else that victory against Canelo is possible for the smaller Crawford.
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Grant Young is a Staff Writer for On SI’s Boxing, New York Mets, Indiana Fever, and Women’s Fastbreak sites. Before joining SI in 2024, he wrote for various boxing and sports verticals such as FanBuzz and NY Fights. Young has a bachelor’s degree in marketing and a master’s degree in creative writing with an emphasis on sports nonfiction from the University of San Francisco, where he played five seasons of Division 1 baseball. He fought Muay Thai professionally in Thailand in 2023, loves a good essay, and is driven crazy trying to handle a pitpull puppy named Aura. Young lives in San Diego and was raised in the San Francisco Bay Area.