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Fantasy Boxing Matchup: Sugar Ray Robinson vs Sugar Ray Leonard

Two Sugar Rays, two different eras for boxing. Who wins head-to-head?

Photos by Hulton Archive/Getty Images and Getty Images

OK, we’ve played around here for the first few entries in this series. Marciano-Tyson, Mayweather-Chavez, Jones-Foster, Pacquiao-Hamed. Interesting ideas to varying degrees, sure, maybe some great fights in there, but none of those big bangers you think of when you think “dream matchup.”

For one thing, we’re gonna have to fill a lot of time with these, as it’s looking more and more like boxing isn’t coming back until July. So I don’t wanna burn all the mega-dream matches early.

But today, we get into one of those.


That’s right.

It’s the Battle of the Sugar Rays.

Sugar Ray Robinson vs Sugar Ray Leonard

Both of these guys fought in various divisions of their Hall of Fame careers, of course. Robinson fought between 135 and 175 from 1940-1965, and Leonard fought between 147 and “175” between 1977 and 1997, which is really 1977 and 1991, as his final fight was a bad idea comeback that resulted in his only stoppage loss.

(As for that “175,” that was his 1988 fight with Donny Lalonde, where Leonard weighed in at 165, Lalonde at 167, and they fought for both Lalonde’s WBC light heavyweight title and the vacant WBC super middleweight title. Leonard won. In Robinson’s lone fight as a light heavyweight, he weighed in just over 157 pounds to fight champ Joey Maxim, who was at 173, at Yankee Stadium in 1952. Robinson was winning the fight widely on the cards, but the heat was overwhelming and he retired after the 13th round because of it.)

But for the purposes of this dream bout scenario, we’re saying they’re fighting at 147 pounds, which is where both may well have been at their very best; I’m sure of it with Leonard, but Robinson’s results make arguments that he was every bit as good at middleweight.

This isn’t one where I think I need to go on too much. Everyone knows the legend of Sugar Ray Robinson, who went 174-19-6 (109 KO) in an era boldly different from the modern times where a loss is a monstrous setback and if you take one, we might see you six or nine or 12 months later as you get time to fine-tune what went wrong. I mean, when Robinson lost a decision to Jake LaMotta in 1943 — where Lamotta was a middleweight and Robinson a welterweight — he was back in the ring two weeks later and beat California Jackie Wilson, a legit welterweight, at Madison Square Garden.

But despite the losses, it has long been accepted that Ray Robinson is either the greatest pound-for-pound fighter to ever live, or at the very, very least, you cannot have the discussion seriously without including his name. There is not a boxer from his time or since that does not see Robinson in that light.

Leonard, who had a career record of 36-3-1 (25 KO), is by contrast the poster boy for a well-managed career in the early stages of what we’ve seen boxing become in the last 40 years. On the whole, it’s a good thing, with more money for the fighters and better conditions in the game overall.

And this is not to say that Leonard was handled with baby gloves forever. He was a gold medalist at the Montreal Olympics in 1976, and he was getting in with some decent knockaround guy sorts early in his pro career. By 1979, he was in with the big dogs, beating Wilfred Benitez (who was great) for the WBC welterweight title, and once the 80s rolled around, he became one of the “Four Kings” of the decade, alongside Roberto Duran, Thomas Hearns, and Marvin Hagler. They all fought each other.

Robinson’s record speaks for itself. It’s too long and full of highlights to really dig into without going on too long, and I’ve already gone on longer than I set out to, really, because just talking about these guys at all gets me excited.

So let’s settle it. 147 pounds, Robinson vs Leonard. We’re warping them into a shared existence via some sort of time traveling device here, so just assume they bought know how to fight a 12-round distance and their weigh-in was fine on whatever fantasy day it took place.


Who wins, Sugar Ray or Sugar Ray?

This poll is closed

  • 78%
    Sugar Ray Robinson
    (567 votes)
  • 21%
    Sugar Ray Leonard
    (157 votes)
724 votes total Vote Now

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