Sugar Ray in the 1940s welter scene

He’d be competitive but not sure a bloke with only 40 fights could handle fighting 20 times a year. I’d say he possibly loses to a few in that era - including post 1940 Armstrong, LaMotta and Gavilan.

Can’t see him getting the better of SRR at all throughout the 40s. Just my opinion of course and IDKSAB.

 

Robi moved up to middle in the 50`s and I feel Leonard would have had problems with LaMotta`s lead hand at 160, Fullmer would have bothered him and Bobo, Turpin may have beaten Leonard. Gavilan might have beaten Leoard at 147 but he lacked power like Mayweather Sr who was overpowered by Leonard after giving him problems, Basilio would have done well v Leonard at 147 and 160. Robinson`s counter combo`s probably would give him the edge over Leonard.

 

I don't know, but it would be hard to see. This is where his mentality might fail him. He was a guy who could motivate more for big big fights, but for a long career with 100 fights? I don't know if he loved boxing as much as the competition. He needed the special motivation to get up for fights. I could see Hearns or Duran or Hagler do that more, but not Ray. He could outfight those guys in the 4 times he won the fights, and give a good showing in the other two and with Benitez, but he didn't look like he had the fight in him for a long career. Even in the 1980s he didn't. Although he did fight amateur and he had 150 or so fights. But that is different than the pros with hungry guys who are out there for a paycheck in a tough era. Skillwise he could beat anyone. Robinson would be a guy who would be tough for him to beat.

 

He'd beat anyone not named Robinson and would give Robinson all he could handle and maybe beat him too.

 

Ray Leonard would have his hands full with Kid Gavilan. Fritzie Zivac is an ugly fight. George Costner would be a threat but Costner's chin may get in the way. Tommy Bell? A rough nite but RL should be him. The ? That is out there is how would he respond having to fight all these type of opponents 2-3 times. Durability, hands? His eyes?

I don't think he could do what Robinson did in that division. SRR put it on lockdown like nobody before or since. RL would catch a few Ls along the way even as a standout.

 

If Leonard fought during that era, he would be just as dynamic. It would mean he would've
been born in the 20's. Would not have the bright light of a Olympic Gold Medal and mass
media attention. But if he had the physical ability and skills he had late 70's early 80's
with the mental toughness of men usually born of that era , Who beats him outside of
the original Sugar Ray? Nobody.

 

Robinson was a bit better in every department

 

If you meant 1 / 5 fights maybe

 

You would count Gavilan out vs Leonard?

You would literally walk into The Keed's dressing room before the fight looking him square in the eye and say 'you can't win!
That's rough.

 

Love Gavilan. No doubt it would've been a heck of a fight.
But Leonard beats him in my opinion. The only fighter I've
seen at welter that beats Sugar Ray Leonard is Sugar Ray Robinson.
And Robinson would be in for a heck of a fight!

 

I think Hearns could have beat Ray in a rematch, Ray got lucky hurting Hearns after being out-boxed, Tommy was more skilled than Ray but sugar was faster and he managed to hurt Hearns then walk him down.

 

I feel Leonard had quicker hands and a better reach.

 

Maybe he could've or maybe he gets stopped earlier,
the usual results of a 2nd fight between prime vs prime fighters . Leonard was a better
welterweight prime vs prime. Their was nothing "lucky"
about his victory. And he exposed a weakness in Hearns
that would be exploited by other fighters specifically Hagler
and Barkley. Work his body, make him use his legs.
fight him.