I believe Pernell Whitaker would of beat Roberto Duran, you say his early fights were at Lightweight. But he beat some very good pressure fighters at Lightweight Jose Luis Ramirez, Azumah Nelson, Greg Haugen.
And he beat all 3 of them pretty comfortably, even Azumah Nelson lost 8 rounds to 4 on my card. I think Roberto Duran would of been so frustrated by Pernell Whitaker's defense.
And even if Roberto Duran tried to swarm Pernell Whitaker, Pernell Whitaker had a very high workrate himself at Lightweight. Plus he had a very good chin.
As for some more fighters that could of beaten him at Lightweight.
Alexis Arguello
Shane Mosley
Floyd Mayweather Jr
ODLH
And maybe a prime Hector Camacho, although that might be reaching.


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