I think the middleweight Benn was too crude for Duran. Duran would no doubt have to survive some scary moments early, but the gap in skill and intelligence is too big. Duran wears him down, and counters him until a tiring Benn gets stopped late. But that's just Benn. I think McClellan and Jackson would have been very bad matchups for Duran and would have KO'd ole Bobby.
I think he could. Think about it... would you pick Benn to beat the Duran that slaughtered Moore? I sure as Hell wouldn't. I don't see a reason why that version of Duran couldn't come in a trim 157 and school Benn.
Duran would have defeated Benn, climbed off the canvas to do so perhaps, but would have stopped Benn late.
The Hagler Duran wins by late KO or decision The time in which they sparred, Duran wins by DQ after Benn illegally hits Duran after scoring a KD