Although it seems crazy to say it, I actually think Benn may have had a good chance to win this. Post Hagler, Leonard was knocked down in every fight he had, apart from the Duran fight. Against Benn, I can't imagine SRL not getting hit solidly at some point..which means he's going down. Tough one.
I think it depends when it takes place. The Benn of the Watson fight, May 89 loses to the Leonard of the Hearns 2 fight, June 89. The same reason he lost to Watson. If Watson could handle Benn's Kamikaze style of that fight I'm sure Leonard would of too. Benn after that fight with a lesson learned and a few more fights under his belt could make things a bit more interesting.
I dont think this is he kind of guy leonard would want to fight. It's no wonder whey he decided against defending his WBC title and opting for Lalonde. There wasn't too many middleweight contenders considered safe enough for him. And forget Micheal Nunn-that fight wasnt coming off no matter what!