10 years ago, I would have said Nunn easily. Now, I'm not sure. Michael Nunn and Aaron Pryor are two fighters I came down to Earth on. I suppose the 88 Nunn beats the 87 Leonard, but I sure as Hell am not certain about it. I could see Ray pulling out a close one on intangibles alone. Nunn, slight favorite.
I think Nunn could be a bad style matchup for an aging Leonard. I don't think Leonard would have the power or strength to fluster Nunn and offset his physical advantages. In fact, I think Leonard matches up with Nunn similar to how Kalamby did, although I wouldn't expect Leonard to be KO'd in that manner.