Whitaker? I can't. Even with the briefest flashes of what he used to be, he gave Trinidad serious problems. Anyone remember how ****ign Trinidad was wrestling with him, putting him into headlocks a few seconds into the first? Stunning him with that shot in the second, Whitaker's own personal bodyshot from hell that Trinidad didn't like, bloodying his nose with his extremely accurate jabs in the first. Ah, bleh. I hate what Whitaker became when he started to erode.
Whitaker would always have problems with Trinidad, IMO. For one, Pea was best @ 135. He was a smaller guy. Tito had about 4 inches in height on Pea and a longer reach. Tito was a selective puncher with a nice straight right hand, which is always important against lefties. The guys who dominated Tito, or made him look terrible, were considerably bigger guys than Whitaker. Whitaker's best performance against a welterweight was the rematch with Buddy McGirt, who's also smaller than Tito. The other WWs that Whitaker dominated were levels below Tito. It would be a competitive fight. I say the Whitaker of 93-95 beats Tito by a close decision, but a Trinidad win wouldn't surprise me one bit.