Leonard W via wide UD. Leonard schools him & makes him look like an amateur. Unlike Oscar, he won't coast the last 4 rounds by prancing around doing nothing. Hell, he might even go for the KO victory if he has Trinidad hurt. He'll land jabs, flurries, and showboating, shoe shine combinations (like the bolo punch) to outclass the stationary Trinidad.Trinidad has little success outside of landing his left hook.
This would be a great fight. And, certainly no picnic for for Leonard. But, at his best, it is very difficult to pick against prime Leonard at Welterweight. The only fighter I am confident would beat him is his namesake from the late 40s.
Leonard turns him all night and only loses rounds he smartly decides to take off. Lopsided bout and question becomes if Ray's punches can bust up Felix. I think they do and he'd have Trinidad walking into right hands when he turns him. Hearns would be an even worse match for Felix at 147. Maybe he beats a Curry, Maybe.
He's be somewhat dangerous for a bit but Leonard is too multi faceted talented in this one. I think he'd stop him personally.