I think it's a close decision in favor of Trinidad, mostly due to the size and youth of Tito. Past prime Whitaker didn't really do that bad against Tito. He gave a good account of himself considering he was on coke already, and coming off a long layoff.
I think this one is pretty tough to call. Although Whitaker was the better/greater fighter than Trinidad, he’s also naturally smaller, having peaked at 135 (or arguably during his short stay at 140). Whitaker was about 4-5 inches shorter and giving up 4 inches in wingspan. Trinidad wasn’t as in love with his power back in 1995 as he was in 2001. I thought his best boxing performance was against Oba Carr, and that was in late 94’. He patiently and cleverly picked his shots well and broke him down. 1995 was Whitaker’s last year before he really started declining. Trinidad had a much better straight right hand than Oscar did, so he would have more success with that punch than Oscar did against Pea when he kept connecting with the air. Still, the footwork be a key. Tito was always somewhat flat footed, while Whitaker had among the best footwork and use of angles of any boxer ever. Whitaker could place himself in positions to land and make it so difficult to get hit in return. He would obviously want to win the battle of where to position their lead foot. I think Whitaker would land shots to win a decision, but it wouldn’t be easy.
I'd lean towards Whitaker in 1993 and 1994 but I think Whitaker had slipped a bit by 1995 - not a huge amount but enough for the balance to tip in Tito's favour.
Whitaker seems to have been sitting down more on his punches and punching harder circa '95, but I think he was losing some of his elusiveness by then. I think we see a much closer fight than their actual meeting, it's just hard to figure who comes out on top in the end.
When Tyson got out in 95’, Tito had a take a backseat, and King underpromoted him. 95-98 were kind of wasted years for him. It looks here like they were in discussion for a fight to take place in 96’, but it fell apart. I don’t remember the specifics but I’m guessing it had something to do with Don King and Dan Duva. I think Whitaker would have prepared better for Tito than he did for Rivera, but still, I don’t know if Whitaker had enough in 96’. 95’ may have been the last year Pea would win, and I’m not overly confident about that either. https://www.latimes.com/archives/la-xpm-1995-11-19-sp-5134-story.html?_amp=true
I think Tito is a difficult task for any Whitaker. I don't think he'd ever get much offense off, although obviously if you transported the fight back to 1992, you'd probably have to favour Whitaker at that point. I'd still take Tito in 95 though.
