Trinidad has wins over De la Hoya Vargas Whitaker Mayorga Reid Joppy Assuming Cotto beats the golden and pretty boy Mayweather De la Hoya Mosely Judah Malignaggi Quintana Trinidad's longevity will still give him the edge.
Cotto might get better than Tito in accomplishments, but Tito will always will have more fans (though that doesn't matter when making boxing rankings). Tito's win over De la Hoya was a robbery, possibly the biggest in history.
Tito and Cotto are completely different fighters and Cotto has a more complete skill set. Cotto is just 26 and on the verge of fighting the biggest fights of his career and the sport in 2008, so he might be a step ahead of Tito timewise. Tito held titles in three different weightclasses, a ton of defences at WW, incredible at 154, he lost twice to certififeed HOF boxers at midleweight. Should Tito beat Roy Jones that will add to his legacy, even though Jones is old he is expected to win and is the clear betting favorite. So Cotto still has a lot of work to do, but he is well on his way to equaling Tito's status if not surpassing him. A loss to De La Hoya takes him out of the discussion though. A W against DLH and PBF he surpasses Tito.
That was a really close fight and I am sick and tired of people just assuming that Oscar was robbed in that fight, the early rounds were all DLH the middle rounds were close and could have gone either way then Tito chased his ass for four rounds landing some heavy shots while he ran. They were both title holders and Tito did his part to fight like a champ. For god's sake Oscar even admits that he should have never fought the way he did.
Trinidad cleaned out 147 and 154. Cotto has a ways to go. Trinidad at 26 had already defended the Welterweight title 16 times and on his way to moving up in weight.
I wouldn't go quite that far Tyrone Everett vs. Alfredo Escalera Pernell Whitaker vs. Jose Luis Ramirez I Both were much bigger robberies
If he beat Mayweather, De La Hoya and mabye a couple of other top welters convicingly. I could give him it.