This is good stuff because some of these fights end in ways that might surprise some.
Felix Trinidad vs The Following
Ray Leonard: This fight would be rather easy for Leonard. Sugar Ray possesses Everything that troubles Trinidad. Tito has one VERY Clear weakness. He doesn't know how to move laterally. Remember how Oscar made Felix look like a fool, only to get robbed? Everything Oscar can do, Sugar can do Better..............and Faster........and Harder.........and Smarter........
Leonard by KO in 9
Henry Armstrong: For the next Thousand years, Armstrong will always rank higher than Trinidad. He might always be ranked in the Top 5 at welterweight..........But I'm not so sure he beats Trinidad. You MUST consider two things. Trinidad's lateral movement sucks. But he wouldn't need it against Armstrong, who would come right at him. For all his illustrious work at 147, Armstrong only stands 5'5.5". Much is made of his fight with Ray Robinson but Armstrong's style would ill suit him for an aggressive bomber like Trinidad because he is also very aggressive. His aggression just might work against him as he plays right into Trinidad's hands. I'll always agree that Armstrong is the greater fighter. Call me crazy but I'm not convinced that he would always beat Trinidad. Too much height. Too much aggression. Too much power. Ask me tomorrow and it might be different. I can tell you that Armstrong doesn't win every time. He doesn't win today either.
Trinidad by KO in 10.
Mickey Walker: Again, Armstrong ranks higher against a fighter he's not guaranteed to beat. The difference here is that Trinidad would hit Walker easily. But he wouldn't slow him down. See, the difference is that Walker is clearly stronger than Armstrong and he would survive enough of Tito's early bombs to get inside and take away Tito's range and power.
Walker by KO in 12
Manny Pacquiao: Great fight. Some can see Pacquiao chopping Trinidad down like he did to Margarito. However, the problem is that Trinidad is always throwing punches. If you hit him hard enough to KO him, he will throw 4 punches before he hits the canvas. Pacquiao's size and aggression works against him.
Trinidad by KO in 8
Joe Walcott: Smaller size and better skill actually works against Walcott. He lacks the height or foot work to stop Tito from doing what he does best.
Trinidad by KO in 11
Carmen Basilio: Basilio is Brick Wall Tough but he is too limited in style and athletics. There is no way he would take as many shots from Tito and remain standing. He simply lacks the ability to stop Tito or return fire. It could be a struggle for Tito at 147 but I still see him winning this.
Trinidad by KO in 9
Jimmy McLarnin: McLarnin has one clear problem. He doesn't punch hard enough to keep Trinidad from drilling left hooks and right hands through his face.
Armstrong by TKO in 8.
Jose Napoles: Napoles is slick enough to keep Tito off balance all night. Tito could catch and finish him but that's unlikely
Wilfred Benitez: Both were at their respective best at 154 but Benitez would nullify Tito's power and pitch a near shutout.
Terry Norris: Norris has a lot of talent but, like Trinidad, he doesn't adjust well to change. Norris would box Tito's ears off for the first 8 rounds. The problem is that Trinidad would never give up and Norris would make at least one mistake along the way. That's all it would take.
Trinidad by KO in 12
Bob Fitzsimmons: FAR too old. Fitz' style is simply too outdated. There is no way he beats any top level modern middleweight. He's probably tougher than all of them but can't outbox any of them.
Freddie Steele: Steele is tough but he has none of the tools or gifts to expose Trinidad's weaknesses. Trinidad is a very correct boxer. He lacks any speed but wouldn't need it against Steele.
Trinidad W 15.