Tito got KDed by his opponents many times but he came back to knock them out. Hopkins was another case though.
Most people will completely dismiss Pacquiao but there are plenty of things he does that would give Trinidad a lot of problems. His speed of foot (and hand) would give Trinidad absolute hell, you can bet Pacquiao wouldn't be dicking around being complacent in this matchup like he has been against Cotto and Clottey. Roach isn't an idiot and he would shamelessly advise Pacquiao to climb aboard a bicycle for this matchup, particularly with the Oscar matchup showing Tito's glaring weakness to good movement. Pacquiao probably gets stopped or at least dominated until the final bell starting around the 8th round. He gets timed coming in after winning a number of the early rounds (probably even ahead on the cards) after giving Trinidad a lot of trouble with his movement. To be honest i wouldn't be surprised if Manny won this fight though. I don't rate Tito as much as most, i would give Mayweather a very good shot as well.
Pacman would probably lose this one. Pacman's gets hit too much for Tito. Tito's left hook would be too strong, even if it didn't land clean.
Zero chance. Pacquiao is too small for a prime power Trinidad. Trinidad only lost to fighters that were bigger and stronger then him. Pacquiao don't have the defense like a prime Hopkins and a prime Wright. But at welterweight Trinidad is undefeated. If they would have fought, a prime Trinidad would destroyed Pacquiao badly.
With or without illegal handwraps? I can see Pac using his footspeed and boxing circles around Tito. Tito couldnt do a thing when DLH decided to dance around him, Pac is a hell lot faster than DLH on his feet.
I think he won't lose badly as you believe. Pac's unorthodox style, speed, and movement, and having Roach at his side would definitely give him a good chance to also land his bombs against Trinidad.
But what does the size have to do with it? Pac obv hits hard, obviously can take a punch though I'm sure he wont wanna rope-a-dope Tito and on top of that, he has the advantages of a smaller man. He's a lot faster and more agile. Tito has a very typical boxer style, methodical, if Pac fights a very good fight and circles and keep away from Tito all night just using speed and angles to score points, he may wide UD him. That said, if tito catches him with a big one, good night.
Im sorry, I'd have to go with Trinidad on this one. Even though he'd be outboxed and maybe even hit the deck, once that left touches Manny(which it likely would) its lights out.