Ok...What's the "REAL REASON" not speculation, But the "Real Reason" why...

oscar flew to puerto rico and tried.

at one point it was going to happen.. but tito couldn't lose the weight.

 

1) Who was at fault for it not Happening?
Tito fans say Oscar, Oscar fans say Tito. The original reason for not happening was the size of the purse. Oscar was still ending up with the bigger purse though he "lost" the first fight. Later on weight becomes an issue.


2) What was the best "year" for it to happen...if it did?
I guess after 1999, 2001 was the time they were in the same division at the same time. Tito was collecting belts though and Oscar was still wet behind the ears at 154. Tito jumps weight again soon after.

3) What weight would it have happened at...Especially since both began to move up later in their careers?

158 or so, that's the best scenerio. But DLH got knocked out at such a weight and swore off climbing above 154 again, therein likes the problem.

4) Who WINS?

I seriously believe Oscar would have won, unless the fight took place at 147 right after the first fight, then Tito would have knocked Oscar out. The reason is Oscar left that first fight wanting to war with everyone, thinking he wasn't entertaining enough. This cost him the first Mosley fight as well. So it's safe to say Trinidad wouldn't have fought the boxer he fought in the first fight but the same DLH that showed up against Mosley.

Who knows though, conventional wisdom has Tito knocking everyone out in a war. But you never know if Hoya would come out on top.

 

Because his wife is Puerto Rican and he said he would never fight another Puerto Rican.

 

Bob Arum talked about that fight a while back before Mayweather-Pacquiao negotiations hit the fan and he said that him and Don King started arguing about stupid **** and that is why it didn't happen.

 

With Bob Arum and Don King in charge, I'm amazed that the first fight happened, to be honest.....

 

The weight was the reason why in the end..tito couldnt cut the weight when he got older...he was either too lazy or his body just couldnt..i believe he was lazy though..when he fought rjj at 170 he came in at 171 on the first try i believe and had plenty of visual body fat

 

This is the case, more or less.

 

....the weight thing is true... but it should have still happened right after the first fight.

 

Tito's father always stated the fight would happen but with the names on the contract interchanged, meaning Tito would receive the bigger purse this time as agreed on the contract from the previous fight. Well, we all know how Oscar goes & he didn't want to agree to those terms later on. Oscar didn't show up for a meeting in NYC with Tito's team, and then, that's when Sr. Trinidad said Oscar's bus had left & if he wanted to fight he would have to follow Tito & go up in weight. We all know what happened... Oscar never even dared to mention Trinidad's name and instead chose to go after Tito's leftovers from Vargas, Campas (quite disgraceful for DLH, I should say), Mayorga & even tried Hopkins, among others. Good try Oscar!

 

:yep

 

Very simplistic one sided view.
Trinidad was always the bigger man established at the higher weights. Already an established presence at welterweight way before Hoya even showed up. Even their fight was Trinidad's last fight there. Vargas a leftover? The Vargas/DLH fight was a unification match. To think a fighter is actually trying to follow in another fighter's path, taking their "leftovers" is ridiculous. I'll stick to my view which actually takes into account BOTH fighters' timelines.

Also Tito should have fought DLH. Even a smaller percentage than DLH would have guarenteed him more money than ANY of his fights post DLH. He's gonna kick himself in the future when he finds himself making commercials in Puerto Rico to sell used cars or something.

 

The real reason it never happened may have been lack of public demand. The first fight was among the biggest in boxing history, but turned out to be a complete dud (to most people...I thought it was a pretty good technical war) so the public wasn't clamoring for a second fight. This is all speculation on my part, but if there was more demand for a part II, then I don't see why it wouldn't have happened.

 

The demand was there. You are talking the whole island of Puerto Rico alone buying this fight, and then there's the DLH factor, and then there's the controversy of the first fight. This fight would have been the biggest in history, towards the end though I see your point, would have been two has beens.