An accomplished high school wrestler, Kermit Cintron joined the sport of boxing at the late age of 19.  Despite the late start, he still found success as an amateur, compiling a solid record of 24 wins against 3 losses. From the onset of his career, Cintron displayed freakish power, allowing him to overcome his shortcomings fundamentally as a fighter. On October 7, 2000, he made his professional debut against Jesse Williams, winning via 2nd round TKO. For nearly 4 years after that, Kermit remained undefeated and became one of the top up-and-coming prospects in the welterweight division.

On April 23, 2005, Cintron faced his toughest test when he prepared to challenge WBO welterweight champion Antonio Margarito. This was a match-up between two up-and-coming fighters looking to make a name for themselves. Unfortunately for Kermit, he proved to be no match for Margarito, suffering four knockdowns en route to a TKO loss. Suddenly, doubts about his abilities and his future began to set in from fans and critics.  Although he did find success after the loss with wins over journeymen fighters such as Jesse Feliciano and David Estrada, he was no longer considered to be one of the future stars in the sport.

Then on April 12, 2008, Kermit was given a chance to avenge his only loss and prove that he was still a force to be reckoned with in the division when he faced Margarito for a second time. Alas, the result was no different as he lost again via TKO. It quickly became evident that his physical gifts of athleticism and punching power could no longer hide his deficiencies in technique. Soon, fans and boxing analysts began to view him as a stepping stone for other up-and-coming fighter.

That was until some light was shed on Margarito with his controversial handwrap scandal that took place in his bout with Shane Mosley. Fans began to question the validity of Margarito's previous victories, including his two wins over Cintron. In fact, at one point, Kermit Cintron commented that no one had ever hit him as hard as Margarito did and the body punch that crumpled him in the second fight felt like a hammer. If Margarito's gloves were indeed loaded against Cintron, then not only did he take Cintron's undefeated record, but he also tainted his legacy as well.

Without those two loses, Cintron could very well be regarded as one of the best boxers today and he may have already gotten a chance to earn big money against fighters like Shane Mosley, Paul Williams or Miguel Cotto. He may or may not have beaten any of those fighters, but confidence can sometimes carry a fighter to new heights. At the time, a victory over a top fighter like Margarito certainly would have given him the confidence that he needed to search for bigger challenges, forcing Cintron to become more dedicated to his craft.

Some may doubt that a victory over Margarito would have catapulted Cintron to stardom, but we only have to look at the current pound-for-pound king as an example of what could have been. Remember, before the Barrera fight, Pacquiao was seen as a slugger with limited technical skills. No one really had any expectations that he would some day become a superstar. If not for the Margarito losses, who knows where Kermit Cintron might be today. In fact, as strange as it may sound, we could have been looking forward to a match between Cintron and Pacquiao in November.