Kimbo's last "street fight" and only lose took place in a gym against Massachusetts police officer Sean Gannon. Kimbo fans made excuses for Kimbo's loss, claiming Gannon used illegal tactics during the fight, which was a street fight where no rules were stated to begin with. The fight got enough press that Gannon was offered a one fight contract in the UFC against Brandon Lee Hinkle.
Gannon was thoroughly dominated and embarrassed during the first round of the fight, and lost via technical knock-out due to strikes. Hinkle was then later released from the UFC after losing his next two fights in a row. This raised serious questions about the actual fighting skill of Slice.
Kimbo was signed in 2007 by the new MMA promotion EliteXC. After accumulating a record of 3-0 by beating bottom of the barrel fighters like Bo Cantrell and Tank Abbott, Kimbo was supposed to face Ken Shamrock October 4th, 2008. Shamrock was on a five fight losing streak, and sadly was probably Kimbo's biggest test yet. Shamrock was forced to withdraw due to injury (cut above his eye). Kimbo reluctantly agreed to fight a much smaller and fairly unknown fighter in Seth Petruzelli, for a pay increase to $500,000. Petruzelli was a former UFC fighter and Ultimate Fighter participant, but surprisingly was immediately marked as a large underdog to Slice.
Kimbo's trainer, former UFC champion and MMA legend Bas Rutten, was interviewed later and said that he had warned Kimbo about Petruzelli's karate background and striking skill. His advice to Kimbo was to keep the tempo slow at first until they were able to see how dangerous Petruzelli was. Kimbo refused to touch gloves before the fight with Petruzelli in his typical unsportsmanlike manner, and the proceeded to completely ignore Rutten's advice and charge in like a bull. Petruzelli defeated Kimbo via technical knock-out 14 seconds into the first round.
This fight spelled immediate controversy, as suspicions of foul play came to rise soon afterward. Many die hard Kimbo fans ironically claim that Kimbo was paid to throw the fight, which largely destroyed his MMA career and the promotion he was signed with. Excuses for the loss also came in the form of Petruzelli getting lucky, and blaming the referee for an early stoppage. Petruzelli also reported in an interview that EliteXC officials had hinted that he should keep the fight standing, instead of going to the mat, where Kimbo was by far the weakest.
In a win-win situation for UFC President Dana White, White signed Kimbo to be a contestant on the tenth season of the Ultimate Fighter reality TV show. If Kimbo loses on the show, Dana White will just say that he knew Kimbo would lose all along. If Kimbo wins, White will exploit his ridiculous star power to pull millions of fans (and dollars) to the UFC. White has been one of Kimbo's biggest critics, claiming that he is a joke and ruins MMA's image.
Even if Kimbo is able to prove these critics wrong and show that he can compete at the top of MMA, his career will most likely be short lived, as he is already 35 years old. More likely, The Ultimate Fighter Season 10 will be Kimbo's last attempt to resurrect the unprecedented hype that surrounded him in 2007 before he hangs his gloves up for good.
Real MMA Fan: "Are you serious? Kimbo is terrible. It was just a matter of time."
Kimbo Fan: "No he's not he's the best MMA fighter ever!"
Real MMA Fan: "I might agree if every other MMA fighter on the planet were to die of a sudden death."