The video with Byrd spread to countless internet MMA forums, eventually making its way to the MMA.tv website, where Boston police officer and amateur MMA fighter Sean Gannon noticed it. As the legend goes, Gannon saw the video, thought little of Kimbo's skills, and challenged him.

Both fighters were fatigued to the point of collapsing, and Gannon's face was brutally mangled. Reportedly, the spread of the fight video prompted the UFC to invite Sean Gannon to UFC 43, and leading up to Gannon's match, commentator Joe Rogan mentioned several times Kimbo Slice, the video of the fight, and its internet attention.

As seen during the video, there was much controversy over the fight's rules, particularly when Sean Gannon attempted a guillotine choke. It's known that Kimbo only accepts stand-up fights. Gannon claims that Kimb's crew sayed no rules would be enforced but when Gannon came to the fight Kimbo's crew hastily made rules up. Gannon states that takedowns and submissions on the ground were not allowed but Kimbo's crew said nothing about knees and standing submissions.

It was rumored that a fight with Kimbo required a $10,000 bet from both sides. On the MMA.tv boards, Gannon hinted at this, saying, "Anyone who enjoyed the fight should kick him a little something. He earned it." A post from Kimbo's management, Southbeat Records, also mentioned a wager of ten thousand dollars, and added that a challenger need not have any fighting experience, only money to bet.