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3. Gerard Gordeau vs. Yuki Nakai
Vale Tudo Japan 1995
April 20, 1995 | Tokyo

Gordeau, if you recall, competed in the first-ever Ultimate Fighting Championship bout, soccer kicking Teila Tuli’s tooth into the front row at McNichols Arena in Denver. He also reached the UFC 1 tournament final, where he lost to Royce Gracie and earned a permanent place in the MMA history books.

Some two years later, Gordeau fought Nakai in the first round of the Vale Tudo Japan 1995 tournament; and it got ugly. Nakai buried his face in Gordeau’s chest, as the two men clinched along the ropes. Not much appeared to be happening. After some time, the Dutchman jammed his left thumb into Nakai’s right eye, leaving it badly damaged. Nakai fought on. The three referees, one inside the ring and two outside, witnessed the act and began visibly yelling at Gordeau. He simply shrugged and played innocent, as if to say, “Whatever do you mean?”

Nakai ultimately submitted Gordeau with a fourth-round heel hook and then defeated Craig Pittman in the semifinals before running into Rickson Gracie in the final. There, he bowed out via rear-naked choke. Nakai never fought again and became permanently blind in his right eye, thanks to Gordeau.

Number 2 » Breaking the Rules