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#3 James Toney
A former three-weight champion in boxing, James Toney was one of the most accomplished fighters of the 90s and early 2000s, having held the IBF Middleweight Title, the IBF Super-Middleweight Title, and the IBF Cruiserweight Title during a decorated career. He was even voted Fighter of the Year twice by the prestigious Ring Magazine – an even bigger feat given the first time was in 1991 and the second over a decade later in 2003.
It was unfortunate that Toney’s MMA debut came in 2010 – five years after he’d won the WBA Heavyweight Title, only to have the belt stripped due to a positive test for anabolic steroids. By 2010, Toney was a bloated shell of his former self but was still signed by Dana White after talking huge amounts of trash on the UFC and MMA in general. He claimed he didn’t need any more skills than his boxing to get past the UFC’s top fighters.
Matched with Randy Couture at UFC 118, Toney quickly discovered that his boxing skill was practically useless inside the cage with a fully rounded mixed martial artist. The legendary Couture used a simple ankle pick to put Toney on his back and from there the fight was basically over. Randy advanced to full mount before slapping on an arm triangle choke and Toney couldn’t even manage to tap out correctly, waving his hand wildly instead.
Naturally, he never fought in MMA again, but thankfully his trash-talking mouth had been shut for good thanks to Couture – perhaps the last time the former champion was in Dana White’s good books.
