James Toney is different from the other fighters on this list in that he became famous thanks to his boxing career, where he who won belts in multiple weight classes.
However, by late 2009, Toney was in his 40’s at the tail-end of his career and struggling to find opponents in the boxing ring, and so he personally attended UFC events and eventually convinced Dana White to sign him.
What wasn’t public knowledged at the time was that Toney was in serious financial troubles and saw his blockbuster MMA vs. boxing fight in the Octagon with Randy Couture at UFC 118 in the summer of 2010 as his best chance to dig himself out of that hole.
Toney was understandably a heavy underdog going into the fight, and as many predicted Couture using his wrestling to take Toney down and hand him a first round submission loss.
Nevertheless, Toney had been all set to take home a bumper $500,000 salary for his night’s work…right up until IRS officials seized his entire fight purse the night before the bout due to unpaid taxes.