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#4. James Toney
James Toney was one of the most technical and defensively sound boxers in history. A former multi-division champion, Toney possessed legitimate combat sports experience. Today, it is not unheard of for boxers to make the transition into MMA, as the likes of Holly Holm and Claressa Shields both have.
However, both women trained extensively to prepare for their bouts. Back in 2010, Toney expressed no such respect for mixed martial arts.
After signing a multi-fight deal with the UFC, Toney — who was scheduled to face the legendary Randy Couture — insisted that he'd knock his foe out cold, whether the fight was standing or on the ground.
By the time both crossed paths inside the octagon, Couture needed no more than three minutes to drag Toney to the ground and submit him with an arm-triangle choke in what was widely criticized as a freakshow. Despite the multi-fight deal he had signed, Toney was cut soon after.
#3. CM Punk
Longtime professional wrestler CM Punk is a highly credentialed figure in the world of sports entertainment. He has held multiple titles in WWE, AEW, and ROH. What Punk enjoyed in pro-wrestling, however, was something he severely lacked in MMA.
With no background in martial arts or combat sports, Punk's aspirations to become a mixed martial artist in his mid-30s were more than unrealistic. News of his signing caused uproar in the MMA world.
Fighters made mention of how many hard-working mixed martial artists in other promotions deserved the opportunity over Punk, who had no prior fights or experience.
His friendship with Dana White and the UFC's desire to capitalize on Punk's relative popularity in pro-wrestling were cited as reasons behind the promotion's decision. In an organization intent on legitimitizing the sport of MMA, signing Punk was considered a step backwards by many.
Worse still, Punk's first bout was on the main card at UFC 203, right below the co-main event. His opponent was Mickey Gall, a 2-0 fighter who only needed two minutes to secure a takedown and defeat Punk with a rear-naked choke.
Punk's subsequent bout was his last as he lost a 3-round drubbing to Mike Jackson before Dana White implored the former WWE champion to reconsider his career decisions.
