#4. Tim Sylvia – former UFC heavyweight champion
When he departed the UFC in 2008, Tim Sylvia was still widely recognized as one of the world’s best heavyweights.
Sure, he left the octagon following a loss to Antonio Rodrigo Nogueira, but there was no shame in that. In the same way, there was no shame in his subsequent loss to Fedor Emelianenko under the Affliction banner months later. However, it didn’t take long for the former UFC heavyweight champion to suffer a truly embarrassing loss, one that his MMA career never really recovered from.
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For reasons known only to him, ‘The Maine-iac’ decided to accept a bizarre fight with former WBO heavyweight boxing champion Ray Mercer at a regional show promoted by his own manager Monte Cox.
The fight was originally promoted as a boxing match, only for it to be switched to hybrid rules, and finally full MMA rules at the behest of Alabama’s boxing commission. And given that Mercer was pushing 50 at the time, few people figured he’d give Sylvia a lot of trouble.
Nobody gave ‘Merciless’ that memo, though, and just nine seconds into the fight, he slipped a sloppy jab and landed a crushing right hook to the jaw of Sylvia. The shot knocked the former UFC champion silly.
‘The Maine-iac’ fell to the ground in such an exaggerated fashion that it looked like Mercer had tackled him. Much to Sylvia's embarrassment, the fight was immediately called off.
Footage of the knockout instantly went viral. Essentially, Sylvia’s career as a top-level MMA fighter was over. Affliction MMA quickly dropped him and despite a number of wins on the regional circuit, he never did make it back to the UFC.
#3. Johny Hendricks – former UFC welterweight champion
When Johny Hendricks announced his retirement from MMA in 2017 following a loss to Paulo Costa at UFC 217, it felt like the right time for him to go.
The former UFC welterweight champion had been on a slide ever since losing his title to Robbie Lawler at UFC 181. Following that loss, he’d won just two of his next seven fights in the octagon.
More worryingly, Hendricks was stopped by strikes in three of those five losses, suggesting that his chin was thoroughly shot after a decade of high-level MMA competition.
Naturally then, UFC fans were concerned when they heard he’d be returning to action in 2018 in the form of a bare-knuckle boxing career. This path had already been trodden by a number of former UFC stars. It had rarely led to anything good.
Hendricks was signed to fight former Bellator tournament champion Brennan Ward in his bare-knuckle debut. However, it seemed like Lady Luck was on his side when Ward withdrew from the fight days before the event, citing a contract dispute.
The WBKFF promotion replaced Ward with Dakota Cochrane, a journeyman MMA fighter who had spent the majority of his career at lightweight and had never fought bare-knuckle before. Given that Cochrane, who also earned fame as a gay porn star, was largely known for his grappling, it seemed like a winnable fight for ‘Bigg Rigg’.
Unfortunately, that wasn’t the case. The smaller Cochrane managed to hurt Hendricks with a combination in the second round. Moments later, the former UFC champion wilted under the power of a flurry, going down to a TKO.
It was a horribly embarrassing loss, and only served as a reminder to Hendricks that his time in combat sports was almost certainly up.