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#4. Tim Sylvia – UFC heavyweight champion
Tim Sylvia’s reign as UFC heavyweight champion could hardly have begun in worse fashion. After he captured the title from Ricco Rodriguez in 2003 and defeated Gan McGee in his first defense, he tested positive for anabolic steroids and was suspended by the Nevada State Athletic Commission, resulting in him being stripped of his title.
That didn’t put him fully on the outs with the UFC, though, who were willing to forgive and forget and immediately gave ‘The Maine-iac’ a shot at the vacant title upon his return. At that stage, Sylvia felt every bit the company man.
However, when he recaptured the title from Andrei Arlovski in 2006, his relationship with the UFC swiftly went downhill. He won the title with an exciting knockout, but his first two title defenses, against Arlovski in a rematch and then against Jeff Monson, were dull fights that angered UFC fans.
Dana White was clearly relieved when Randy Couture defeated Sylvia for the title in early 2007, and the relationship between the two didn’t get any better when Sylvia asked to fight Brock Lesnar when the former WWE star arrived in the UFC in 2008. Sylvia’s request was turned down, and when he then demanded his release from the UFC, he was quickly granted it.
‘The Maine-iac’ went onto fight for the short-lived Affliction promotion, but unlike others who fought under that banner, he was never brought back to the octagon afterwards.
According to Sylvia himself, the reason for that was because White held a grudge against him.
#3. Tyron Woodley – UFC welterweight champion
When Tyron Woodley won the UFC welterweight title in 2016 by knocking out Robbie Lawler, it felt like ‘The Chosen One’ would go on to become a superstar. But despite putting together four successful title defenses, he never quite reached the heights that many felt he would.
One reason for this may well have been his fractious relationship with Dana White. Woodley often accused the UFC of treating him unfairly when it came to the way he was promoted, which seemed to baffle White, who went onto label him the most difficult fighter he’d ever worked with.
White also claimed that he didn’t actually dislike Woodley, but at times it was hard not to come to that conclusion. After all, the UFC president was visibly frustrated with Woodley’s title defenses against Stephen Thompson and Demian Maia.
In fact, the UFC president outright slammed ‘The Chosen One’ after the fight with Maia, stating that nobody would want to pay to see him fight after his efforts and that there was no way he’d book him in a fight with Georges St-Pierre.
More recently, White has slammed Woodley’s upcoming fight with YouTuber Jake Paul, labeling the clash a “bunch of bullsh*t” and declaring Woodley’s claims that he’ll be making more money from the fight than he did in the UFC a lie.
