4. Tyron Woodley
I've always considered Woodley a fascinating champion, so much so that I've written an article about him. Essentially, Woodley employed a fighting archetype that had attained great prominence and success in the late 2000s but long since became antiquated at the elite levels, yet Woodley used it to lord over one of the best divisions in the sport as late as 2019. This was the same archetype, a dominant wrestler with a powerful cross, as fellow list member Johnny Hendricks, only Woodley was more successful with it, and for longer. Before 2019, Woodley had some spectacular wins over fighters including Carlos Condit, Josh Koscheck, Tarec Saffiedine, Paul Daley, Jay Hieron, Dong Hyun Kim, Demian Maia (even if it was boring!), Darren Till, and then a tremendous pasting of Robbie Lawler to win the crown. He also took some bad losses, like being knocked out by Nate Marquardt and dominated by Rory MacDonald, and Woodley benefited from judging in several close fights that could easily have been decided differently, such as his majority draw against Stephen Thompson, his majority win in their rematch, or his split decision win over Kelvin Gastelum, though he did have a split decision loss to Jake Shields.
Woodley's historical placing suffered greatly near the end, as he went on a four-fight losing streak to end his career, with Kamaru Usman, Gilbert Burns, Colby Covington and even Vicente Luque taking turns administering one-sided beatings to the former champ. While Usman and Covington likely would have beaten even a prime Woodley, this was exacerbated by how much Woodley's style was predicated on quick reactions and instincts, which naturally slowed as he aged. Still, this shouldn't obscure how great Woodley was in his prime or that he was champion until he was almost 37, and that deserves a high place on this list.
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