Woodley has had a difficult time since his reign as UFC welterweight champion from 2016 to early 2019. "The Chosen One" has now lost six consecutive fights, beginning with his title loss to Kamaru Usman at UFC 235 and most recently failed in back-to-back boxing contests against Jake Paul in 2021.

Woodley, 40, is presently a judge on the PFL's Challenger Series, determining which champions advance to the main season. Meanwhile, he continues to investigate the various choices available in the combat sports sector.

“I’m a free agent and I’m enjoying my liberation. I’m enjoying doing what I want to do,” Woodley told BJPenn.com. “Fighting when I want to fight and fighting for the amount of money I want. I’m the only guy in this sport that can do that.”

“I know some guys are just recently free agents but with the magnitude of what I’m doing right now, nobody is doing. To be the trailblazer and the one and only and be the first fighter that can go and box, kickbox, Muay Thai, I can do Bellator, ONE, PFL, or Glory. I can do my own s*** and make top dollar. I’m very thankful, very blessed.”

Dealing with PFL has also led to discussions of fighting for the former UFC champion. Woodley stated that he and PFL President Peter Murray would likely look into PPV event options before the Challenger Series ended. The promotion will begin its new PPV venture with two events outside of the usual season schedule in 2023.

After leaving the UFC on a four-fight losing streak and believing he was not treated fairly as champion, Woodley believes a return to the UFC is not out of the question.

“I have no door closed,” Woodley said. “I’m a businessman, I can fight in any business I want to. I can fight in any organization I want to. ONE, Bellator, Glory, PFL, UFC. I don’t get my feelings hurt in business.”