#1. He shouldn't: Daniel Bryan has been in WWE for a long time now

Daniel Bryan's relationship with WWE dates back to the early 2000s, but he only got his big break in 2010. Even then, he was fired but quickly rehired. That kickstarted an incredible run for him, where he has won five World Championships and main evented WrestleMania twice.
With victories over the likes of Triple H, John Cena, Batista, Randy Orton, AJ Styles, and more, Daniel Bryan has had a Hall of Fame-worthy career in a decade that saw him emerge as the hottest star in WWE, have a tragic retirement, as well as a miraculous comeback two years later.
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An argument can be made that a decade is long enough in WWE and that Bryan has earned the right to go and explore other options. Those fans that want to see him wrestle non-WWE stars would make a case for how a decade is long enough with one promotion, and that Daniel Bryan has no obligation to retire in WWE.