#1 Kenny Omega vs. Orange Cassidy
Given the talents of these two men, they could comfortably put on a stellar comedy bout, similar to the one that took place between Orange Cassidy and PAC at the AEW Revolution PPV.
However, it would make sense for AEW to book a feud between a 'heel' Kenny Omega up against a 'babyface' Orange Cassidy. There has been criticism online amongst the AEW fanbase over the booking of Kenny Omega as many feel he has not been used to his full potential. However, his in-ring abilities are never in doubt as he is the best pure wrestler in the company right now.
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It seems like it is just a matter of time before AEW puts the World Title on Omega, and he becomes the front and center of the programming. Orange Cassidy has been awesome whenever he is on TV and is no slouch in the ring either. It would make for enthralling viewing if he were to challenge Omega for the title eventually.
AEW has done well to keep Cassidy's character a hot property, and he feels like a major star in the making. AEW would be well aware that there is lots of money to be made from Omega's run to the top. With Cassidy getting the opportunity to dethrone him, it would make for a jaw-dropping moment.