When you talk about the most divisive gimmicks in all of wrestling, you wouldn't be surprised to see someone like "The King of Dong Style" Joey Ryan on the list. Some people love his work, others he just rubs the wrong way. But in AEW, it's "Freshly Squeezed" Orange Cassidy, who really brings out the smart marks. For every person that hates the guy, he' completely over with 20. The problem for AEW is how to book him as a wrestler without losing what he's successfully built as a character.
Cassidy first appeared with Chikara in 2004 as a masked wrestler called Fire Ant on a team of ant-themed wrestlers called The Colony. He would continue to work as Fire Ant in Chikara until 2018. Soon after, he would permanently switch to Orange Cassidy, a gimmick he had also used since 2009. "The King of Sloth Style" would debut in AEW in 2019, being referred to by some these days at the most popular wrestler in AEW.
What makesCassidy'ss gimmick unique is how little he actually seems to care about wrestling or anything else for that matter. His ring attire is usually well-worn jeans and a pair of aviators, which he often keeps on throughout the match. Cassidy frequently competes with his hands in his pockets, dodging attacks more than delivering them. The man's weight is generally billed as "whatever," and his place of origin is "wherever."
Love him or hate him, OrangeCassidy'ss gimmick is one of the most well thought out and executed in all of professional wrestling. When he accompanies Best Friends to the ring, he slowly wanders out, delivering lackadaisical thumbs up and fist bumps to a ravenous audience. Well, when there is one. The character profile on this gimmick is so thorough that Cassidy even has favorite movies, specifically the Fast and Furious franchise. They reputedly inspire him.
Cassidy rarely wrestles, primarily acting as a manager for the tag team Best Friends. But when he does get in the ring, he proves himself to be one of the most athletic and talented people out there. This was clearly evidenced at AEW Revolution when he took on Pac in an absolutely brilliant match. More recently on Dynamite, Rey Fenix and Orange Cassidy went one-on-one in a classic bout, which you would expect from two performers of that caliber.
Regardless of your personal feelings about the gimmick, Orange Cassidy is an incredibly impressive wrestler. The problem is that fact is a raging contradiction to his character. This leaves AEW in a bit of a bind from a booking standpoint, specifically how to maintain the popularity of one of its breakout stars while still putting on great matches. AEWdoesn'tt want to waste a talented in-ring performer who can put on main event worthy matches. At the same time, Orange Cassidy is reportedly one of their top merch sellers, due to fan connection with his gimmick. Every time he shows even the most minute amount of effort in the ring, it eats away at his slacker persona. For someone like Cassidy, trying just isn't cool.
One possibility would be to relegate Cassidy to purely a manager role, only having him get in spots during Best Friends matches when necessary. He has only had a handful of matches since joining AEW, so they're already part of the way down this path. The problem with that is Cassidy is so good in the ring that no one wants him to stop wrestling. As great as his gimmick is, his wrestling is what brought him to the dance.
Another idea, though not a particularly good one, would be to phase out the Orange Cassidy gimmick slowly. That's highly unlikely as he is so over with the fans that it's scary. Plus, AEW would never want to give up those merch sales, nor should they. AEW is a business and they need to make money. It's also unlikely that Cassidy would want to walk away from the gimmick. He spent a decade working on getting it over, and he's now seeing the fruits of his labors.
Fortunately, AEW has a prime example of how to handle this in R-Truth. In the business since 1997, Truth has found some of his greatest successes as a comedy act, a role he leans into and plays perfectly. Without his work, the 24/7 Championship would have been nothing worth paying attention to, a fact proven since he was largely removed from that scene. But his career has been filled with funny moments that fans loved, as well as fantastic matches.
WWE is notorious for micromanaging wrestlers, gimmicks and storylines, but they seem to trust R-Truth to be R-Truth. His instincts for effectively standing on the line between comedy act and talented wrestler are undeniable. Finding similar long-term success with Orange Cassidy means trusting him to manage his gimmick, both outside of the ring and in it. Overthinking and over managing comedy in wrestling just doesn't work, like singing karaoke with The Viking Raiders.
With Orange Cassidy, all you have to do is go back to those previously mentioned matches to see how he incorporates Sloth Style into the action. If you've never seen a lazy move off the top rope, you are in for a treat. Cassidy has also found ways to turn defense into an art form, showing off his speed while dodging attacks.
The secret is not limiting the amount Orange Cassidy wrestles, but increasing it. Get fans used to seeing Sloth Style in action and continue to develop it. By trusting Cassidy, AEW can protect a money-making gimmick and build his in-ring reputation, maybe even putting a championship he barely cares about on him. In the end, Orange Cassidy is one of the most popular gimmicks in AEW, if not all of wrestling. That's not going away any time soon.