Ahead of an All Elite Wrestling (AEW) show at Agganis Arena in Boston on Wednesday night, Boston 25 got a chance to sit down with one of their wrestlers: “Freshly Squeezed” Orange Cassidy.

In September 2018, a group of ambitious wrestlers promoted and held an independent wrestling show. It sold all 11,263 tickets in just 30 minutes. Soon after, a trademark was filed: All Elite Wrestling.

In May the following year, AEW launched its first official pay-per-view event. That’s when the world was introduced to Orange Cassidy.

Cassidy says there was no formal tryout, or even a phone call. Instead, his good friends and fellow wrestlers Trent Beretta and Chuck Taylor, a tag-team duo called “Best Friends,” helped him get his foot in the door.

“They said, ‘Hey, we have an extra spot. Do you want to do it?’ And I said, ‘Sure.’ And then it just took off from there.”

Later that year, AEW landed a television deal. Cassidy made his “AEW Dynamite” debut on its second episode, which incidentally was at Agganis Arena in Boston.

The laid-back, sunglasses and jean-jacket-wearing wrestler gives off a “whatever” appearance. The manner in which the ring announcers call him down to the ring backs it up.

“Making his way to the ring.. From.. wherever… Weighing.. whatever.. “Freshly Squeeeezed” Orange.. Cassidy!”

Before AEW, Cassidy had been bouncing around various independent promotions, or the “indies,” for nearly 15 years.

He said the origins of his cool, laid-back “whatever” character started organically.

“So then I just stopped caring, and that seemed to stand out, so I stopped caring even more,” Cassidy explained.

The positive with not caring, Cassidy said, is that he, in turn, didn’t care if the character was going to get over with fans. But it did.

“It was almost very freeing, I was like, ‘Well, I ain’t got nothing to lose. No one is looking at me, I don’t care. So, that was very liberating, and I got to do what I wanted,” Cassidy said.

Now a part of a legitimate company with multiple shows on major networks each week, Cassidy says he’s grateful that AEW lets him be creative, especially when it comes to cutting promos.

“Nobody tells me what to say. No one demands I say something. I get a lot of suggestions,” Cassidy said. “And we do have very smart, talented people backstage giving me suggestions that are far better than mine, but it’s never a script. And if there is a script, it’s more of an outline.”

He added, “It’s good that I have a boss and a company that says ‘go ahead, try it out.’”

Another reason Cassidy is grateful for AEW?

“Getting paid more than $20 per show is nice,” he said.

Cassidy recently turned in his first 5-star match. It’s an unofficial metric, but the rating system by wrestling journalist Dave Meltzer has been a staple in the wrestling community.

The match was last Wednesday, a grueling and bloody 5-vs-5 match in a cage.

When asked if Cassidy cares about that kind of stuff:

“I do not,” Cassidy said. “His ratings and opinions carry a lot of weight, but I just don’t care.”

In other words, whatever.

You can catch Orange Cassidy and the rest of the AEW roster on Wednesday at 7:30 p.m. at the Agganis Arena in Boston.

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