Speaking with ESPN, Cassidy reflected on how Matt and Nick Jackson were determined to sign him. The brothers eventually got their wish granted when Cassidy officially debuted for AEW at 2019’s All Out pay-per-view. He had previously participated at Double or Nothing’s Casino Battle Royale.
“The Young Bucks were the people that were like, ‘We need to get Orange here,'” Orange Cassidy said. “Because my character is a giant middle finger to professional wrestling, so they were like, ‘Of course, let’s get him in.'”
Cassidy aligned himself with Best Friends, Chuck Taylor and Trent Beretta. The trio have been teaming with and accompanying one another ever since.
Recognizing Cassidy had a following, Khan explained how “[…] he wasn’t somebody, when we started, that I was really particularly aware of or had real big plans for,” Khan said. “[After Double or Nothing,] I spent a lot of time with Orange Cassidy and got to know him a lot better, and also talked to him about ideas, and that opened a lot of doors for both of us.”