After leaving ROH in 2015, Ciampa went to a WWE tryout, and despite feeling like he impressed officials, he was told "no" by management. However, the door was open for Ciampa to join the company in the future. The future turned out to be a month later when Ciampa and Johnny Gargano were added to the Dusty Rhodes Tag Team Classic.
"The tryout was June, the 'no' was July, and Regal calls us in August to say 'there's a Dusty Classic coming up. [You and Gargano] are going to have a tag match. It might be nothing. Are you interested?' We were like, 'Yeah.' We did that first match and we got a shock win, the second one we came in to put over [Baron] Corbin and Rhyno. But the crowd helped us and our work ethic, appearance, how we handled ourselves," Ciampa told Lilian Garcia on Chasing Glory.
Ciampa wasn't signed until 2016, and even then he wasn't under an exclusive deal. However, he started to form a bond with Triple H during his time under contract, leading to Ciampa pitching himself to be in the Cruiserweight Classic to face Johnny Gargano in the first round.
"Hunter has become [a mentor], but not even just in wrestling," said Ciampa. "In life, in a sense. When Johnny and I got the opportunity, we did a couple of matches and were doing the tag thing. But we could tell they didn't have a vision for us. We weren't the two dudes debuting at TakeOver and having the big entrance. We were like, 'How do we get over to the point where they see in us that they should sign us and use us.' Hunter was accessible. It wasn't intimidating seeing him and trying to build that relationship. The Cruiserweight Classic came about and I wasn't going to be in it, but Johnny was. That's when I had my first talk with Hunter and I said, 'What if you put me in the Cruiserweight Classic and that first round, it's a lot of throwaway matches, but you put me vs. Johnny and I'll put him over. At least you have a really good match in the first round.' That became my initial thing with Hunter where we hit a home run and instantly, you hit a home run for someone, you earn trust."
Ciampa went on to reveal the roadblocks that seemed to prevent him from signing a full-time WWE deal. The first was WWE finding out about an old interview he did about depression, which worried WWE about his mental state. Ciampa stated he discussed the issue with Triple H, clearing up any concerns. It was later revealed by WWE medical that Ciampa had suffered a torn labrum. Instead of getting surgery and having to go through another tryout process since he wasn't on an exclusive deal, Ciampa once again went to Triple H.
"They send us to medical and find out I have a torn labrum in my shoulder," Ciampa recalled. "Normally, the way they handle it is get it fixed, comeback, and do a tryout. I went straight to Hunter and said, 'Did anyone speak to you? I feel fine. What do you want me to do? If you tell me to go get surgery, I'm not doing it. I'm gonna keep wrestling.' I was doing so well and now that I had NXT exposure, I'm doing really well. I didn't even know it was there. I'm training every day and have no symptoms. 'I'm not gonna fix it. If you tell me to fix and come back in six months, we're done here in the most amicable way possible.' He's like, 'How terrible of a person am I if I've been using you for a year, this might have happened on our show.' We have a discussion and it ends up becoming, he says, 'Instead of this makeshift contract, if you're willing to come to Florida and have a full-time deal, then, when the time comes you tell us you have to take care of your shoulder, we'll take care of it. But, you gotta come to Florida.'"
Ciampa noted that he did eventually get surgery on his torn labrum, but only when he had to go in for ACL surgery. He also noted that Gargano was offered a deal at the same time, and he was upset about leaving Cleveland.
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