Lee made his debut for Syracuse, New York-based Squared Circle Wrestling (2CW) on August 20, 2007, teaming with Colin Olsen, as a replacement tag team partner for Jimmy Olsen, in a tag team match, where they were defeated by the Wyld Stallyns. Lee started off as a heel aligned with the rival promotion NWA Upstate. Lee started becoming popular after a July 26, 2008, post–match incident in Binghamton, New York that ended with him punching out a fan in the parking lot. Lee was in storyline suspended from 2CW over the incident. He returned on October 24 to a huge ovation, although he was still a heel, leading NWA Upstate to a victory in an eight-man tag team main event. He officially became a Babyface starting April 2009 when the rivalry between 2CW and NWA Upstate had subsided. Lee then started a friendly rivalry with Slyck Wagner Brown that saw both men trade wins in singles matches on June 6 and September 19, 2009. Lee defeated Brown in a rubber match on February 19, 2010, and then again in a two-out-of-three falls match on April 3, 2010, to end the feud. Lee challenged Jason Axe for the 2CW Heavyweight Championship on June 20, 2010, but lost due to outside interference. Lee defeated Isys Ephex on July 10 in a number one contender match to earn another shot at the title and, on August 22 in Watertown, New York, defeated Jason Axe to win the 2CW Heavyweight Championship for the first time. Lee made a successful first defense of the title against the former champion, Jason Axe, in an "I Quit" match in Binghamton, New York, on September 24, 2010. Lee lost the title to Slyck Wagner Brown on November 19, 2010, in Elmira, New York. Lee regained the title on April 13, 2012, in a four-way match with Jay Freddie, Slyck Wagner Brown and Kevin Steen, who stole the championship belt after the match. The following night, with the title belt still in Steen's possession, Lee successfully defended the 2CW Heavyweight Championship in another four-way match against Jason Axe, Jay Freddie and Matt Milan and afterwards relinquished it, as he had signed with WWE and would be contractually unable to defend it in the Future.