Moore initially trained alongside BlackJack Marciano and Jigsaw under Kevin Knight at the Independent Wrestling Federation in Woodland Park, New Jersey (formerly West Paterson).
After Moore was kicked out of the school, he became part of the second class of students to train at the Chikara Wrestle Factory, where he was taught by Mike Quackenbush and Chris Hero.

Moore made his professional wrestling debut, under the ring name Eddie Kingston, on October 12, 2002, at Chikara's seventh event, where he and BlackJack Marciano, the team known collectively as the Wild Cards, defeated Melvin Snodgrass and Lester Crabtree in a tag team match.
In 2003 Kingston and Marciano began feuding with Mister ZERO and UltraMantis, the team known collectively as Ultra/ZERO.
The feud came to an end on July 5, when Ultra/ZERO defeated the Wild Cards in the semifinals of the 2003 Tag World Grand Prix, after which Kingston and Marciano moved on to feuding with Team F.I.S.T. (Icarus and Gran Akuma).
The following year the Wildcards teamed up with Jigsaw to form the Toxic Trio, while Icarus and Akuma recruited the help of Mike Quackenbush.
On May 22, 2004, the Toxic Trio faced Icarus, Akuma and Quackenbush in an Ultimate Jeopardy match, where Kingston's, Marciano's and Icarus' hair, Jigsaw's and Akuma's masks and Quackenbush's various championship belts were on the line.
In the match Akuma forced Kingston to tap out and, as per stipulation of the match, both the Wild Cards were shaved bald, effectively ending the feud.
On September 18, 2004, the Wild Cards won the IWA Mid-South Tag Team Championship and enjoyed reasonable success outside of Chikara, until a knee injury forced Marciano into retirement, thus disbanding the team.

After taking a break from wrestling, Kingston returned to the ring in July 2005, turning fan favorite (face) and teaming with Sabian, Equinox and Quackenbush to take on The Kings of Wrestling (Chris Hero, Claudio Castagnoli, Gran Akuma and Arik Cannon).
On August 13, Hero defeated Kingston in a singles match, that would lead the two into feuding with each other over at Combat Zone Wrestling, while in Chikara they were kept apart from each other following the match.
For a majority of 2006, Kingston had a rivalry against Larry Sweeney.
Kingston and Sweeney traded many verbal and physical exchanges for months, and the feud culminated with a No Disqualification Strap match between the two at Chikara's last show of the year.
Kingston won this match and the overall feud.

In 2007, Kingston turned heel (villainous) when he was pinned in an eight-man tag team match.
Following the loss, Kingston attacked Hallowicked and attempted to remove his mask.
The resulting feud lasted for over six months.
During this time Kingston frequently forced his opponents to wear a replica of Hallowicked's mask.
The feud ended when Kingston defeated Hallowicked in a Falls Count Anywhere match.

Kingston, along with fellow BLKOUT stable members Joker and Ruckus, went on to the finals of the 2008 King of Trios tournament, coming up short against the team of El Pantera, Incognito and Lince Dorado, when Kingston tapped out to Dorado's Chikara Special.
After the tournament Kingston was not seen in Chikara for two months, but when he returned in May, he quickly targeted the man who had forced him to tap out at King of Trios, Lince Dorado.
Kingston defeated Dorado in back-to-back singles matches on July 13 and August 10, but both times Dorado refused to stay down and begged for more.
On September 7 Kingston and Dorado face each other in their third singles match, which ended when referee Bryce Remsburg disqualified Kingston due to "excessive punishment".
However, once again Dorado refused to stay down and demanded the match to be restarted.
After the restart, Kingston had himself disqualified by low blowing Dorado and then walked out, before declaring that he was done with Dorado, since he was making him mentally unstable with his actions.

In late 2008 Kingston would team up with Brodie Lee and Grizzly Redwood to form an alliance that would later be named The Roug
Moore initially trained alongside BlackJack Marciano and Jigsaw under Kevin Knight at the Independent Wrestling Federation in Woodland Park, New Jersey (formerly West Paterson). After Moore was kicked out of the school, he became part of the second class of students to train at the Chikara Wrestle Factory, where he was taught by Mike Quackenbush and Chris Hero.
Moore made his professional wrestling debut, under the ring name Eddie Kingston, on October 12, 2002, at Chikara's seventh event, where he and BlackJack Marciano, the team known collectively as the Wild Cards, defeated Melvin Snodgrass and Lester Crabtree in a tag team match. In 2003 Kingston and Marciano began feuding with Mister ZERO and UltraMantis, the team known collectively as Ultra/ZERO. The feud came to an end on July 5, when Ultra/ZERO defeated the Wild Cards in the semifinals of the 2003 Tag World Grand Prix, after which Kingston and Marciano moved on to feuding with Team F.I.S.T. (Icarus and Gran Akuma). The following year the Wildcards teamed up with Jigsaw to form the Toxic Trio, while Icarus and Akuma recruited the help of Mike Quackenbush. On May 22, 2004, the Toxic Trio faced Icarus, Akuma and Quackenbush in an Ultimate Jeopardy match, where Kingston's, Marciano's and Icarus' hair, Jigsaw's and Akuma's masks and Quackenbush's various championship belts were on the line. In the match Akuma forced Kingston to tap out and, as per stipulation of the match, both the Wild Cards were shaved bald, effectively ending the feud. On September 18, 2004, the Wild Cards won the IWA Mid-South Tag Team Championship and enjoyed reasonable success outside of Chikara, until a knee injury forced Marciano into retirement, thus disbanding the team.
After taking a break from wrestling, Kingston returned to the ring in July 2005, turning fan favorite (face) and teaming with Sabian, Equinox and Quackenbush to take on The Kings of Wrestling (Chris Hero, Claudio Castagnoli, Gran Akuma and Arik Cannon). On August 13, Hero defeated Kingston in a singles match, that would lead the two into feuding with each other over at Combat Zone Wrestling, while in Chikara they were kept apart from each other following the match. For a majority of 2006, Kingston had a rivalry against Larry Sweeney. Kingston and Sweeney traded many verbal and physical exchanges for months, and the feud culminated with a No Disqualification Strap match between the two at Chikara's last show of the year. Kingston won this match and the overall feud.
In 2007, Kingston turned heel (villainous) when he was pinned in an eight-man tag team match. Following the loss, Kingston attacked Hallowicked and attempted to remove his mask. The resulting feud lasted for over six months. During this time Kingston frequently forced his opponents to wear a replica of Hallowicked's mask. The feud ended when Kingston defeated Hallowicked in a Falls Count Anywhere match.
Kingston, along with fellow BLKOUT stable members Joker and Ruckus, went on to the finals of the 2008 King of Trios tournament, coming up short against the team of El Pantera, Incognito and Lince Dorado, when Kingston tapped out to Dorado's Chikara Special. After the tournament Kingston was not seen in Chikara for two months, but when he returned in May, he quickly targeted the man who had forced him to tap out at King of Trios, Lince Dorado. Kingston defeated Dorado in back-to-back singles matches on July 13 and August 10, but both times Dorado refused to stay down and begged for more. On September 7 Kingston and Dorado face each other in their third singles match, which ended when referee Bryce Remsburg disqualified Kingston due to "excessive punishment". However, once again Dorado refused to stay down and demanded the match to be restarted. After the restart, Kingston had himself disqualified by low blowing Dorado and then walked out, before declaring that he was done with Dorado, since he was making him mentally unstable with his actions.
In late 2008 Kingston would team up with Brodie Lee and Grizzly Redwood to form an alliance that would later be named The Roug
Eddie Kingston