[8] Hallowicked made his professional wrestling debut on Chikara's inaugural show on May 22, 2002, as a member of the three man rudo (bad guy) stable Night Shift, with partners Blind Rage and Ichabod Slayne.

[9] On the second show on May 31 Night Shift picked up their first victory in a six-man tag team match against Don Montoya and their trainers Mike Quackenbush and Reckless Youth.

[15] Night Shift's success was not limited only to Chikara, as during this time they were also able to win North American Wrestling Federation's Tag Team Championship.

In October 2004 the Dark Breed joined Larry Sweeney's stable Sweet 'n' Sour International for the first annual torneo cibernetico match.

[22] Hallowicked's apparent tecnico (good guy) turn did not sit well with UltraMantis Black as after the tournament he announced the death of the Dark Breed and declared a war on his former partner.

[5] During the course of the feud Hallowicked and Delirious managed to pick up the three points needed in order to challenge for the Campeonatos de Parejas on and October 26, 2007, they defeated Icarus and Chuck Taylor, who replaced the injured Gran Akuma in the title match, to end their record setting reign and become the new Champions.

[26] However, Hallowicked's year would end on a low note, as on November 18 Kingston defeated him in a Falls Count Anywhere match to win their feud.

The first match of the feud on February 28 ended when BDK members Sara Del Rey and Daizee Haze were disqualified for excessive punishment on Frightmare, giving Incoherence their first point in the process.

(Icarus and Gran Akuma), then the Order of the Neo-Solar Temple (UltraMantis Black and Crossbones) and finally Sara Del Rey and Daizee Haze of BDK to earn their second, third and fourth point respectively.

[36] At Aniversario Elf Incoherence was defeated in their title match in two straight falls, thanks to a pre-match assault from BDK's newest member Delirious and some shady officiating from the stable's own referee, Derek Sabato.

After the match UltraMantis was attacked by Sinn Bodhi and his allies in The Batiri, but were eventually chased out of the ring by Incoherence, after Frightmare managed to convince Hallowicked to save his long–time rival.

[39] On April 15, 2011, Hallowicked, Frightmare and UltraMantis Black, now known collectively as the Spectral Envoy, were eliminated from the 2011 King of Trios in the first round by Team Dragon Gate (Akira Tozawa, KAGETORA and Super Shisa).

[40][41] The Spectral Envoy and the Dark Army (Sinn Bodhi, Kobald, Kodama and Obariyon) faced each other in an eight-man tag team match on September 18, when the former was joined by UltraMantis Black's former Order of the Neo-Solar Temple partner Crossbones.

[40] On November 13 at Chikara's first internet pay-per-view, High Noon, Hallowicked and UltraMantis Black put their masks on the line against Ares' Eye of Tyr and Donst's hair in a No Disqualification match.

The match ended with UltraMantis pinning Ares, which meant that not only did he win back the Eye of Tyr, but he and Hallowicked also earned their third point and the right to challenge for the Campeonatos de Parejas.

[44] On September 14, Hallowicked, Frightmare and UltraMantis Black entered the 2012 King of Trios, defeating Mihara, The Mysterious and Handsome Stranger and Tito Santana in their first round match.

[40][51][52] On December 2 at Chikara's third internet pay-per-view, Under the Hood, the Spectral Envoy, represented by Frightmare, Hallowicked, UltraMantis Black and the returning Blind Rage and Crossbones, defeated The Batiri, Delirious and Ophidian in a ten-man tag team match.

They were, however, eliminated in their first round match by Eddie Kingston, Jimmy Jacobs and Volgar, representing Chikara's new top rudo stable The Flood, after their stablemate Deucalion brought out Delirious to attack UltraMantis.

[56] On December 6 at Tomorrow Never Dies, Delirious used the supposedly magical artifact Eye of Tyr to brainwash Hallowicked and Frightmare into turning against UltraMantis Black, breaking up the Spectral Envoy.

[63] In September, Hallowicked, Frightmare and Silver Ant represented the Nightmare Warriors in the 2015 King of Trios, where they made it to the quarterfinals, before losing to eventual tournament winners, Team AAA (Aero Star, Drago and Fénix).

[65] On January 30, 2016, at the season 16 premiere, Hallowicked and Frightmare unsuccessfully challenged N_R_G (Hype Rockwell and Race Jaxon) for the Campeonatos de Parejas.

After Hallowicked used the Eye of Tyr to turn UltraMantis Black to his and Frightmare's side,[68] the group expanded to also include Icarus, Kobald, Kodama, Mark Angelosetti and Obariyon.

[70] The following day, Hallowicked, Icarus and Jigsaw defeated Major League Moustache (Dasher Hatfield, Trent Seven and Tyler Bate) to advance to the semifinals of the tournament.

[71] On the third and final day of the tournament, Hallowicked, Icarus and Jigsaw were eliminated after being disqualified in their semifinal match against Team JWP (Command Bolshoi, Hanako Nakamori and Manami Katsu).

[74] On December 15, 2006, Hallowicked made his debut for Florida-based Full Impact Pro (FIP) in a tag team match, where he and Gran Akuma defeated DP Associates (Delirious and Shingo).

[2] On April 27, 2007, Hallowicked, along with fellow Chikara wrestlers Mike Quackenbush, Jigsaw and Gran Akuma, made their debuts for FIP's sister promotion Ring of Honor (ROH).