Over the course of season six, several new wrestlers would emerge. One such notable performer was Create-A-Wrestler. A completely blank slate (similar to in video games making a new, original player character), this Wrestle Factory graduate allowed fans to decide his identity based on a series of contests. His identity for most of 2007 was Moscow the Communist Bovine. The next year he was mostly Ultimo Breakfast and the year after that he was Dasher Hatfield, a turn-of-the-century masked baseball player which he has remained to this day. 2007 also brought the popular stable the Osirian Portal featuring Factory graduates Ophidian and Amasis, an anthropomorphic snake and break dancing pharaoh. They perform what has been called the most illegal move in the history of wrestling as Amasis holds up Ophidian who hypnotizes their opponent(s). Likely the most well known use of the technique was in CZW where it hypnotized their opponents and the entire locker room into dancing (one wrestler even stripping). Also during the year, Chikara began developing a working relationship with Kaiju Big Battel, a Boston-based wrestling promotion that pays homage to many of the same things Chikara does as well. KBB features giant monsters and heroes (akin to Godzilla, Ultraman, etc) who air their battles destroying city blocks in the process for the amusement of the audience (their ring made to look like a city block complete with breakable buildings and props). At 2007’s Aniversario!, Dr. Cube (KBB’s primary villain) and Call-Me-Kevin battled Giii The Space Pirate and Dusto Bunny. Chris Hero appeared at several KBB events and, in 2008, KBB’s announcer Louden Noxious also became the announcer for Chikara as Gavin Loudspeaker (splitting his time between both promotions) as KBB performers found their way to perform at Chikara.
The next season of Chikara saw the seeds from the previous year begin to sprout. In order to uncover how Chris Hero learned to break the Chikara Special, Wrestle Factory graduate and Tecnico Tim Donst (who premiered the previous year) infiltrated the Order of the Neo-Solar Temple claiming he suffered amnesia at the hands of UltraMantis Black (in a podcast, Black alluded to knowing how Hero learned the break). Becoming the Chosen One, Donst teamed with Hydra and bided his time for two months until he uncovered the details. Donst learned Shane Storm revealed the secret to Black so the villain could use his magic to overturn Storm’s losing streak (the previous year, Black appeared and used his magic on Storm resulting in a victory). Donst immediately brought the news to Quackenbush, who was aware of his infiltration, just as Storm and Quackenbush earned their third victory necessary to challenge for the Campeonatos de Parejas (Jigsaw had moved on to ROH opening up Storm for another partner). Quackenbush was disgusted with his partner, ending their team (their right to challenge for the belts still intact to this day) and challenging his pupil to a match. Storm didn’t understand why his betrayal was so devastating and when he met his mentor in battle, Quackenbush went at him with a fury arguably never seen from him before. The teacher would defeat the student but when Quackenbush refused to break the Chikara Special he applied to win, the decision was reversed. Donst would convince Hydra to turn good and the two continued as a tag team.
While Chikara dealt with the discovery of Shane Storm’s betrayal, Vin Gerard returned with a vengeance. When his secret was revealed, the luchadores threw Gerard out and he came back to make them pay. The Rudo targeted anyone wearing a mask, affixing most of his attention on the Colony (who was becoming one of the most dominant stables in the promotion). This culminated into a battle with Fire Ant for the Young Lions Cup and while Gerard lost, he would later gain a rematch and win the trophy. Following the YLC tournament, Gerard convinced wrestler Jimmy Olsen his tag team partner and brother Colin (who had signed a deal with WWE) was hiding from him as a masked wrestler. Jimmy led a crusade to rip off the mask of every wrestler he could find (considered a disqualification in a match). Following Shane Storm’s battle with Quackenbush (where the Tecnicos turned their back on Storm following it), Gerard had Storm channel his anger and the Tecnico transformed into the monstrous Rudo Stigma. Soon after, Colin Delaney returned from WWE (using his name from that promotion) and joined Gerard and Stigma to form the UnStable while Jimmy Olsen realized he was played for a fool. Olsen dedicated himself to revenge, Gerard his primary target. After a time, Olsen adopted the identity of Equinox to get under Gerard’s skin, the season ending in a no contest battle between the two wrestlers. The season’s final battle saw Jigsaw return and join Mike Quackenbush to defeat Stigma and Delaney.
The eighth season would open up with Chikara’s first ladder match as Vin Gerard and Jimmy Olsen/Equinox went to war over Gerard’s Young Lions Cup with Equinox claiming victory. Appearing once toward the end of last season, Hallowicked would gain an apprentice in Frightmare who joined Incoherence. With Jigsaw back, Tim Donst saw his mentor Mike Quackenbush drift away from him toward the masked wrestler (though, Quackenbush would teach Donst the inverted Chikara Special out of gratitude) while Donst began to feel as though he was being dragged down by Hydra who he began considering to be a joke. The previous season, Claudio Castagnoli had an ongoing feud with wrestler Brodie Lee (Luke Harper in WWE) brought to a close in Chikara’s first cage match leaving Castagnoli to set his sights on the promotion’s other big man Eddie Kingston following their meeting in King of Trios ’09 (where Castagnoli teamed with one of his teachers Dave Taylor and “Best in the World” Bryan Danielson, known as Daniel Bryan in WWE). Kingston would go on to say Castagnoli isn’t the nice guy everyone thinks him to have become.