Huber made his debut for Philadelphia-based Chikara on March 24, 2007, at Time Will Prove Everything, using the ring name "The Right Stuff" Brodie Lee and losing to Equinox. Lee would return to the company two months later, defeating Equinox in a rematch and starting a streak of not being pinned or submitted that would last for the rest of the year. In August Lee aligned himself with the Olsen Twins (Colin and Jimmy Olsen) and adopted the new nickname "Big Rig" and the gimmick of a trucker. Lee and the Olsen Twins were scheduled to enter the 2008 King of Trios tournament as Team Dr. Keith, but after Colin signed a contract with World Wrestling Entertainment (WWE), the team was left one man short. A random draw picked Retail Dragon as his replacement, but after he dropped the deciding fall in their opening round match against Cheech, Cloudy and m.c.KZ, Lee turned on him, also ending his alliance with Jimmy Olsen in the process.
In April 2008 Lee's bullying of smaller wrestlers, led to Claudio Castagnoli issuing a challenge to him. Their first match on April 20 ended in Castagnoli being disqualified for accidentally kicking the referee of the match. The second match on May 24 ended in similar fashion, this time Lee was disqualified for kicking the referee. This led to a No Disqualification match on July 13, which Lee won after interference from Shayne Hawke and Mitch Ryder, both of whom had a grudge with Castagnoli for breaking up the Kings of Wrestling the previous year. Lee's and Castagnoli's feud ended on September 7, 2008, in Chikara's first ever steel cage match, with Castagnoli coming out victorious.
In late 2008 Lee aligned himself with Eddie Kingston and Grizzly Redwood to form the stable The Roughnecks. On February 21, 2009, The Roughnecks defeated UltraMantis Black, Crossbones and Sami Callihan to earn a spot in the 2009 King of Trios tournament. On March 27 The Roughnecks lost their King of Trios opening round match to Team Uppercut (Bryan Danielson, Claudio Castagnoli and Dave Taylor). When Kingston moved on to feuding with Castagnoli, Lee and Redwood began wrestling matches as a tag team. With victories over Los Ice Creams (El Hijo del Ice Cream and Ice Cream, Jr.), Cheech Hernandez and K.C. Day and the North Star Express (Darin Corbin and Ryan Cruz), Lee and Redwood earned their right to challenge for the Campeonatos de Parejas. On October 17, 2009, Lee and Redwood challenged The Colony (Fire Ant and Soldier Ant) for the Championship, but were defeated in two straight falls. Lee opted to give Redwood one more chance, but when he dropped the fall on October 19 in a match against The Osirian Portal (Amasis and Ophidian), Lee kicked him in the face, effectively ending The Roughnecks. Redwood made his return six months later on April 24, 2010, as a surprise opponent of Lee's, but was easily defeated by him. Afterwards Redwood stated that he was not done with Lee, but would prepare himself before their next match. On August 29 Lee entered the Countdown Showdown battle royal and was dominating the match, before being eliminated by Redwood. On October 23 Lee suffered an upset loss in a match against Dasher Hatfield, who was defeated by Redwood the following day. On November 20 Lee and Redwood, having earned each other's respect, re–united and attacked Hatfield after his match with Shayne "Buck" Hawke. On January 23, 2011, at the season ten premiere, the Roughnecks defeated the Throwbacks (Hatfield and Sugar Dunkerton) in a tag team match. The Roughnecks and the Throwbacks ended their feud on March 13 in a lumberjack match, where Hatfield and Dunkerton were victorious. In May 2011, Lee entered the 12 Large: Summit, set to determine the inaugural Chikara Grand Champion, but was forced to pull out of the tournament following his first match, after suffering an injury. Lee returned to Chikara on October 30. After signing a developmental contract with WWE, Lee made his farewell appearance for Chikara on March 25, 2012, when he unsuccessfully challenged Eddie Kingston for the Chikara Grand Championship.