Starting with his win over Equinox (Vin Gerard) at "CHIKARA Aniversario?" on May 26, 2007, went undefeated in singles competition in CHIKARA for a year until Claudio Castagnoli defeated him by disqualification at "CHIKARA AniversarioCT" on May 24, 2008.
UltraMantis Black defeated him in a Block B match of the CHIKARA 12 Large: Summit round-robin tournament to crown the inaugural CHIKARA Grand Champion at "CHIKARA Aniversario: The Legendary Super Powers Show" on May 22, 2011. He suffered an injury that took him out of the rest of the tournament.
Teamed in CHIKARA with Eddie Kingston (Edward Moore) and Grizzly Redwood (Matt Krizovensky) as the Roughnecks. He was part of the Miracle Ultraviolence Connection with Cheech Hernandez and Cloudy (Eric Downes), the Hillbilly Wrecking Crew with Necro Butcher (Dylan Keith Summers) and Trevor Murdoch (William Mueller), and the stables WARRIORS in Dragon Gate, Blood WARRIORS in Dragon Gate and Dragon Gate USA, WARRIORS International in Dragon Gate USA, and the Age of the Fall in Ring of Honor.
At "CHIKARA Style and Substance" on September 7, 2008, faced Claudio Castagnoli in the first-ever steel cage match in CHIKARA history, which Claudio won.
After switching to the trucker gimmick, he used Johnny Cash's "God's Gonna Cut You Down" as entrance music.
Brodie Lee was billed from "The Open Road.".