Kingston joined Combat Zone Wrestling (CZW) and was almost immediately placed in the role of enforcer and mouthpiece in the BLKOUT faction. Kingston and fellow BLKOUT member Joker won the CZW World Tag Team Championship from the Kings of Wrestling (Chris Hero and Claudio Castagnoli) on February 11, 2006, at "Seven Years Strong: Settling The Score." Seven months later on September 9, Kingston defeated Chris Hero to win the CZW World Heavyweight Championship after an extended feud. As a result of winning the CZW World Championship, BLKOUT vacated the tag team championship, and the Kings of Wrestling won them in a tournament, but were attacked by BLKOUT afterwards. After a successful world title defence against Justice Pain at "Night of Infamy 5", due to Hero interfering and accidentally hitting Pain, Kingston lost the title to Pain in a three-way elimination match, also involving Hero. Kingston was eliminated first, after suffering a legitimate broken ankle, after botching a backdrop.