Kennedy's self-ring introductions before the match became one of his trademarks. did not interest him anymore because he had already defeated every top performer on the roster. General Manager Theodore Long making a match between Kennedy and The Undertaker, who Kennedy had never faced, to be held at No Mercy. However, Long put him against an opponent who he had never faced—this time Chris Benoit—with Kennedy's title on the line.
Long said that, if Kennedy were to defeat Benoit, he would be given his release and be allowed to go to Raw.
on January 5 and defeated Chris Benoit in a "Beat the Clock" match, with the overall prize being a shot at Batista's World Heavyweight Championship at the Royal Rumble.
On the August 20 episode of Raw, Carlito hosted the interview segment Carlito's Cabana.
After signing with WWE, Anderson made his debut on the Smack Down! In September 2006, he captured his first and only title with the company, the United States Championship, and would hold on to it for a month.
The following year at Wrestle Mania 23, Anderson won the annual Money in the Bank ladder match, a contract, which guarantees a match for one of WWE's then three world level championships. He returned to the independent circuit before signing a contract with TNA in 2010, which he was fired from TNA in 2016 and would return to the independent circuit for a second time.
Ultimately, Kennedy lost the match and the United States Championship to Benoit after submitting to the Crippler Crossface following a distraction by The Undertaker, which also marked Kennedy's first loss via submission.
In November 2006, Kennedy joined forces with Montel Vontavious Porter (MVP) in matches against The Brothers of Destruction (Undertaker and Kane) in various combinations. , Kennedy and MVP lost to the Brothers of Destruction three times.
During his early career, Anderson made some appearances on NWA Total Nonstop Action's secondary television program, Xplosion.Kennedy also created an ongoing mini-feud with Smack Down! 's No Mercy, defeating Hardcore Holly and injuring Holly's ribs during the match. , Kennedy faced Eddie Guerrero to compete for a spot on Smack Down! He lost the match when Guerrero tossed him a steel chair and played possum, a move which Guerrero had made famous. In retaliation, Kennedy struck Guerrero over the head with the chair after the match.ring announcer Tony Chimel, based on Kennedy believing that Chimel's announcing was not done well enough or with sufficient respect, and therefore performing his own introductions or forcing Chimel to introduce him again. The groggy referee turned around and saw Guerrero on the ground with Kennedy holding the chair, and consequently disqualified Kennedy, awarding the place on Team Smack Down! Kennedy accepted the challenge and won the match by disqualification, however, he suffered a severe injury during the match after being thrown headfirst into the steel steps, resulting in an exposed cranium laceration which required twenty stitches to close. , Kennedy announced that he wanted to move over to Raw, as Smack Down! , Kennedy, now with a win over The Undertaker, again stated his desire to move to the Raw brand.Kennedy and MVP continued to feud with the brothers, with MVP feuding with Kane while Kennedy challenged the Undertaker to a match at Survivor Series, which was later announced as a First Blood match.Kennedy won the match after MVP turned on him and aimed for his head with a steel chair, but missed and hit the Undertaker instead, leaving him bleeding.