Doane made his professional wrestling debut in 2001 at the age of fifteen. He started his professional wrestling career in the New England area under the name "Broadway" Kenn Phoenix He was later trained by professional wrestler and trainer Killer Kowalski. After being contacted by World Wrestling Entertainment (WWE), he was asked to make appearances for their developmental territory Ohio Valley Wrestling (OVW).

After two years in OVW, where he won the OVW Television Championship, Doane debuted on Raw as a member of the Spirit Squad. The Squad became closely associated with The McMahons and feuded with DX, and Ric Flair. Kenny and Mikey won the World Tag Team Championship on the Raw after WrestleMania 22 from Kane and The Big Show. Under the Freebird rule, any combination of the 5 members could defend the titles. They held the titles for 216 days until they lost them to Flair and Roddy Piper at Cyber Sunday.

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