Under the training of Rockin' Randy and the NAWF, James started his career, alongside CM Punk, Colt Cabana, Brad Bradley and Adam Pearce.
James won the Ohio Valley Wrestling Southern Tag Team Championship from The Untouchables (Domino and Deuce Shade) on April 5, 2006, with tag team partner Roadkill.
After losing the tag team titles to Neigbourhoodie and Shad Gaspard on May 27, 2006, he was called up to th main WWE roster.
He formed a tag team on Smackdown! with Idol Stevens. They were managed by WWE Diva Michelle McCool, introduced as one of her favorite "Teacher's Pets."
They defeated Funaki and Scotty 2 Hotty with the help of McCool in their debut match. In the following weeks, they feuded with Paul London and Brian Kendrick & "The Pitbulls" Kid Kash & Jamie Noble.
In March, 2007, the team of Idol Stevens & K.C. James broke up, after their manager Michelle McCool got injured.
James was sent back to OVW, starting another tag team, this time with Cassidy O'Reilly, going as "The James Boys". The James Boys went on to defeat The Major Brothers to capture the OVW Southern Tag Team Championships.
James once again started wrestling dark matches for WWE around September, 2007. He went on to defeat Colt Cabana to become the OVW Television Champion on November 17, 2007.