At the age of sixteen, he wrestled in the opening match of a World Wrestling Federation house show in Calgary, teaming with his cousin, Harry Smith, against Andrew Picarnic and T.J. Wilson.
In 2005, he made several appearances with WWE, wrestling in dark matches, where he was defeated by Harry Smith and working as an enhancement talent on Velocity, teaming with JD Michaels against The Basham Brothers in a losing effort.
On April 1, 2006, Hart and several of his relatives attended the induction of his uncle Bret into the WWE Hall of Fame.