Whitt won the Rookie of the Year title in NASCAR's Southwest Touring division in 2002, and made his Craftsman Truck Series debut in 2003, driving the #38 Chevrolet Silverado for Clean Line Motorsports, a team his father owned. He finished thirteenth in his debut, and ran six additional races that season, his best finish a thirteenth at California Speedway. In 2004, Whitt and his team ran the Truck Series full-time with sponsorship from McMillin Homes and running Ford F-150s. Despite not finishing any higher than 12th in his rookie season, Whitt finished 19th in the final standings.
During the 2005, his team was purchased by Jeff Hammond, with the name change to Red Horse Racing and switched to Toyota. He won his first race at Memphis after taking the lead from a spinning Ron Hornaday on the last lap. He was dismissed from the team at the end of the season, leaving him out of a ride. He opened the season running with CLR Racing in ARCA at Daytona International Speedway, before forming his own part-time team. He attempted his first NEXTEL Cup race at Phoenix International Raceway with CJM Racing and qualified but finished 43rd. He was scheduled to run with CJM for 12 races in 2007, but those plans changed when Whitt was released from the ride. Whitt drove one race later that season for Red Horse at Atlanta, where he finished twenty-third.
Midway through 2008, he signed to drive for Specialty Racing in the Nationwide Series.
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