sixteen finishes between 11th-18th, leading to a seventeenth-place points finish and runner-up to Brendan Gaughan for NASCAR Craftsman Truck Series Rookie of the Year. The next season, he grabbed his first career pole at Lowe's Motor Speedway and had a tenth-place run at Kansas Speedway, garnering a 14th-place finish in the championship standings. He switched over to Bill Davis Racing in 2004. He had a best finish of tenth and finished 22nd in points. In 2005, he won two consecutive poles, and had his first top-five finishes. Lester raced in his first Nextel Cup race in the Golden Corral 500 at Atlanta Motor Speedway, driving the No. 23 Waste Management Dodge Charger for Davis in 2006. The race was supposed to be run on March 19, but was postponed for a day due to rain. He qualified 19th, becoming the first African-American to make a Cup race since 1986, and the sixth in series history. He finished 38th, six laps down. He ran another race that season at Michigan, finishing 32nd. He later DNQed at California after spinning in qualifying. After failing to finish in the top-ten in 2006, Lester departed Davis to drive the No. 15 Billy Ballew Motorsports Chevy. His best finish was an eighth at Kentucky, when he stepped out of the truck due to sponsor problems. After he was unable to find another ride in NASCAR, he left in 2008 to return to sports car racing. On February 26, 2021, Lester announced on NASCAR Race Hub that he would be coming out of retirement to compete in the Truck Series race at his home track of Atlanta, which was also the same track where he made his Cup Series debut at in 2006. The team was revealed as David Gilliland Racing on March 12, with local Ford dealerships and Camping World as his sponsors. He finished 36th. Return to sports cars In 2008, Lester drove the No. 3 Riley Daytona Prototype for Southard Motorsports in the Grand-Am Rolex Sports Car Series, partnering with Shane Lewis. He moved to Orbit Racing for 2009, finishing 3rd at the summer Daytona race. The next year, Lester moved to a new team in Starworks Motorsport driving the No. 7 BMW Riley for the full season, finishing 17th in points. For 2011, Lester moved to the GT category with Autohaus Motorsports and their Chevrolet Camaro team. On May 14, 2011, Lester