Early career Lester began racing in the road course circuits, running in the
SCCA and
IMSA series. He made his IMSA debut in 1990 at
Sears Point International Raceway, qualifying ninth and finishing first in a
Chevrolet Camaro. He also picked up a victory that year in an endurance race at
Sears Point. In 1990, he began running the SCCA, running an unsponsored
Oldsmobile Cutlass for
Rocketsports at
Portland, and one race for
Tom Gloy at
Mid-Ohio. He did not race professionally again until 1996, running SCCA events at
Watkins Glen,
Elkhart Lake, Wisconsin, Sears Point, and
Reno, Nevada. He competed in the
24 Hours of Daytona in 1998 and 1999, finishing fifth and tenth, respectively.
NASCAR In
1999, Lester became the first African-American to run a
Busch Series race, when he ran at Watkins Glen in the No. 8
Dura Lube Chevrolet Monte Carlo owned by
Bobby Hillin Jr. He started 24th and ran near a top-ten most of the day before an accident relegated him back to 21st. The next season, he made his Craftsman Truck debut at Portland, starting 31st and finishing 24th in the No. 23
Red Line Oil truck owned by
Team 23 Racing. He also competed against
Bobby Norfleet in that race, marking the first time in NASCAR two African-Americans competed in the same race. He ran five races the next season in the No. 4 for
Bobby Hamilton Racing, his best finish an eighteenth at
Phoenix International Raceway. In
2002, Lester ran in the Craftsman Truck series full-time for Hamilton. While he did not finish in the top-ten, he had sixteen finishes between eleventh-eighteenth, 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 fourteenth place finish in the championship standings. Lester 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 nineteenth, 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 third 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 seventeenth in points. For 2011, Lester moved to the GT category with Autohaus Motorsports and their
Chevrolet Camaro team. On May 14, 2011, Lester made sports car history by becoming the first African-American driver to win in any Grand-Am division. Fittingly, Lester won at the
Virginia International Raceway, located close to the home of NASCAR's first African-American winner,
Wendell Scott. ==Personal life==