As a business entrepreneur, Childress has become one of the wealthiest men in North Carolina.
Childress's career in NASCAR's top levels started auspiciously as a drivers' strike at Talladega Superspeedway left NASCAR President William France Sr. looking for replacement drivers. Richard Childress retired from driving in 1981 after Rod Osterlund sold his NASCAR team. Richard Childress chose to retire and put Earnhardt behind the wheel of his car, complete with Wrangler Jeans sponsorship.
In the mid-1990s, Childress began expanding his racing empire, fielding entries in the Busch Series and Craftsman Truck Series. The team won the 1995 Craftsman Truck Series championship with driver Mike Skinner in the series' first season. He also expanded to a two-car operation in what is now known as Nextel Cup, with driver Skinner driving the. In the first part of the 2000s, he expanded to three cars, with the #30 car driven by Jeff Green.
With Harvick having won the Busch Series championship in 2001, Richard Childress Racing became the first team in NASCAR history to win all three of NASCAR's national championship series.
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