Richard Childress, a celebrated figure in NASCAR and a highly respected businessman, opened up about his early life in a dramatic retelling of his experiences with bootlegging, a chapter that shaped his future before he launched his racing career. The intense Richard Childress bootlegging story exposes the risky path he took as a teenager in North Carolina before stepping onto the tracks of professional stock car racing.
Early Ambitions and a Dangerous Detour
Growing up with big aspirations, Childress began working at the Bowman Gray stadium, initially making money by selling peanuts, but soon sought grander opportunities. Choosing not to finish high school, he looked for alternative ways to achieve his dreams and, at just 16 or 17 years old, landed a job at an all-night gas station. This job drew him into an underground world far riskier than it appeared on the surface.
The gas station was a hub for bootleggers from Wilkes County, who transported illicit liquor from the mountains to Winston-Salem. Childress’s responsibilities quickly moved beyond fueling cars; he was tasked with delivering illegal alcohol to hidden drink houses scattered throughout the region while the bootleggers took care of other, less savory business.
A Night That Changed Everything
Childress was paid for each successful delivery, and for a while, the operation ran smoothly. That changed dramatically one night during a delivery run. In a later interview with Dale Earnhardt Jr., he described the chilling event that steered his life in a new direction.
“There was a killing, and I was in the right room. I heard the gun go off, and I ran. So, that’s drink houses back up there on Old Patterson Avenue — the roughest part of town. It was something. I can still see some of that.”
The murder in the heart of Old Patterson Avenue shook Childress deeply, leaving an indelible mark on his memory. Realizing the escalating danger, he resolved to sever ties with bootlegging and pursue a safer, if equally ambitious, path forward.
Shifting Gears to Racing
With his sights set on change, Childress redirected his efforts to racing, eventually seizing a pivotal moment at the inaugural Talladega Superspeedway race in 1969. The event was unique—several drivers from the prestigious Grand National Series refused to participate, citing safety risks. William H.G. France, then leader of NASCAR, turned to Childress and other Grand American drivers to fill the gaps left by the absent racers.
France’s promise of significant rewards was honored. Childress finished 23rd and earned $7,500—money that became his initial stake in what would eventually become Richard Childress Racing, a powerhouse in modern NASCAR circles.
Legacy Carved from Turbulent Beginnings
The Richard Childress bootlegging story is a remarkable tale of survival and transformation. From delivering illegal liquor during his teenage years and witnessing a tragic killing, to racing against the odds and building an iconic business legacy, Childress’s path illustrates the risks, resilience, and bold choices that defined his journey. The impact of his early life lessons continues to shape Richard Childress Racing, showing how one man’s escape from a violent past paved the way for a legendary career in motorsports.
Richard Childress has tales from his days as a real-deal bootlegger. 🥃 #BestOfDaleJrDownload@DaleJr | @RCRracing pic.twitter.com/7Wrosk7dmh
— Dirty Mo Media (@DirtyMoMedia) December 31, 2025
