Brian O’Leary is TCA’s 2004 Company Equipment Driver of the Year.

On a bright, warm Colorado day in early February, Brian O’Leary is hard at work solving a trucking problem. The trucker from Fort Collins is using his Saturday to stuff a Dodge Prowler, an Audi A8 and a Jaguar XJ8R into the back of his 48-foot reefer.

“I need another six inches to fit the Jaguar in,” he says at his shop in the shadow of the Colorado Rockies. The problem may sound a little unusual for a reefer hauler, but long hours at work in and around trucks is not.

The slim, slightly graying driver was born to be a trucker. His father, (John R. O’Leary) drove for nearly 40 years, and when he died in 1973, Brian O’Leary, just 21 years old, stepped into his father’s shoes and slipped behind the wheel of the same truck. Three decades later, O’Leary has reached the pinnacle of his trucking career, named as the 2004 Company Equipment Driver of the Year by the Truckload Carriers Association and Truckers News.

O’Leary has the same sandbox stories of Tonka trucks and big rig dreams as most second-generation truckers, but his climb to the top started with a high school job washing and moving trucks at a UPS facility in Peoria, Ill., where he was raised. After his induction into the Air National Guard, O’Leary, then 20, started shuttling loads of meat, candy and perishables from Peoria to Chicago and the Quad Cities. His dad, driving a bright yellow and orange Kenworth, visited on trips through Illinois as a company driver for Monfort of Colorado, a large beef and cattle company.

This early exposure to trucks and his dad’s visits set the stage for a 34-year trucking career that includes 3.5 million miles without an accident, ticket or hours-of-service violation. Along the way, he has picked up accolades from the Colorado Motor Carriers Association, the city of Fort Collins and the Lava Soap Co.