Jeff Gordan – Oldsmobile Super 88 Convertible 1952 – $128k

As a former stock car race driver, Jeff Gordan drove the No. 24 Chevrolet in the NASCAR Winston Cup Series. He even served as a substitute driver for fellow driver Dale Earnhardt Jr in 2016. He started his racing career in the Busch Series, winning three races. Gordan is no ordinary racer as he won the Cup Series four times, in 1995, 1997, 1998, and in 2001. Now, he works primarily as a NASCAR announcer, offering his insights every now and then.

Perhaps the best car in his collection is an Oldsmobile Super 88 Convertible, released in 1952. This vehicle is reminiscent of everything 1950s and so Gordan did not hesitate to part with $128,000 of his investment money for it. He also restored it to its original condition. Considering he drives modern cars for a living, a classic car in the garage is definitely a welcome change. Plus, he probably liked working on the restoration of the vehicle.