Oakes was one of the leading midget car drivers on the West Coast for more than 20 years, with many top finishes at the famed Gilmore Stadium. He also was a participant at the famed Legion Ascot Speedway in Los Angeles in the mid-1930s. Oakes was near the end of his driving career when he won the USAC Pacific Coast Midget title in 1959.
When Jim Hurtubise came within an eye-blink of turning the first 150-mph laps at Indianapolis as a rookie in May 1960, Oakes was his chief mechanic. Hurtubise was named Rookie of the Year.
Oakes had a second Rookie of the Year with fourth-placed Johnny White in 1964, while others who drove Oakes-prepared cars in the "500" were Troy Ruttman, Paul Goldsmith, Mike Magill and Bill Cheesbourg.
Never able to qualify for the "500" as a driver in attempts from 1952-55, Oakes was bumped from the field in 1954 and made an incomplete attempt in 1952 with a Ferrari which had been turned down by Johnnie Parsons. Oakes was befriended by two-time Formula One World Champion Alberto Ascari, who invited Oakes to stand by as a relief driver at Indy. Ascari's Ferrari was eliminated before a single pit stop could be made.
Oakes was passionate about racing to the very end and was still attending races in fairly recent years.