Gail became interested in racing in 1958, after he and some friends went to watch the races at the Speedrome. He went home and built his first race car. In 1958, sponsored by the Brew, Gail won his first feature at the "Drome". With the Brew still his sponsor, Gail won two features in 1959. In 1960, with Ron Zimmerman as co-owner and the Brew his sponsor, he was racing three nights a week and Gail won 10 features and sixteen heat races. 1961 brought the Big Boy sponsored car with Ron Zimmerman as co-owner. He won nine features, 24 heat races and was second in the final point standings at the Speedrome. In 1962, the team won 10 features, 40 heat race wins and became the track champion. That year also gave him a feature win in the Ambrose super modified, driving in the place of Sammy Sessions. He also won the super modified heat race and pursuit the same night.
In 1963 the Cobb/Zimmerman/Big Boy team won six features and 13 heat races. From 1964 Gail owned his own car with Phil Anible as his mechanic. He won 15 features, which included a win at Kalamazoo. In 1966 he won the Memorial Day Championship at the Speedrome and had tow feature wins at Kalamazoo. He also won the Spring Stock Car Championship at Berlin in 1967. In 1969 and 1970, with car owner Jim Dantema and sponsored by J.D. Speedshop, Gail won a feature at Kalamazoo.
From 1971 to 1974, driving a 6-cylinder '66 Mustang, he won nine features between Kalamazoo, Berlin and Galesburg. He also won a feature at South Bend in Indiana in 1974. In 1976 to 1979, in partnership with Bill McGowen, Gail won two features at Berlin, two features at Galesburg and one feature at Mottville. In 1978 standing in for Jack Gritter, he won the feature at I-96 Speedway. In 1980, driving for Bob Marz he won a feature. The next year driving his own car he took a 50-lapper at Galesburg. The following year, driving a sportsman car for Bob Lyons, Gail won four features and 13 heat races. In 1985 he ran one race in August at Kalamazoo and won the feature. In 1986 running the sportsmen class at Kazoo, Gail won two features, one being the Bob Berry Memorial.
Gail switched to the Zoo-Mods for 1987 and won the first ever feature in that class, plus the Race of Champions in August. In July of 1988 he won another Zoo-Mod feature. in 1988, 1989, and 1990 Gail entered the Super Shoe Nationals at Kalamazoo Speedway, and with the help of Scott Baker he won the feature all three years. In 1991 he won the Michigan State Championship Sports Stock feature at Kazoo.
Gail has at least 87 feature wins and still competes occasionally. Gail's most memorable night was the time he drove the Ambrose super modified for the first time and won the heat, pursuit and feature. He also drove his regular sportsman car that night and won the heat, pursuit and feature as well.