Winfield was born in Springfield, Missouri, in 1927.
His family moved to Modesto, California, in 1929, where he grew up.
He was first exposed to cars when his older brother, Glenn, opened a wrecking yard.
In 1942, he bought his first car for $75, a 1928 Ford coupé, and promptly added a radio antenna with foxtail, despite it having no radio.
Later that year, the brothers opened Winfield Used Cars in Modesto.

His second car was a 1930 Ford, powered by a 1937 flathead.
Winfield was born in Springfield, Missouri, in 1927. His family moved to Modesto, California, in 1929, where he grew up. He was first exposed to cars when his older brother, Glenn, opened a wrecking yard. In 1942, he bought his first car for $75, a 1928 Ford coupé, and promptly added a radio antenna with foxtail, despite it having no radio. Later that year, the brothers opened Winfield Used Cars in Modesto. 
His second car was a 1930 Ford, powered by a 1937 flathead.
Gene Winfield