York began working for the Chicago Tribune and Nashville Banner throughout the 1930s before joining the Louisville Times in 1937.
As a political cartoonist, York spent the majority of his career with Louisville apart from a stint with the United States Army Air Forces during World War II.
[1][2] While completing his studies, York was trained by various people including Ding Darling and Vaughn Shoemaker.
[3] York began working in cartoons with the Chicago Tribune as an assistant cartoonist for Carl Ed from 1930 to 1935.
[4][5] While with the Louisville Times, York worked as a political cartoonist from 1937 to 1974 with the exception of World War II.