He won three Pulitzer Prizes, and shared a fourth with the Washington Post for coverage of the Watergate scandal.
In 1943, he joined the Army, which employed his cartooning in its Information and Education Division. After the war, he joined the Washington Post.
He coined the word "McCarthyism".
He won a scholarship to the Chicago Art Institute when he was 12. He took night classes in art while attending high school. Painting was a lifelong hobby. He dropped out of Lake Forest College after two years when he got a job with the Chicago Daily News. His editorial cartoons were syndicated almost from the start.