Unlike the 2020s The Pulitzers had an Editorial Cartooning category in the 1920s.
Rollin Kirby took three of the first seven Pulitzers awarded in that journalism division.
The inaugural honor went to Rollin Kirby, who worked for an array of New York newspapers and magazines. He won the award for his depiction of the victims of the Russian famine of 1921.
It was the first of three Pulitzers that Kirby would capture in his career, which spanned over forty years.
His first Pulitzer-winning cartoon, The Road to Moscow, appeared in the World on Aug. 5, 1921. He struck again on Oct. 5, 1925 with News from the Outside World, which portrayed countries who were not part of the League of Nations, and earned him his second Pulitzer.
Kirby then won a third Pulitzer for Tammany, which appeared on Sept. 24,
1929 and employed the Tammany depictions of the acclaimed Thomas Nast from decades before. The cartoon derided Republicans who blasted Tammany and ignored their own corruptions.
Amazingly two of the three cartoons could, with minimal adjustments, be applied to situations today – Russia cutting off grain exports from Ukraine and Republican hypocrisy over any number of topics (yeah, Democrats too).
[* Other three-peaters: Edmund Duffy, Herbert l. Block, Jeff MacNelly, and Paul Conrad.]
further reading: A 1940 American Artist piece on the cartoonist via Larry Rippee and Molly Rea.