His first political cartoons appeared during the 1896 Presidential Campaign but he preferred to concentrate on non-political subjects. However, he was a great supporter of Theodore Roosevelt and the Progressive Party.
John McCutcheon moved to the Chicago Tribune in 1903 and remained with this newspaper for 43 years. He made several overseas tours and provided drawings for the books Asia (1907) and Africa (1909). He also visited the Western Front during the First World War.
McCutcheon, who married Evelyn Shaw in 1917, is often referred to as the “Dean of Cartoonists”. He won the Pulitzer Prize for his coverage of the bank crisis. This included his best known cartoon, A Wise Economist Asks a Question, which deals with the wave of bank failures that crippled the nation during the 1930s, using the squirrel as a symbol of prudence.
At the end of his career McCutcheon remarked that: "I always enjoyed drawing a type of cartoon which might be considered a sort of pictorial breakfast food. It had the cardinal asset of making the beginning of a day sunnier."
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