[2] His brother, Wilmer Wesley Young, studied journalism at the University of Wisconsin and founded its student newspaper, The Daily Cardinal.

Also that year, he began working for a succession of Chicago newspapers including the Evening Mail, the Daily News, and the Tribune.

Following a long convalescence, he joined the Chicago Inter-Ocean (1892), to which he contributed political cartoons and drawings for its Sunday color supplement.

Young started out as a generally apolitical Republican, but gradually became interested in left wing ideas, and by 1906 or so considered himself a socialist.

He began to associate with such political leftists as John Sloan and Piet Vlag, with both of whom he would work at the radical socialist monthly The Masses.

He became politically active, and by 1910, racial and sexual discrimination and the supposed injustices of the capitalist system became prevalent themes in his work.

He explained these sentiments in his autobiography, Art Young: His Life and Times (1939): I am antagonistic to the money-making fetish because it sidetracks our natural selves, leaving us no alternative but to accept the situation and take any kind of work for a weekly wage [...] We are caught and hurt by the system, and the more sensitive we are to life's highest values the harder it is to bear the abuse.

The companies successfully petitioned the Federal government to declare martial law under a military tribunal, an egregious act according to the editors of the Masses.

Young's cartoon and Max Eastman's editorial, published in the same issue, claimed the AP willfully suppressed the facts to aid the coal companies.

He also served as an illustrator and Washington correspondent for Metropolitan Magazine (1912–1917) until it released him due to his outspoken anti-war sentiments.

In October 1917, the federal government charged Young, Max Eastman, John Reed, Floyd Dell, Merrill Rogers and a one-time contributor with conspiracy to impede enlistment under the Espionage Act.

When their trial began in April the next year, Young was asked to justify his cartoon "Having Their Fling", in which four men—an editor, a capitalist, a politician and a minister—are depicted dancing in orgiastic bliss as Satan leads a band of war implements.

Prosecutor Barnes, wrapped in an American flag and giving a moving speech, told a story of a dead soldier in France.