Grant E. Hamilton, The Judge vol. 7, 31 - 1885
Cartoon from the magazine "The Judge". "Democracy" is portrayed as the devil holding a bucket labeled "Bourbon Principles" and a paintbrush (in which appears a profile caricature of Grover Cleveland), both dripping red paint with which he plans to "paint the town"; he is standing on a wall overlooking a view of Washington, D.C. showing mostly government buildings, some already flying red flags: "Pension Dep't", "White House", "U.S. Treasur", "War Dep't"
What is the origin of the expression 'to paint the town red'?

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