In May 1867, after conflict with editor George William Curtis, Nast left Harper’s Weekly to paint 33 9 x 12 foot pictures and incorporate them into a travelling panorama show called the Grand Caricaturama. When it failed in March 1868, he accepted a job as head cartoonist for the start-up Illustrated Chicago News. It too failed after eight issues and Nast returned to Harper’s.

In its third issue, Nast previewed the forthcoming 1868 Presidential election. “Prince” Columbia was looking over eighteen possible candidates, but only Grant’s dainty foot would fit his glass slipper. Other potential Republicans Ben Wade and Ben Butler had relatively small feet, but looked as dismal as their prospects. Schuyler Colfax, who would become Grant’s Vice President, also was prominent.

Among Democrats, George McClellan wore a dunce cap in front of Columbia, while “King Andy” Johnson’s huge feet, labeled “My Constitution” and “My Policy” were the worst fit of all. The most likely Democratic nominee at that point in time was Chief Justice Salmon Chase, sitting on Grant’s right with his feet almost covered by his judicial robe.

Nast’s knowledge and subtlety with regard to the other candidates was prescient. He placed George Pendleton, a diehard Copperhead who had been McClellan’s running mate in 1864, just above McClellan. Sure enough, Pendleton led on the first fifteen ballots. The leader on the sixteenth was Union General Winfield Scott Hancock (who would become the Democratic nominee in 1880). Eventually, Horatio Seymour, who Nast stationed furthest from the Prince to emphasize the odds against him, won on the twenty-second ballot.