It all started with an insult. During Andrew Jackson's 1828 presidential campaign, his political opponents labeled him a "jackass." Stubborn as he was, Jackson co-opted the insult and began putting a donkey on his election posters. For the rest of his career and even into his retirement, newspapers and cartoonists continued to represent Jackson either as a stubborn ass or struggling to control one.
Almost 40 years later, the donkey was used to represent not just Jackson, but a larger group of Democrats. In 1870, Thomas Nast, the German-born political cartoonist who gave us the versions of Santa Claus and Uncle Sam we know today, drew a cartoon for Harper's Weekly titled "A Live Jackass Kicking a Dead Lion." The donkey was a stand-in for "Copperhead Democrats" (the Northern Democrats that opposed the Civil War), and the lion represented Edwin M. Stanton, Abraham Lincoln's recently deceased Secretary of War. Nast thought of the Copperheads as anti-Union and believed the Democratic press's treatment of Stanton was disrespectful.
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