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Andrew Jackson (1829–1837)

Jackson was the first president to leave behind full-fledged doodles from his time in office. This drawing dates from 1833. Although Jackson’s immediate predecessor, John Quincy Adams, had kept a pet alligator in the White House, the animal was more commonly associated with Jackson’s military exploits. An 1828 campaign song, “The Hunters of Kentucky,” celebrated Jackson’s heroics at the Battle of New Orleans, in 1815, noting that in his brigade, “Every man was half a horse / And half an alligator.”

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Rutherford B. Hayes (1877–1881)

Hayes drew this woman’s face in his “Diary of a Deferred Wedding Journey,” recounting the details of a holiday he took with his wife, Lucy Webb, eight years after their 1852 marriage.

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Theodore Roosevelt (1901–1909)

Roosevelt’s boisterous brood of six, to whom he often wrote “picture letters,” included Ethel (ten years old in 1901), Archie (seven), and the youngest of the Roosevelt litter, Quentin (four). The boys developed a reputation for mischief. On one occasion, Quentin drove his toy wagon through a full-length portrait of First Lady Lucy Webb Hayes. TR was more often amused than angry.

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Warren G. Harding (1921–1923)

Harding is considered one of the worst presidents in American history. The Teapot Dome scandal stood as the benchmark for presidential sleaze until Watergate. But during his presidency he was seen as a handsome, grand-living embodiment of the Roaring Twenties—an image reflected in the energetic Art Deco aesthetic of his doodles.

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Herbert Hoover (1929–1933)

Trained as an engineer, Hoover was one of the most prolific presidential doodlers. His pictures are consistently geometric, intricate, and clever in the way they link disparate parts into a larger whole. But while his doodles hinted at elaborate and expansive visions, they never included any people. This failure to take human beings into account was all too evident in his slow reaction to the Great Depression.

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Franklin D. Roosevelt (1933–1945)

FDR’s drawings as president were mostly related to his hobbies: genealogy, stamp collecting, ships, and fishing. After Prohibition was repealed, in 1933, the Department of the Interior established a company to promote economic development in the Virgin Islands. Interior Secretary Harold L. Ickes was tasked with choosing a name and a label for the company’s rum. He proposed “Peg Leg Rum,” but FDR balked. They ultimately chose a blander name: “Government House.”

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Dwight D. Eisenhower (1953–1961)

More than any other president, Eisenhower doodled on agendas, memos, and other official documents. This agenda, from June 28, 1954, didn’t list the crisis in Guatemala as an item for discussion, but Eisenhower did. The day before, CIA-backed forces had deposed the government of Jacobo Arbenz in favor of a regime that was more pro-American (or at least more pro–United Fruit Company). With Guatemala clearly on his mind, the president sketched himself as a trim young man with big gunboats backing him up—a strong leader restoring order to the strife-torn Latin nation.