On Nov. 5, 2024, Donald Trump won a second non-consecutive term in the White House. Trump’s triumph drew comparisons to the 1892 re-election of Democrat Grover Cleveland — the only president other than Trump to regain the White House after he previously lost re-election. Cleveland won in 1884, lost in 1888 and recaptured the presidency in 1892.
Like Trump, Cleveland maintained popularity within his party despite losing. This support enabled Cleveland to cruise to the 1892 nomination, and he capitalized on Republican struggles to recapture the White House. Yet, while his second election was a triumph for the Democratic Party, it ended up demolishing the party for a generation. Cleveland’s example offers a cautionary tale for Republicans in 2024: a second Trump administration involves as many risks as possible benefits.
Grover Cleveland would have been an unlikely candidate for president in any period of American history other than the one in which he served. Born in 1837 in New York, he worked as a lawyer in Buffalo for much of the 1860s and the 1870s, a period during which the state’s Democratic Party became nationally renowned for corruption because of the rule of the Tammany Hall machine.
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