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Donald Trump, Grover Cleveland, and the History of Trying to Win Back the White House

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Donald Trump, the 45th President of the United States (2017-2021), announced on Tuesday night that he’s running for a second term in 2024.

“America’s comeback starts right now,” the real estate mogul and reality TV star told the audience at his Palm Beach, Fla., private club Mar-a-Lago. Trump, who tried to overturn the results of the 2020 election and has refused to acknowledge he lost, referred to his time out of office as just a “pause.” (Fact-checkers counted 20 false and misleading claims in the speech, which ran over an hour.)

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Read more: Trump’s 2024 Announcement Makes Clear He Has No Idea Why He Lost

Trump is not the first President to launch a comeback campaign. A handful of presidents tried to get back into the White House and failed. Some examples include Martin Van Buren in 1844 and 1848; Millard Fillmore in 1856; Ulysses S. Grant in 1880, in the era before term limits and four years after serving a second term; and Teddy Roosevelt in 1912, with the third-party Progressive Party, after losing the Republican nomination.

But Democrat Grover Cleveland is the only president to serve nonconsecutive terms, from 1885 to 1889 and from 1893 to 1897, according to the University of Virginia’s Miller Center, which specializes in presidential scholarship. Though both were defeated in their bids for a second consecutive term, historians say that Trump faces a tougher political environment when mounting his comeback than Cleveland did.

Stephen “Grover” Cleveland—also known as “Big Steve” and “Uncle Jumbo”—wasn’t planning on running again as soon as he left office. He lost the 1888 presidential election to Republican Benjamin Harrison amid allegations of voting irregularities—and despite winning the popular vote.

According to Louis Picone, author of Grant’s Tomb and spokesperson for the Grover Cleveland Presidential Library in New Jersey, Cleveland enjoyed fishing at his house in Cape Cod and spending time with his new wife and his daughter Ruth.

Similar to Trump, Cleveland made his decision to run again after the midterm elections. He saw an opening after what Picone describes as a “bloodbath” for Republicans. Supporters of Cleveland started encouraging him to run after the 1890 midterms, which they viewed as a repudiation of President Harrison. By contrast, the 2022 election “really wasn’t this ‘Red Wave’ that was predicted,” Picone says. Many have viewed that election as a repudiation of Trump-backed Republican nominees.

Congress under the Harrison Administration was nicknamed the “billion dollar Congress” because it was the first time that a billion dollars in federal dollars was spent. Cleveland was a fiscal conservative, dedicated to lowering tariffs, solidifying the gold standard, and reducing public spending. During the Gilded Age, when corruption in politics was rampant, Cleveland had the reputation of representing honesty in politics.

Cleveland didn’t have to campaign very hard, easily winning his party’s nomination. Backlash to high tariff policies and a wave of violent labor strikes at silver mines in the summer of 1892 made voters think Harrison didn’t have enough of a handle on economic policy.

However, he didn’t have an easy time of it when he was back in office. The Panic of 1893—the worst economic depression America faced at that point—colored his legacy. But towards the end of his life, “he regained stature as an elder statesman and a throwback to an earlier time,” says Picone.

Whether Trump is able to follow Cleveland’s success in 2024 remains to be seen—but he faces substantial political headwinds at the moment. Cleveland was broadly welcomed back by the Democratic Party, and was thought to be the most electable candidate.

Trump may be in for a harder fight to his party’s nomination. Following a much weaker than expected 2022 Midterm Election showing, there are reports that top GOP donors are eyeing candidates like Florida Governor Ron DeSantis.


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