If Trump wins reelection, he would be the second president in U.S. history to serve non-consecutive terms.
The first was Grover Cleveland, who did two stints in the White House from 1885-1889 and 1893-1897.
How did that happen?
A primer on the nation's 22nd and 24th president
Cleveland, a lawyer, entered politics in his forties as an anti-corruption reformer. He was elected mayor of Buffalo, N.Y., in 1881 and the state's governor three short years later.
Cleveland was nominated as the Democratic Party's presidential candidate in 1884 and overcame a sex scandal to narrowly defeat his Republican opponent, Sen. James Blaine of Maine. He was the first Democrat elected after the Civil War, which ended in 1865.
His first term was marked by several major moments, including the deadly Haymarket Riot of 1886 in Chicago, which became a symbol of the struggle for workers' rights, and the passage of the Interstate Commerce Act in 1887, which established federal regulation of an industry (railroads) for the first time.
Cleveland, elected as a bachelor, also got married during his presidency, the only president to do so in the White House.
But he also made some decisions that angered his critics, like vetoing private pension bills for Civil War veterans and money to distribute seed grain to drought-stricken farmers.
He ran for reelection in 1888 but lost to Republican candidate Benjamin Harrison — a Union Army colonel during the Civil War, and the grandson of former President William Henry Harrison.
Cleveland's reelection campaign was poorly run on many levels, presidential historian Troy Senik told History.com.
"He began the race without a campaign manager; delegated most of the electioneering responsibilities to his running mate, Allen Thurman, who, at the age of 74, was not healthy enough to withstand the rigors of campaigning; and based the entire race around his proposal to reduce tariffs, which divided his own Democratic Party and unified the Republicans in opposition,” Senik said.
Cleveland won the popular vote — 48.6% to 47.9% — but lost the Electoral College vote. He moved to New York City and practiced law.
So what lured him back to the campaign trail?
Barbara Perry, co-chair of the University of Virginia Miller Center’s Presidential Oral History Program, told History.com that Cleveland didn't intend to run again after his first term, but was increasingly dissatisfied with his party's populist drift and concerned that another nominee would "draw the party towards the kind of cronyism that he had fought so hard against."
Notably, she said, his decision to run again predates the modern primary system — so didn't involve voters the same way it would today. He was nominated in 1892 and ran against Harrison once again.
This time, with the country on the brink of an economic crisis and newly receptive to his position on reducing tariffs, Cleveland won in a landslide.
His second term was also dominated by economic and labor issues, from the economic depression known as the Panic of 1893 to the Pullman Strike, which disrupted rail traffic throughout the Midwest and marked the first time the federal government used an injunction to break a strike (it also led to the creation of Labor Day as a conciliatory gesture).
Support for Cleveland from his own party dwindled throughout his term. After leaving the White House he retired to Princeton, N.J., where he lived until his death in 1908.
While Cleveland was the only president who succeeded in winning non-consecutive terms, he wasn't the only one who tried.
Martin Van Buren, who served from 1837 to 1841, tried running as a third-party candidate in 1848. Millard Fillmore, who served from 1850 to 1853, ran again in 1856. Theodore Roosevelt, who left the White House in 1909, ran unsuccessfully for a third term in 1912.
Over a century later, Cleveland remains in a club of one — and Trump is angling to join.
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