What History Tells Us About Trump’s Reelection Chances

Will Donald Trump run for the White House again in 2024? The possibility looks likely to roil Washington over the next few years—complicating life for other Republican hopefuls and creating a confounding set of challenges for the GOP’s political-operative class.

But for all of the 45th President’s norm-breaking, there’s nothing unprecedented about a former holder of that office angling for a return engagement. Unfortunately for Trump, it’s also a trick that only one evicted White House tenant has ever pulled off: Grover Cleveland, who lost his lease in 1888 despite winning the popular vote. As the First Couple prepared to vacate the premises, the President’s wife, Frances Cleveland, reportedly told the household staff “to take good care of all the furniture and ornaments in the house,” pending their return. Sure enough, in 1892, that’s just what happened.

Other comeback attempts, alas, weren’t so successful. Here’s a roundup.

Martin Van Buren

The Democrat lost his bid for reelection in 1840. Eight years later, as the politics of slavery roiled the electorate, he sought a comeback as a candidate of the Free Soil Party, which opposed slavery’s spread. Van Buren won 10 percent of the popular vote—but zero electoral votes.
 

Millard Fillmore

A VP who became POTUS after the death of Zachary Taylor, Fillmore wasn’t even nominated by his own party at the end of his partial term. In 1856, as his Whig Party came apart over slavery, he was the candidate of the anti-immigrant Know Nothing Party. He won more than 20 percent of the popular vote but only eight electoral votes.
 

Ulysses S. Grant

Grant didn’t try for reelection after his administration’s second term, saying, “I do not think I could stand it.” But the next time around, he changed his mind, and his name was on the ballot at the GOP convention four years later. Despite predictions that only an act of God could prevent the war hero from snagging the nomination, the bias against a third term was strong and Grant pulled back. Another ex-general, James Garfield, won the nomination—and the presidency.
 

Theodore Roosevelt

Roosevelt chose not to run again after his second term, instead supporting his friend William Howard Taft. Four years later, feeling his successor had failed to pursue Roosevelt’s progressive goals, Teddy tried to win back the GOP nomination. When that didn’t work, he ran as a candidate of the Progressive “Bull Moose” Party. The divided vote helped elect Woodrow Wilson. The friendship didn’t last, either.
 

Gerald Ford

Ford, who had taken over after Richard Nixon’s resignation, lost a close one to Jimmy Carter in 1976. He thought about entering the ring in 1980, then flirted with accepting the vice-presidential nomination under Ronald Reagan, something that would have been truly unprecedented. And maybe it was unprecedented for a reason: As the political class chattered about a Reagan/Ford “co-presidency,” Reagan soured on him. He picked George H.W. Bush instead.

This article appears in the September 2021 issue of Washingtonian.

Tevi Troy