My last post was about past female presidential candidates who put cracks in the glass ceiling and paved the way for future women to run for national office. So let’s add to the historical comparisons for 2024 by looking at some former presidents who returned to make another run for the White House after being out of power, as Donald Trump is now doing. It’s not a long list, but it’s a unique one.
Van Buren and Fillmore: 19th century independents
Only five ex-presidents, including Trump, have ever left office and then come back later to make another bid for the highest office. Two of these campaigns took place during an eight-year span in the mid-19th century and both involved a former president who became the nominee of a third party.
Martin Van Buren and the Free Soil Party
The first was in 1848 with Martin Van Buren, who’d been elected as a Democrat in 1836 before losing his re-election campaign to William Henry Harrison in 1840.
Eight years later, with the debate over slavery roiling the country, the Free Soil Party formed with a goal of stopping slavery’s expansion. The party, made up of disaffected Democrats and Whigs, turned to Van Buren as its nominee, with a slogan of “Free Soil, Free Speech, Free Labor and Free Men.”
There was enough discontent in the nation over slavery that Van Buren won 10% of the vote in the general election. But that vote share didn’t translate to wins in any single state, so Van Buren was shut out of the Electoral College in a contest won by the Whig Zachary Taylor.
Millard Fillmore and the Know Nothings
Fast forward eight more years, and this time it was Millard Fillmore who abandoned retirement for a presidential run with a third party.
Fillmore was elected vice president under Zachary Taylor in 1848, then became president when Taylor died in office in 1850. He didn’t get a chance to run for another term in his own right, as northerners turned against him in a dispute over slavery policies and he lost a battle for the 1852 Whig nomination.
But when another election came around in 1856, the new American Party found itself looking for a leader. Popularly known as the Know Nothings, the American Party was a nativist and nationalist movement that arose in response to a wave of immigrants flooding into the country, many of whom were poor Irish Catholics. After winning several dozen seats in Congress, the party convinced Fillmore to be its 1856 nominee.
The Know Nothings ran on a slogan of “Americans to rule America.” Fillmore won nearly 22% of the popular vote, but prevailed in only one state with eight electoral votes in a contest won by the Democrat James Buchanan.
Theodore Roosevelt and the 1912 Bull Moose Party

The most successful third party campaign ever run was also led by a former president. That was the 1912 campaign of Theodore Roosevelt.
Although Roosevelt left office voluntarily by not running in 1908, he was disenchanted with his Republican successor, William Howard Taft. So he challenged Taft for the 1912 GOP nomination. Roosevelt swamped Taft by winning nine of 12 state primary contests, but with support from party leaders Taft defeated Roosevelt at the convention.
Roosevelt and his supporters then broke from the GOP and formed a new Progressive Party (which was widely known as the Bull Moose Party). That fall, the country saw a dramatic battle between three past and future presidents, as Roosevelt and Taft clashed with the Democrat Woodrow Wilson.
In the general election, Roosevelt took 27% of the ballots, finishing second in the popular vote and dooming Taft to third place. But even that only translated to 88 electoral votes, as Roosevelt and Taft split the GOP. Wilson swept to the presidency with 435 electoral votes despite winning only about 42% of the popular vote.
Grover Cleveland: The only president to win non-consecutive terms
These first three examples are all instances of former presidents returning to run a third-party campaign, so there aren’t great parallels here to what Trump is trying to do in 2024. But there is one historical comparison that does work: Grover Cleveland, who is so far the only person to win a second term in office after leaving the presidency. Notably, Cleveland is also the only one of these presidents aside from Trump to be nominated again by his party after losing a re-election campaign.
Cleveland, a Democrat, was first elected in 1884. He lost his bid for re-election in 1888 to the Republican Benjamin Harrison, but in 1892 came back to defeat Harrison in a rematch and win a second, non-consecutive term in office.
If you look at the history, there is one striking parallel between Cleveland’s and Trump’s election campaigns, and one stark difference.
The Parallel: A divided nation and narrow Electoral College victories
Cleveland and Trump both ran for president at a time when the country was starkly divided between the two major political parties and the results turned on slight differences in the Electoral College.
Trump, for instance, won in 2016 after prevailing by fewer than 78,000 votes in Michigan, Wisconsin and Pennsylvania, while Biden’s electoral win in 2020 was built on wins in Arizona, Georgia and Wisconsin by 43,000 combined votes.
Similarly, Cleveland won his first election in 1884 when he defeated James Blaine by just 1,149 votes in New York, and then he lost in 1888 when New York and Indiana narrowly flipped to Harrison. In 1892, he flipped those states and a couple of others back to the Democratic column.
The Difference: Cleveland won the popular vote, Trump did not
On the other hand, Cleveland did win the popular vote in all three of the 1884, 1888, and 1892 elections. In fact, he is one of only three presidents to win the popular vote three times, along with Franklin Roosevelt and Andrew Jackson.
Trump, meanwhile, has lost the popular vote by considerable margins in both of his races and was only competitive because of the Electoral College. He lost by almost three million votes nationwide to Hillary Clinton in 2016 and by more than seven million votes to Biden four years later.
2024
So can Trump replicate Cleveland’s accomplishment of winning two non-consecutive terms in office? Right now, we appear headed for another nail-biter of an election, absent an event that tips the scales one way or another in the next two months. (Perhaps next week’s presidential debate?) So Trump has a coin flip of a chance to join Cleveland in the history books.
If Trump does win, however, there is a strong likelihood it would be a repeat of his 2016 victory, meaning an electoral win but a popular vote loss. As of today, most polls have Harris ahead in the national popular vote, but the battleground states are somewhere between a toss-up and leaning towards Trump.
Stay tuned.
This essay was written for Substack, but parts of it were adapted from my book, Quest for the Presidency: The Storied and Surprising History of Presidential Campaigns in America (Lincoln, Nebraska: Potomac Books/University of Nebraska Press, 2022).
Again, thank you for providing history that I didn’t previously know. The second candidacies of Van Buren and Fillmore was a revelation.