Grover Cleveland has been noted for his reformist agenda and opposition to tariffs that presaged the free-trade movement of the 1890s. But the 22nd and 24th president of the United States is perhaps best known for winning two non-consecutive terms in the White House—a feat only Donald Trump has matched with his win in the 2024 presidential election.

In 1884, Cleveland, a Democrat, overcame a sex scandal to defeat Republican nominee James Blaine in a narrow victory. Cleveland admitted that he may have fathered a child with Maria Halpin out of wedlock in 1874, but claimed it “certainly shouldn’t preclude him from serving as president.” Halpin’s story differed greatly, stating the affair was non-consensual. Further, Halpin was “admitted under murky circumstances” to a local asylum for the insane.

Still, with Blaine, a senator from Maine, facing allegations of exchanging political favors for cash, Cleveland was able to secure the presidency.

Four years later, Cleveland lost his 1888 reelection race to Republican challenger Benjamin Harrison despite securing the popular vote. But, in an 1892 rematch, Cleveland defeated Harrison to reclaim the office.

Cleveland’s failed 1888 reelection campaign against Harrison, grandson of former President William Henry Harrison, focused on economic policy issues, including tariffs, but lacked effective management and unity within his party.

The campaign was incompetently run on nearly every front, according to Troy Senik, presidential historian, former presidential speechwriter and author of A Man of Iron: The Turbulent Life and Improbable Presidency of Grover Cleveland.

“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 says.

Still, he adds, the race was close. Cleveland won the popular vote 48.6 percent to 47.9 percent, but Harrison claimed victory with a wide Electoral College margin of 233 to 168.

Cleveland’s defeat was primarily attributable to the narrow loss of two states he'd won in 1884: Harrison’s home state of Indiana and his own home state of New York, “where he had a long combative relationship with the state’s Democratic establishment,” according to Senik.

“It’s worth noting, however, that Cleveland’s margin of victory over Harrison in the popular vote was actually larger than his margin over James G. Blaine in his successful first bid for the presidency in 1884,” he adds.

According to Barbara Perry, co-chair of the University of Virginia Miller Center’s Presidential Oral History Program, Cleveland’s veto of increased benefits for Civil War veterans—and the fact that Harrison served as a general in that war—worked against the incumbent president. Further, Cleveland opposed increased tariffs and lost the support of manufacturers, she adds.

“He was not sympathetic to workers’ rights,” Perry says. “The latter two issues caused him to lose his home state of New York, as Gore lost Tennessee in 2000. Had each man won his home state, Cleveland would have won the Electoral College vote.”

The 1892 presidential election was a rematch, with Harrison and Cleveland serving once again as their party nominees.

“Mrs. Cleveland had told the White House staff upon departing in 1889 to take care of the furniture because she and her husband would be back in four years,” Perry says. “Her husband enjoyed private life but continued to oppose the Republicans’ tariffs and monetary policy. He began to speak about disquiet in the country, especially over how GOP tariffs raised the cost of living. Democrats happily turned to the former president for the 1892 presidential nomination.”

Cleveland did not leave office anticipating another presidential run, Senik adds.

“He was satisfied with his first-term record and was enthusiastic about the idea of a retirement with his wife, whom he had married during the first term,” he says.

Perry agrees, noting that Cleveland vowed not to spar for the nomination. “Instead, he wanted his party allies to bring it to him, and he succeeded,” she says. “Remember, 1892 was 20 years before the first primaries occurred.”

What eventually brought Cleveland back into the fray, Senik says, was a deep dissatisfaction with the populist drift of the Democratic Party, as well as “a concern that the likely alternative nominee—his successor as New York governor, David B. Hill—would draw the party towards the kind of cronyism that he had fought so hard against.”

Senik says the most important thing to understand about Cleveland’s third nomination in 1892 is that it happened before the advent of the modern primary system.

“Had Cleveland had to navigate the Democratic electorate, it’s hard to imagine a scenario in which he would’ve been re-nominated,” he says.

With the economy taking center stage during the campaign and a third-party bid from the newly formed Populist Party, Cleveland again claimed victory in 1892, winning the popular vote 46 percent to 43 percent over Harrison. Populist Party candidate James B. Weaver took five states, but Cleveland sailed to a decisive Electoral College win with 277 votes, compared to 145 for Harrison and 22 for Weaver.

Senik says Cleveland won largely because he had been proved prescient on the tariff issue.

“Republicans had enacted significant tariff increases during the Harrison administration, the costs were felt by voters, and Cleveland’s previously quixotic support of tariff reductions found a new purchase,” he says. “Harrison himself attributed his loss to the fact that ‘The working man declined to walk under the protective umbrella because it sheltered his employer also. He has smashed it for the fun of seeing silk stockings take rain.’”

Cleveland and Donald Trump are the only U.S. presidents to win non-consecutive terms, but others have attempted the feat. Martin Van Buren, president from 1837-1841, ran again unsuccessfully in 1848 under the third-party Free Soil ticket after a platform dispute with the Democratic Party. Millard Fillmore, president from 1850-1853, ran in 1856 as nominee for the Know Nothing Party after the Whig Party collapsed, losing to Democrat James Buchanan.

“Van Buren and Fillmore were on the scene during the political churn that would lead to Civil War,” Perry says. “These conflicts produced a number of one-term presidents.”

Theodore Roosevelt, president from 1901-1909, ran for a third term in 1912 under the third-party Progressive Bull Moose Party when he lost to William Howard Taft as the Republican nominee.

Ironically, Senik says, Cleveland likely succeeded at a comeback where so many other politicians failed “because he wasn’t much of a politician.”

“Woodrow Wilson once wrote of Cleveland that ‘his courses of action were incalculable to the mere politician, simply because they were not based on calculation.’ Cleveland was never especially beloved, but he was respected," Senik says, "and that was precisely because the public knew that he’d do what he thought was right rather than what he thought was politically expedient."