Former President Trump became the Republican Party’s presumptive nominee earlier this month, making him one of only a handful of people to have been a major party’s White House nominee three times.
Here are the five people in U.S. history who previously earned that distinction:
Thomas Jefferson
As political divisions grew throughout George Washington’s presidency, Thomas Jefferson became the leader of the Democratic-Republican Party against the Federalist Party led by John Adams. Both men were their party’s favorites for determining Washington’s successor in the 1796 presidential election, the first contested one in U.S. history.
The electoral system of the day made the person with the most votes the president and the second most votes the vice president, so the parties would each nominate two people for president with the intention that one would become president and one vice president.
The campaign was particularly intense, with Federalists accusing Jefferson of being a Francophile and Jefferson’s supporters accusing Adams of wanting to bring a monarchy to the U.S., according to the University of Virginia’s Miller Center. Adams eked out a win over Jefferson by a 71-68 vote in the Electoral College, but Jefferson became Adams’s vice president as the second-place finisher.
Adams sought reelection in 1800 and was opposed by Democratic-Republican candidates Jefferson and former New York Sen. Aaron Burr. The race was just as — if not more — personal between Adams and Jefferson than four years earlier, but Adams fell short this time and was denied a second term.
But Jefferson and Burr finished with 73 votes each, sending the election to the House to decide. Jefferson was intended to be his party’s choice for president, but Burr refused to back down. Jefferson eventually secured the presidency by winning in the House on the 36th ballot.
Jefferson ran for reelection in 1804 as a popular president and easily won the election over Federalist Charles Pinckney, only losing two states. This time, the Constitution had been amended so a separate vote would be held for vice president, avoiding a repeat of the past two elections’ complications.
Grover Cleveland
Grover Cleveland, the New York governor, was the front-runner for the Democratic nomination in 1884 after gaining a reputation for being honest and effective.
Republicans had dominated presidential elections for more than two decades heading into the 1884 election. But Cleveland had advantages, including an appeal to middle-class voters from both parties, his emphasis on hard work and merit, and his ties to his home state, which had more electoral votes than any other at the time.
He also was facing a weakened opponent in Sen. James Blaine (R-Maine), who angered various factions of his party, according to the Miller Center. Cleveland won by one of the narrowest margins in U.S. history, carrying the state that decided the election — New York — by just more than 1,000 votes.
Cleveland was easily renominated at the Democratic National Convention in 1888, putting him against Republican Benjamin Harrison, a former senator and grandson of President William Henry Harrison.
Tariff policy was a key issue of the race, with Cleveland supporting lower tariffs and Harrison advocating for their increase.
Cleveland won the popular vote but lost the Electoral College, giving the presidency to Harrison.
Cleveland faced some opposition for the Democratic nomination in 1892 but was the front-runner and won on the first ballot, setting up a rematch with Harrison. A third party called the Populist Party that gained the support of farmers nominated James Weaver and won more than 8 percent of the vote, according to the Miller Center.
Backlash to the Harrison administration’s economic policies helped Cleveland become the only person to win two nonconsecutive terms as president.
William Jennings Bryan
A few notable candidates pursued the Democratic nomination in 1896, but former Rep. William Jennings Bryan emerged as the youngest person nominated for president at 36 years old. He gained widespread attention as a fiery speaker denouncing the gold standard and supporting the inclusion of silver in the money supply.
He was also the first candidate to actively travel throughout the country to campaign instead of relying on his supporters, while Republican William McKinley usually addressed supporters from his front porch, according to History.com.
Bryan’s support centered around populists and rural areas, while McKinley, as a proponent of big business, focused on urban centers. McKinley comfortably won with a sweep in the Northeast and some support from Midwestern farmers and industrial workers.
Bryan sought the presidency again four years later and easily won renomination to face McKinley a second time. But he struggled to improve, with McKinley popular from victory in the Spanish-American War and an improving economy. McKinley ended up expanding his margin of victory from his first election.
Bryan chose to sit out the 1904 election but tried a third time in 1908 against William Howard Taft. He again attacked big business and positioned himself as a champion of the common man, vigorously campaigning, but he suffered his worst defeat of all three presidential runs, according to the Library of Congress.
Franklin Roosevelt
The governor of New York, Franklin Roosevelt was one of the top choices for the Democratic nomination in 1932. With President Herbert Hoover deeply unpopular amid the Great Depression, the Democratic candidate would be in a strong position to win.
Over a few ballots, Roosevelt’s supporters were able to win their candidate the necessary delegates to clinch the nomination. What put him over was an agreement to make House Speaker John Nance Garner his running mate in exchange for his support.
Roosevelt went on to handily win the election over Hoover in a landslide. He easily received the 1936 nomination and won in an even larger landslide in 1936.
Despite his popularity, Roosevelt faced some pushback within his own party when he decided to seek a third term in 1940, breaking past precedent. He avoided directly saying whether he was interested in another term for a while, but his political operatives arranged for an effort to draft him as the nominee, according to the Miller Center.
Garner opposed Roosevelt’s nomination and ran himself, but Roosevelt secured it easily. Republicans improved their margin from 1936 in the general election, but Roosevelt still won in a landslide.
Roosevelt’s renomination in 1944 was all but certain with World War II ongoing. He faced his biggest challenge yet from New York Gov. Thomas Dewey, but the country kept with the incumbent to elect him a fourth time.
Richard Nixon
Richard Nixon was a clear choice for the 1960 Republican presidential nomination after having served two terms as Dwight Eisenhower’s vice president. He had an advantage in experience over his Democratic opponent, Massachusetts Sen. John F. Kennedy.
But Kennedy demonstrated himself to be a much more effective campaigner than Nixon. The Civil Rights movement and the Cold War were among the top issues of the race.
Kennedy gained an influential endorsement from Martin Luther King Sr., the father of the Civil Rights leader, just weeks ahead of the election, contributing to an increase in his support among Black voters. He squeaked out a popular-vote win of just more than 100,000 votes on the way to victory, according to Kennedy’s presidential library.
Nixon stayed out of the 1964 race but sought the presidency again in 1968, facing a few primary opponents but outlasting them to win the nomination. He started the general election with a big lead over the Democratic nominee, Vice President Hubert Humphrey, with President Lyndon Johnson’s administration unpopular amid the Vietnam War, according to the Miller Center.
The margin tightened significantly before Election Day, but Nixon managed to win, though with less than a majority of the vote.
Nixon faced nominal opposition to the GOP nomination in 1972, and he didn’t have a much larger obstacle to winning reelection. He faced Democratic South Dakota Sen. George McGovern, who struggled to run an effective campaign, notably replacing his running mate soon after the convention.
Nixon led in the polls by a large margin and never let it up, coasting to a landslide.