Ronald L. Feinman is the author of Assassinations, Threats, and the American Presidency (Rowman Littlefield Publishers, 2015, Paperback Edition 2017).

As the presidential campaign of 2024 becomes the center of public attention, former president Donald Trump seems far ahead in the battle for the Republican presidential nomination; if he does win, Trump will join a select group of presidential nominees who have been on the ballot three or more times.

All by himself as the only four-time candidate is Franklin D. Roosevelt, who was the nominee of his Democratic Party in 1932, 1936, 1940, and 1944.  After World War II, the move for a constitutional amendment to limit presidential longevity in office to two elected terms (or a total of ten years if succeeding to the office) was accomplished with the 22nd Amendment, which took effect beginning with the presidency of Dwight D. Eisenhower. FDR also had the unique distinction of being on the presidential ballot as a vice presidential running mate in the failed presidential campaign of Democrat James Cox in 1920.

Two three-time presidential nominees failed to be elected despite multiple attempts.  Henry Clay was on the ballot in the presidential elections of 1824, 1832 and 1844, and was a contender in 1840 and 1848. The winning Whig candidates in those years (William Henry Harrison and Zachary Taylor) died early in their terms of office. William Jennings Bryan was the nominee of the Democratic Party in 1896, 1900, and 1908 and was bandied about as a possible nominee in 1912, before he threw his support to Woodrow Wilson, who went on to win two terms in the White House.

Thomas Jefferson and Andrew Jackson both lost their first bids for the presidency in 1796 and 1824. In times of constitutional crisis and division, they were defeated respectively by the father and son John Adams and John Quincy Adams. Jefferson and Jackson would defeat their Adams nemeses in the next elections, and each served two terms in the presidency. 

Martin Van Buren, Jackson’s second-term vice president would be the last vice president to succeed to the presidency by election (1836) until 1988, when George H. W. Bush succeeded Ronald Reagan. But Van Buren lost the election in 1840, and then ran as the candidate of the Free Soil Party in 1848, winning ten percent of the national popular vote.  If one counts his being on the ballot with Jackson in 1832, Van Buren was on the ballot more often than anyone except FDR.

Grover Cleveland was on the ballot three times, winning the popular vote all three times (1884, 1888, 1892), but losing the Electoral College in 1888 to Benjamin Harrison (whom he then defeated in 1892).  If Donald Trump ends up as the Republican nominee against Joe Biden, this would be the first such scenario of a rematch since 1892.

The final example of a three-time nominee was Richard Nixon, who lost to John F. Kennedy in 1960, but came back as the successful Republican nominee in 1968 and 1972.  He joined only Thomas Jefferson and Andrew Jackson as candidates who had lost, and then came back to win two terms as president.

So Donald Trump might join a short list of third time nominees, but he also has a unique situation as the only president to have lost the national popular vote twice (although he was elected president in 2016).  He would join only Thomas Jefferson (before the era of popular vote being a factor in elections), and Henry Clay and William Jennings Bryan (three time losers) in being on the ballot three times.