If the Past Is Prologue: Trump vs. Biden II

Most historians and political pundits are aware of the simmering rivalry between Grover Cleveland and Benjamin Harrison. A native of New Jersey, Cleveland was elected mayor of Buffalo in 1881 and governor of New York State the following year. As governor, he worked closely with state assembly minority leader Theodore Roosevelt to push through anti-corruption legislation, winning him a national reputation for honesty and integrity.

In 1884, Cleveland defeated former Sen. James Blaine of Maine by just 57,577 votes to become the first Democrat elected president since James Buchanan in 1856 and the first Democrat to serve as president since Andrew Johnson left office in 1869. Running for re-election in 1888, Cleveland won the popular vote by more than 90,000 votes but lost the electoral vote 233-168 to Republican Benjamin Harrison.

Four years later, Cleveland and Harrison faced off in a rematch with Cleveland winning the popular vote by more than 380,000 votes and the electoral vote by a margin of 277 to 145, thus becoming the first and only (so far) U.S. president to serve two non-consecutive terms.

Will Donald Trump be the second?

Before answering that question, let’s look at – and learn from – other presidential candidates who ran more than once… some of whom also lost more than once.

Topping the list are Henry Clay and William Jennings Bryan. Clay has the distinction of losing three different times as the standard bearer of three different parties. In 1824, he was one of four men to run as a Democratic-Republican when it was America’s only major political party; in 1832, he was nominated by the National Republican Party; and in 1844, Clay ran on the Whig Party ticket. Bryan was the unsuccessful Democratic nominee in 1896 and 1900, losing both times to Republican William McKinley. After laying low in 1904, Bryan once again secured the Democratic nomination in 1908… and lost once again, this time to William Howard Taft, Teddy Roosevelt’s handpicked successor.

Two-time major party nominees and two-time presidential losers include Thomas Dewey (1944 and 1948); and Adlai Stevenson (1952 and 1956). Dewey lost to Franklin Roosevelt the first time around and to Harry S. Truman the second time, while both of Stevenson’s losses came at the hands of Dwight D. Eisenhower.

Lest Mr. Trump become disheartened however, there are multiple examples of losing presidential candidates coming back to win four years later. Thomas Jefferson was the first to accomplish that feat, losing to John Adams in 1796 before winning their rematch in 1800. Andrew Jackson pulled off a similar comeback in 1832, defeating John Quincy Adams after losing to him four years prior.

In 1836, Democrat Martin Van Buren defeated Whig William Henry Harrison only to see Harrison turn the tables on him four years later. However, winning the rematch was small consolation for Harrison as he died just 32 days after taking office.

The last losing presidential candidate to come back and win a subsequent election was Richard Nixon, who narrowly lost to John F. Kennedy in 1960 before squeaking by Hubert Humphrey in 1968.

And so, if the past is prologue, Donald Trump has about a 50-50 chance of beating Joe Biden this November. It won’t exactly be a Louis-Schmeling or Ali-Frazier type of rematch – or even Rocky Balboa vs. Apollo Creed for that matter – because those boxers were all in their respective primes at the time. However, something tells me that the 2024 presidential election may be bloodier than all those title fights put together because this time, there is far more than a world heavyweight championship belt at stake.