One, Twice, Three Times A Maybe: A History of Presidential Losers and Potential Trump Run

With Donald Trump having been acquitted by the Senate, one of the big questions for the next four years is whether he will run again in 2024. There’s no legal restriction on him doing so. He got 74 million votes in the last election and the state GOP orgs are so mindlessly devoted to him, they are censuring Senators and Congressman for being insufficiently groveling. Delusions about the 14th Amendment not withstanding, Congress can’t actually stop him short of another impeachment. So … will he?

I won’t pretend to be able to read the tea leaves when it comes to where the Republican Party goes from here. Nor will I pretend to be able read the leaf pile of Donald Trump’s mind when it comes to whether he will actually do so. But…it might be interesting to look at history on this subject. The last time I did this, I pointed out that it was unprecedented in modern political history to throw out an incumbent president with a good economy. And given how close this election was with a bad economy, I think that review stands up.

Let’s take a look at presidential candidates who ran for office again despite losing a previous election. For the purposes of this exercise, I’ll exclude primaries, since that’s an entirely different can of worms.

John Adams and Thomas Jefferson both “lost” elections and then ran again and won. But the political/legal landscape before 1804 was very different. Parties were fluid to non-existent and the Presidential runner-up became Vice-President. The election of 1800 — aka the nastiest election in American history — ended up in a contest between two members of the same party and was decided by the House. Lin-Manuel Miranda already wrote a thing about that one, so we’ll move along.

Charles Pinckney ran as the Federalist candidate in 1804 and lost to Jefferson in the most lopsided landslide in American history. To be fair, that was probably Hamilton’s fault again, since he got himself killed in a duel that left his party in ruins. Pinckney was nominated again in 1808, probably because the choices for the Federalists were down to him, John Adams and a small poodle named Robert. He was destroyed again, although not as badly as 1804. If Pinckney had made similar progress every four years, maybe he would have become President by 1820.

Andrew Jackson lost the election in 1824 and then won in 1828. But the election of 1824 was a mess. Jackson actually won the popular vote by quite a lot. But because four candidates — all from the Democratic-Republican Party — split the ballot, he only had a plurality, not a majority, of the electoral vote. It went to the House, who elected John Quincy Adams, at least partially because Henry Clay hated Jackson so much. By 1828, however, the Democratic-Republican Party had split in two and we had a race we might recognize today between two major parties. Jackson won easily. Again.

William Henry Harrison lost the election of 1836. But … in words that should now be familiar … the election of 1836 was a mess. For a dozen years, the country had been divided between the Andrew Jackson Party and whatever group of nincompoops constituted the Not Andrew Jackson Party under various monikers. By 1836, the Not Andrew Jackson Party finally had coalesced into the Whigs. Hoping to repeat the “success” of 1824, they ran multiple candidates to divide the electoral vote and throw it to the House. Van Buren won a majority anyway. With the Whigs more organized in 1840 — they literally had their first convention in 1839 — Harrison was the nominee and defeated Van Buren handily. It didn’t do him a lot of good; he died 31 days into his term.

Grover Cleveland is probably the best hope for those who really can’t go without MAGA 2024. By this time, politics had coalesced into a form that would be roughly familiar to us but had very different underpinnings. We had the two parties — Republican and Democrat. The Democrats controlled the South, the Republicans controlled the North and a series of very close presidential elections turned on a few key swing states. In this case, the divide was over the Civil War and its aftermath as opposed to today’s divide which is over … uh … cancel culture?

During this period, the swing states tended to go Republican — the GOP won the vast majority of elections between Appomattox and the Stock Market Crash. But in 1884, the Republican nominee — Blaine — was corrupt and unpopular and Grover Cleveland won a close election. 1888 was equally close but New York and Indiana flipped, giving the election to Benjamin Harrison, who won despite losing the popular vote. Cleveland was the nominee again in 1892 and he flipped a number of states, partially due to a Populist candidate on the ballot, and won a second term.

This is probably the situation that is most comparable to our current one and one that would give the MAGA 2024 die-hards some hope. A divided nation, several elections that turned on key swing states, popular-electoral divides, etc. But Donald Trump is no Grover Cleveland. Cleveland was 47 when he was first elected and 59 when he left office for good. He was a career politician who was respected for his honesty, integrity and leadership. The Democrats were at such an electoral disadvantage that only two Democrats won presidential elections between 1861 and 1933. One was Wilson, who was helped by Roosevelt splitting his own party. Cleveland was the other, winning because he was respected and was probably one of the better Presidents of the late 19th century. Donald Trump is no Grover Cleveland.

Cleveland’s administration ended with a changing Democratic Party that would nominate Williams Jennings Bryan three times in four tries. He never came particularly close to winning but he had a strong impact on the Progressive Era of American politics.

Thomas Dewey was the Republicans’ sacrificial victim in 1944, losing handily to FDR. In 1948, he ran again. He was expected to win, mostly because Strom Thurmond was drawing votes in the South for his segregationist ticket. That proved to be wrong. Truman won anyway.

In 1952, the Democrats nominated Adlai Stevenson, who lost handily to Eisenhower. In 1956, they nominated him again for some reason and he lost again. There’s probably an entire book to be written about the Stevenson thing. He was the first in a long line of Democratic candidates who were popular with liberal elites and then flopped on election night against a supposedly less-intelligent candidate. This was also at a time when the Democrats’ New Deal coalition between racist Northern liberals and racist Southern conservatives was fracturing because the Northern liberals were becoming slightly less racist, a rift that would widen and then completely fracture over the next four decades.

You’ll notice that, up until this point, all the post-Civil War re-nominees have been Democrats. That changed in 1968 when Richard Nixon, having lost a very close election 1960¹ and having supposedly quit politics in 1962, won the nomination and the presidency in 1968. There were (and still are) many Nixon supporters who thought the 1960 election was stolen by Mayor Daley. This is incorrect — Kennedy could have lost Illinois and still won. But resentment over that, over Civil Rights and over 1968’s riots propelled Nixon to victory. This election came up quite frequently this summer when Republicans asserted that the Floyd protests would propel Trump to victory on a similar “law and order” platform. I thought it was odd to run a campaign arguing that you will address the lawlessness and chaos that erupted under…uh…yourself. But such was politics in 2020.

I suppose there are a lot of MAGA 2024 diehards eyeing off of 1968 as well. If so, they shouldn’t. Nixon was only 55 in 1968, far younger than Trump. For all his faults, Nixon was a skilled political operative who had the support of his party. Moreover, Nixon mainly won in 1968 because the Democratic Party split when the slightly more racist Southern Democrats decided they had enough of this Civil Rights business and voted for George Wallace. Had they stayed in the Democratic tent, Nixon would have lost again. Instead, they eventually decided that, with both parties supporting Civil Rights, they might as well go to the more conservative one. Nixon won in a landslide in 1972. And by the 1980s and 1990s, segregation was a dead issue, and the Southern Democrats were in the conservative tent for good.

That’s the history, then. What is the lesson? I’m not sure any lesson can be applied to Donald John Trump, who is the focus of a political cult the likes of which we’ve never really seen and whose philosophy is defined less by patriotism and principle than by whatever he’s thinking in that particular moment. I predicted he would lose in 2016 and I was wrong. I predicted he would win in 2020 and I was wrong. It’s possible we are in the midst of a major re-alignment in American politics right now, but such things are hard to see in the moment and never quite as linear as history books would like you to believe. The Republicans could easily nominate Trump again in 2024. Or go with a Trump-wannabee flyweight like Josh Hawley. Or scuttle back to a sensible candidate like Ben Sasse or something. Or they could split the difference and nominate someone who’s has one foot in the asylum and one foot in the establishment, like Nikki Haley.

Just throwing out some speculation: if he did run, I would expect him to win the nomination. This has happened multiple times in American history. But I would also expect, barring an economic collapse or some other catastrophe, for him to lose the general election. Incumbency is powerful. And the public often tires of ex-presidents and is glad to see the back of them. The only two losers who have successfully run and won were Cleveland and Nixon. Both were younger, smarter, savvier and more-respected than Trump. And both won elections that turned on external factors: a populist third party candidate in 1892 and a summer of chaos in 1968.

In short, it behooves the Democrats to take the possibility of a Trump run seriously. This was the biggest reason I was disappointed that they failed to call witnesses for the impeachment. It wasn’t about persuading Republicans; it was about revealing the culpability and malfeasance of Donald Trump as thoroughly as possible. It was about trying to reduce — however infinitesimally — the possibility that we will have to go through another insurrection in four years.²

The gripping hand, however, is Trump himself. Donald Trump ran in 2016 expecting to lose and start his own PAC/TV network. He loved speaking to crowds and tweeting but hated the business of actually running the government. And while I’m sure, in the recesses of his rancid little brain, he still thinks he won the election, the prospect of starting it up all over again has got to be daunting. I don’t think he’ll actually run. He’ll start a PAC. He’ll roll in the money. He may even start a campaign so that people have excuses to give him even more of their hard-earned cash. But I expect he’ll do just enough to create chaos in the GOP primary. And without a strong personality to oppose him — one that I don’t see in any Republican right now — he will be successful in doing so.

But I’ll bookmark this in case I have to be eating these words in four years. Because you never know in politics. And you never know with someone as reckless, unpredictable and narcissistic as the 45th President.

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1. Arguably winning the popular vote.
2. I also think trying to kneecap a 2024 run was the reason for Mitch’s “My vote for acquittal notwithstanding, Trump was guilty as hell” two-step.