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A historical president to inspire Donald Trump

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Barack Obama and Bill Clinton are rallying behind President Joe Biden in his reelection campaign. Plans for what Obama apparently views as an “all-hands-on-deck” effort to stop former President Donald Trump speak to the threat Trump represents to these former Democratic presidents.

Trump, on the other hand, does not have a stable of Republican predecessors in his corner. Former President George W. Bush, no Trump fan, is the only other living Republican who sat in the Oval Office.

Perhaps Trump will look to history for inspiration. He likes to try to compare himself to Abraham Lincoln, for instance. But there is a better example.

Grover Cleveland, while a Democrat, is the only other man who won the White House, lost the White House and then was nominated again by his party for a third straight time.

Trump and Cleveland are in some ways inverse characters. While Trump won the White House while losing the popular vote in 2016, Cleveland lost the White House while winning the popular vote in 1888.

Cleveland ultimately served as both the 22nd and 24th US president. Like Trump, he survived scandal on his way to the White House. But the men are extremely different, as I found when I talked to Troy Senik, author of “A Man of Iron: The Turbulent Life and Improbable Presidency of Grover Cleveland.” Senik is also a former speechwriter for Bush and today runs the digital media company Kite & Key.

Our conversation, conducted by email, is below.

What ties Trump and Cleveland?

WOLF: Trump and Cleveland are the only two US presidents to be nominated by their party after defeat. Are they alike in any other ways?

SENIK: Trump and Cleveland have vastly more differences than similarities, but there are a few areas of overlap. Some of them are superficial – both New Yorkers, both amongst our heaviest presidents – but some of them are more substantive.

Trump and Cleveland were both political outsiders. While Cleveland had held elected office prior to going to the White House, he had a rapid ascent, going from mayor of Buffalo to president of the United States in just three years.

Cleveland shared Trump’s distaste for the press, annoyed by their intrusions into his private life and irritated by the fact that the openly partisan media of the late 19th century would sometimes completely fabricate stories.

Cleveland also ran for office on his own version of “drain the swamp,” though it was a lot more understated than Trump’s. He was primarily concerned with reforming the civil service so that more federal employees would be hired on the basis of merit rather than because of their political connections.

Trump’s out for revenge. Why did Cleveland run again?

WOLF: Trump says he is running this time for “retribution.” Why did Cleveland run again?

SENIK: Unlike Donald Trump, Grover Cleveland did not leave office planning for a comeback. He was relieved to be out of the White House and showed little interest in making another run after 1888.

This illustration from 1888 shows the St. Louis Convention Hall during a speech renominating Grover Cleveland. - Library of Congress
This illustration from 1888 shows the St. Louis Convention Hall during a speech renominating Grover Cleveland. - Library of Congress

What eventually motivated Cleveland to run a third time was a split within the Democratic Party, where a new wave of populist Democrats were threatening to take over the party and steer it away from Cleveland’s conservative, limited-government approach. He ran primarily in order to prevent the populists from taking over the party.

Could Cleveland have been a successful politician today?

WOLF: Cleveland was successful in the era of party delegates picking presidential candidates. Could he have been a successful candidate today, when it’s primary voters?

SENIK: The answer to this question is probably both “yes” and “no.” The Grover Cleveland of the first term could plausibly succeed in today’s environment because he was scratching a real itch for the electorate. The politics of the day were seen as overwhelmingly corrupt, and Cleveland won on the basis of his reputation for integrity and the idea that he couldn’t be bought.

The Grover Cleveland of the second term, however, won over Democratic elites much more than he won over the rank and file. At a time of growing populism within the Democratic Party, he was chosen as the nominee because he was not willing to go to the same lengths as the populists, who wanted much greater government intervention in the economy.

This would be something like today’s more populist Republican Party getting Mitt Romney as its nominee.

Are they polar opposites?

WOLF: Trump won his first election but lost the popular vote. Cleveland lost his second election, but won the popular vote. Trump imposed tariffs. Cleveland reduced tariffs. Are they polar opposites?

SENIK: They are very different men.

Trump is a populist; Cleveland regarded populism as preying on the worst instincts of the American people.

Trump has expansive notions of presidential power; Cleveland thought one of his foremost responsibilities as president was to respect the boundaries placed on the office by the Constitution.

Trump is theatrical; Cleveland regarded that kind of behavior as vulgar and beneath the dignity of the presidency.

Trump supports higher tariffs; Cleveland spent most of his two terms fighting to lower them.

Trump has a hard line on immigration; one of Cleveland’s final acts as president was to veto a bill prohibiting immigration by the illiterate.

In terms of ideology, temperament and conduct in office, it’s hard to think of two presidents more different than Donald Trump and Grover Cleveland.

Cleveland successfully survived major scandal

WOLF: Cleveland admitted to an affair that produced a child with a woman who was later committed to an asylum, and he ultimately married a woman who had been his ward – any of which seems like it would hurt a candidate’s prospects today. How was scandal viewed differently back then?

SENIK: The first thing to know is that the popular tellings of both of these stories tend to overstate the facts as we know them.

About a decade before he ran for president, Cleveland did indeed have a relationship with a woman who ended up having a child. We don’t know for certain whether the child was his – and there’s at least some suggestion in the historical record that he wasn’t sure either – but it seems more likely than not. Cleveland never issued either a public acknowledgement or denial of paternity.

The relationship was not an “affair” in the traditional sense – neither of them were married at the time – and many of the other details are also often distorted (the “asylum,” for example was more of a sanitarium, where the woman in question, Maria Halpin, was being treated for alcoholism).

This was a significant scandal during the 1884 presidential election, but Cleveland weathered it successfully for two reasons.

(1) The original press reports were so grossly exaggerated that by the time more of the details came out, the public was more relieved that Cleveland (whose political standing was largely based on his reputation for good character) wasn’t incorrigibly evil than they were outraged by the fact that he wasn’t quite as spotless as they had once believed.

(2) Cleveland chose to take the criticism that came with the scandal rather than trying to endlessly litigate the particulars of it, which ended up sealing his reputation as someone who’d take tough stances rather than try to wiggle out of uncomfortable situations.

As for Cleveland’s marriage to a much younger woman, the understanding of that has also been somewhat distorted over the years.

President Grover Cleveland marries Frances Folsom Cleveland on June 2, 1886, in the Blue Room at the White House. - Thure De Thulstrup/Library of Congress
President Grover Cleveland marries Frances Folsom Cleveland on June 2, 1886, in the Blue Room at the White House. - Thure De Thulstrup/Library of Congress

Cleveland’s wife, Frances, was his “ward” only insofar as Cleveland had what was essentially power-of-attorney for her family (her deceased father was Cleveland’s former law partner). He did not raise her (in fact, she lived in another state for part of her childhood) and the romantic relationship didn’t begin until she was in college, before which Cleveland had secured the blessing of Frances’ mother.

Far from being a scandal, Cleveland’s marriage (which occurred while he was president) captivated the nation, and Frances Cleveland became probably the most popular first lady until Jacqueline Kennedy.

Was Cleveland a good president?

WOLF: You may be biased since you wrote a biography about the guy, but was Cleveland a good president? Was he better than Trump or Biden?

SENIK: I will forego passing judgment on either Presidents Trump or Biden, because one thing being a presidential historian teaches you is that you often need decades to pass before you can come to a sober conclusion about a president’s legacy.

As for Cleveland, the best thing you can say about him is that he was one of the most principled, incorruptible men to ever hold the office and that he consistently did what he thought was in the country’s best interest rather than what was to his political advantage.

The worst thing you can say about him is that this same sense of principle also made him stubborn and inflexible, and he suffered a lot of (probably unnecessary) political defeats because he wasn’t willing to make the kind of concessions that tend to lubricate political life.

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