Trump has to overcome the long arc of history if he is to win re-election

The former president has never been short of confidence, but he faces major challenges if he is going to return to the White House, writes Andrew Buncombe

(Getty/iStock/AP)

Several have tried – among them Herbert Hoover – but only one succeeded.

So if Donald Trump is to win the presidency once more after having suffered defeat to Joe Biden in 2020, he will be in very singular company indeed – that of Grover Cleveland.

Cleveland, who served as the 22nd and 24th president of the US, is the only person to have successfully won two non-consecutive terms. Can Trump become the second?

“Now, Jerry, I want you to take good care of all the furniture and ornaments in the house, for I want to find everything just as it is now, when we come back again,” Cleveland’s wife, Frances Cleveland, the youngest ever first lady, told a member of the White House staff after her husband failed in his first attempt at re-election in 1888.

True enough, four years later, Cleveland defeated incumbent Republican Benjamin Harrison, and he and his wife were back in the White House, rearranging the furniture to their own liking.

Some have drawn comparisons between Cleveland and Trump, not least for a sense of secrecy over their personal affairs. Cleveland was particularly secretive about his medical history, largely because he suffered from cancer of the mouth, which required surgery, and feared that revealing the nature of his illness would worsen public anxiety over the economic depression.

Yet, other than having to work against the backdrop of inflation and economic depression, there are more differences than similarities. For a start, Cleveland was a Democrat, and Trump is a Republican, though of a variety that would have been unrecognisable even a few years ago.

Cleveland was the 22nd and 24th president of the US (AP)

Cleveland was 47 when he was elected to office the first time, and 55 the second. Trump was 70 when he beat Hillary Clinton back in 2016, and will be 78 by January 2025, when a theoretical second term would begin. The only person older than that to have served in the role is Joe Biden.

There are other stark differences as well. Cleveland won the popular vote in three election contests, though in 1888 he lost the electoral college 233-168, and thus the presidency, to Harrison. Trump has already lost the popular vote twice, but won an electoral college victory in 2016, even though Clinton gathered around 3 million more votes than he did.

And politically and temperamentally, the pair do not have much in common.

“While there are a few superficial similarities between Grover Cleveland and Donald Trump, their paths back to the White House couldn’t be less similar,” Troy Senik, a former presidential speechwriter and author of a forthcoming biography of Cleveland, tells The Independent.

“Cleveland was fighting a growing populist insurgency within his own party, while Trump is leading one. Indeed, Cleveland’s task was in some ways harder than Trump’s: the best way to understand the improbability of his victory in 1892 is that it would be something like today’s Republican Party nominating Mitt Romney.”

Cleveland, the first Democrat elected after the civil war, was born in New Jersey in 1837 and raised in upstate New York. His official biography on the White House website notes that he was one of nine children of a Presbyterian minister.

“As a lawyer in Buffalo, he became notable for his single-minded concentration upon whatever task faced him,” it says. “At 44, he emerged into a political prominence that carried him to the White House in three years. Running as a reformer, he was elected mayor of Buffalo in 1881, and later, governor of New York.”

When he entered the White House in 1885, he was a single man, and complained about the luxuries of his official residence. “I must go to dinner, but I wish it was to eat a pickled herring, a Swiss cheese and a chop at Louis’ instead of the French stuff I shall find,” he wrote to a friend.

In the summer of 1886, Cleveland married 21-year-old Frances Folsom. The pair were wed in the Blue Room at the White House, and he was the only president to marry while in office.

Author and historian Matthew Algeo has written several books about US presidents, including one with a very long title – The President Is a Sick Man: Wherein the Supposedly Virtuous Grover Cleveland Survives a Secret Surgery at Sea and Vilifies the Courageous Newspaperman Who Dared Expose the Truth.

Algeo admits he is very much a fan of Cleveland, who he says was one of the nation’s least well-known and most underappreciated commanders-in-chief.

He says he brought a sense of calm and practicality to the job, and when he was elected for a second time in 1892, he was clearly on a roll, given it was his third victory in the popular vote.

“When you look at Cleveland coming back to reclaim the office in 1892, he was sort of on a streak. He clearly had the support of a lot of Americans, and the majority of Americans who had voted in the past two elections,” says Algeo, whose other books have included an account of Harry Truman. “So he was really coming at it at a different angle to [that from which] Trump would be coming at it.”

He adds: “I think Trump will run a campaign of grievances. And Grover Cleveland did not do that. He didn’t run a campaign of grievances at all. In fact, the 1892 campaign was one of the most calm in American history.”

Algeo says Cleveland had a decent relationship with the incumbent, Harrison. Weeks before the election, Harrison’s wife became very ill and died. Neither candidate engaged in very much more campaigning after that.

Of course, Trump will not just be trying to go against the historical record. As he seeks a second term, he faces a series of challenges that are very much about events right now, not those at the end of the 19th century.

Firstly, it is very unlikely he will be the only Republican candidate throwing his hat into the ring. People such as former Maryland governor Larry Hogan are already sounding out the field, and engaging in such long-tested requirements as visiting the Iowa state fair.

Mike Pence has been making a series of speeches, seeking to set out a conservative case for himself, and he too has been very visible.

Nikki Haley is expected to be among those seeking Republican nomination in 2024 (AP)

Former secretary of state Mike Pompeo has been speaking at events such as the Family Leadership Summit, while Texas governor Greg Abbott appears very interested in a run.

Then there are the Republicans who challenged in 2016 and failed, but very clearly would be up for another try – senators Ted Cruz and Marco Rubio, along with fresh faces such as Tom Cotton.

Most worrying for Trump would be a challenge from newly re-elected Florida governor Ron DeSantis, who has perfected the art of combining an appeal to people’s sense of anger and anti-establishment sentiment with a younger, fresher face, and who does want to relitigate the 2020 election – something Trump is obsessed with.

Polls suggest that Trump is the preferred presidential candidate of around 50 per cent of Republicans, and that his support is slipping, partly as the noise from the January 6 hearings starts to stick to him, and partly because there are alternative candidates who make a point of seeking to appeal to the former president’s base.

But he retains a very high approval rating within the party and its supporters – perhaps as high as 90 per cent, according to some polls. He would also be helped by a large primary field, as he was in 2016, when opposition against him was diluted.

There are other issues that Trump will have to contend with, not least a succession of investigations of which he is the target, which could potentially end in criminal charges. In addition to the probe by the House committee looking into January 6, he is the subject of an FBI and Department of Justice investigation into materials he took from the White House to his estate in Florida – something that blew up when FBI agents raided his Mar-a-Lago property in the summer and took away a dozen boxes.

Trump is also being investigated in New York, in a civil inquiry led by New York attorney general Letitia James, which seeks to determine whether he fraudulently inflated the value of his assets. When the former president finally appeared in front of James’s officials, he pleaded the fifth amendment more than 400 times as he refused to answer questions.

His New York golf club is also at the centre of an investigation, and Georgia’s Fulton County district attorney Fani Willis is investigating attempts to overturn the former president’s election loss in the state, after he pressured Georgia secretary of state Brad Raffensperger to “find” 11,000 votes in order to change the outcome.

Trump has denounced all of these processes as political witch-hunts, but experts have said it would be astonishing if events such as the FBI raid were not signed off on, both by a judge and by attorney general Merrick Garland. The idea of a former president being charged with a crime feels astonishing, but these are turbulent, uncertain times.

Experts say that, despite all of this, Trump is embarking on his campaign as the favourite.

“No question Trump starts as the frontrunner. His continuing pull on the Republican Party has been obvious through this year’s primaries. His endorsement really matters with the GOP base. Even DeSantis starts far behind,” says Larry Sabato, professor of politics at the University of Virginia.

“Two other obstacles: age and law enforcement. Trump – and Biden – are much older than any other president save Reagan. The same rules of ageing apply to them as to everyone else. Let’s see what Trump’s health is like in a year. And no former president has ever had so many investigations ongoing. It’s a drain on his time and energy, even if he dodge[s] convictions.”

Algeo, the author of the book on Grover Cleveland, also says it would be far from easy for Trump to become president a second time, as history proves. “[For] Trump, I think the election will be very heated, very contested, could get violent at times. And this was not the case in 1892. It was a fairly sedate election,” he says.

Six presidents have sought to win re-election after leaving office, but “Grover is the only president who lost the White House and came back and won it back, and I mean, that’s in itself a remarkable achievement,” adds Algeo. “It gives you an idea of how very difficult it is to do that.”