If former President Donald Trump wins the election, he'll be just the second president to reclaim the office after losing his first bid for re-election. Our Bree Driscoll breaks down the historical significance of “If She Wins or If He Wins.” We look at how Trump's attempt to retake the White House is a race for the ages.
What You Need To Know
- Former President Trump would be only the second President to win a second term after losing his first bid for reelection
- Women have been running for President for more than a century
- How will gender shape the presidential election?
The eclectic studio of Artist Scott LoBaido is saturated with patriotic paintings, but the figure most prominently featured is Former President Donald Trump. LoBaido portrays Trump as a superhero, as a survivor and as a pillar of physical strength.
“You can see, he's got he's got some muscles underneath there,” LoBaido said, pointing at one of his paintings. “Because I do feel that at this point in American history, we need strength.”
If Trump is elected this November to lead our country again after suffering defeat in 2020, he will be joining the ranks of only one other man.
“Grover Cleveland and Donald Trump are unique,” said Louis Picone, a history professor at William Paterson University. “They won the presidency and then they lost it. And now they're trying to regain the presidency.”
It was not without others’ lack of trying. Four other presidents attempted to regain the presidency and failed; Martin Van Buren in 1844 and 1848 and Millard Fillmore in 1856.
Picone said the two “weren't incredibly popular presidents anyway.”
But more notable figures tried too. Ulysses S. Grant attempted the feat in 1880, before term limits and four years after serving his second term. Teddy Roosevelt, as well, ran as a third-party candidate in 1912.
But only one, Cleveland, was able to retake the White House after enduring a loss, and did so by charting his own path.
“Grover Cleveland had a meteoric rise in politics. He went from the mayor of Buffalo in 1881 to the president of the United States to winning the presidency in 1884,” Picone explained.
So can former Donald Trump be the second person in history to achieve such an elusive accomplishment? His political rise was also quick, although he had been in the limelight for most of his adult life as a real estate developer and reality TV star.
Trump’s first official steps into the political arena were when he ran for president in 2016 and won. He swayed voters with claims he would “drain the swamp.”
A similar claim was made by Cleveland, a Democrat, who ran as a reformer. But Cleveland’s 1884 campaign faced a sex scandal.
“A woman named Maria Halpin had claimed that Grover Cleveland fathered an illegitimate child with me,” explained Picone.
Trump has also faced his own sex scandals, including alleged affairs and subsequent payoffs of Playboy model Karen MacDougal and adult firm star Stormy Daniels.
Cleveland ended up weathering his storm and took the presidency in 1884.
“Grover Cleveland is known as the veto president. He vetoed more bills than any of his predecessors combined,” Picone said.
When he ran for reelection in 1888 against Republican Benjamin Harrison, he lost.
“Someone asked him, why did you lose, Mr. President? And he said, ‘because Harrison had more votes than I did.' So he believed in democracy. He believed in the vote,” said Picone.
Cleveland’s response stands in stark contrast to Trump, who refused to accept his loss to Joe Biden in 2020.
In 2022, Trump decided to throw his hat back into the ring for a rematch with President Biden; again, with a very different outlook from Cleveland.
“[Cleveland] was happy being out of politics,” Picone said.
Cleveland was enjoying spending his time fishing, but his wife Francis had a different outlook.
On the day they left the White House, in 1888, “she told one of the servants, ‘leave everything exactly how it is’,” Picone said. “‘Because I'll be back four years from today.’”
It was a bold prediction that came true when in 1892, Cleveland won his rematch with Benjamin Harrison. The win cemented him as the only president to serve non-consecutive terms. While Trump was initially looking at a rematch with Joe Biden, he now faces a new opponent in Vice President Kamala Harris.
“I look at Grover Cleveland and I look at Donald Trump and really see them as running two different races,” Picone said. “They're running the race against their opponent, but they're also running the race against the ghost of themselves.”
In Trump’s case, he’s looking for a comeback in a country that loves a comeback story.
“They beat the hell out of this man. They slaughtered this man. Hello, resilience. You know the comeback, the underdog,” Lobaido said. “He didn't have to do this. But he's doing it for a reason.”