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How Donald Trump hopes to follow in the footsteps of Grover Cleveland

After months of flirting with the idea, former President Donald Trump announced his third bid for the White House – and in doing so, the 76-year-old an incredibly small group of former presidents who returned to the campaign trail even after losing a re-election. 

Needless to say, the move was unusual… however it is not entirely unprecedented.  

In the pantheon of 46 American presidents, four have attempted a political comeback after a failed re-election — however only one has succeeded: Grover Cleveland. 

Cleveland ascended to the presidency in 1884, as the first Democrat to win the seat since 1856, ending his party’s long exile from the White House. He lost reelection in 1888 to Benjamin Harrison, but won again in 1892; thus becoming the 22nd and 24th president. 

If Trump succeeds where so many others have failed, he will be the 45th and 47th presidents, however he will have achieved a feat that is perhaps equal to securing the White House: becoming only the second former president to achieve re-election after a failed campaign. 

The notion has caused historians and pundits alike to comment on the similarities between the two outsize men: both native New Yorkers who started out as political outsiders and nearly had their ambitions derailed by what many believed to be a disqualifying sex scandals.

After months of flirting with the idea, former President Donald Trump announced his third bid for the White House in an hour-long speech on Tuesday night from his Mar-a-Lago resort. Where so many have failed, Trump hopes to follow in the footsteps of Grover Cleveland, the only US president to serve two non-consecutive terms

Cleveland ascended to the presidency in 1884, as the first Democrat to win the seat since 1856, ending his party's long exile from the White House. He lost reelection in 1888 to Benjamin Harrison, but won again in 1892 - thus becoming the 22nd and 24th presidents

Trump announced his bid for the 2024 presidential election, becoming only one of five former presidents hoping to stage a political comeback after a loss

Grover Cleveland was the first president to successfully stage a political comeback after a loss, becoming the 22nd and 24th presidents. The notion has caused historians and pundits to comment on the similarities between the two former presidents: both native New Yorkers who started out as political outsiders and nearly had their ambitions derailed by what many believed were disqualifying sex scandals

Two campaigns marred by sex scandals and a common interest in ‘draining the swamp’

A former mayor of Buffalo and Governor of New York, Grover Cleveland was the first Democrat to be elected after the Civil War. 

Though he was hardly an exciting candidate, he proved to be a solid (if sapless) chief executive. 

Cleveland rose through the ranks on a campaign that promised ‘civil service reform’ which emphasized a smaller and more efficient government that relies on self-sufficiency and individual responsibility. 

Cleveland rose through the ranks on a campaign that promised 'civil service reform' which emphasized a smaller and more efficient government that relies on self-sufficiency and individual responsibility. Similarly, Trump's 2016 signature campaign promise was to 'drain the swamp'

Cleveland rose through the ranks on a campaign that promised ‘civil service reform’ which emphasized a smaller and more efficient government that relies on self-sufficiency and individual responsibility. Similarly, Trump’s 2016 signature campaign promise was to ‘drain the swamp’ 

For the most part, he succeeded in fulfilling his promise by reducing the number of federal employees in departments that he felt had become bloated with redundancy. 

To his own demise and popularity among constituents, he vigorously pursued a policy that barred special favors to any specific groups. 

When drought blighted cattle farmers in Texas, Cleveland vetoed a bill that would appropriate $10,000 to distribute seed grain among the stricken field hands. He wrote: ‘Federal aid in such cases encourages the expectation of paternal care on the part of the Government and weakens the sturdiness of our national character.’ 

He cracked down on railroads that failed to extend their lines according to government agreements, creating the Interstate Commerce Commission as an oversight committee to regulate the industry.

Cleveland also appealed to middle-class voters of both parties as someone who would fight double-dealing in Washington DC and big-money interests. While his Republican opponent in the 1884 election, James G. Blaine (also known as ‘Slippery Jim’), was largely thought of as a puppet of Wall Street and the powerful railroads. 

Similarly, Trump ran on his signature promise to ‘drain the swamp’ in a pledge to uproot political corruption and install a government that served ordinary Americans, not special interests. 

In 2016, Trump nicknamed his opponent, ‘crooked Hillary [Clinton]’ and accused  her of benefitting from a rigged system that rewards the well-connected – as lobbyists move between the public and private sectors. 

In the three weeks before the 2016 election, Trump tweeted ‘Drain the swamp’ 79 times, but critics of his administration said he did very little to actually deliver on the promise. 

In a five-point list of proposals he unveiled to tighten rules for lobbying in Washington, only one was fully implemented. (Later during his 2020 reelection bid, Trump was accused of ‘pay-to-play’ politics when he hosted a $100,000-per-ticket event at his hotel for lobbyists, donors and corporate executives to take turns pitching him their pet issues).

Both men took strong positions on immigration. Trump proposed expanding the wall at the Mexican, and bridled legal immigration to the US by imposing a travel ban from Muslim countries: Iran, Iraq, Libya, Somalia, Sudan, Syria, and Yemen. 

Comparably, Cleveland renewed the Chinese Exclusion Act that declared Chinese immigrants ineligible for naturalization. Though he vetoed a bill that would have required US immigrants to pass a literacy test, Cleveland felt the cultural differences between America and China would be ‘impossible to assimilate’ and posed a danger  ‘to our peace and welfare.’

Halfway through the 1884 race, Cleveland's campaign was plagued by a sex scandal when the press discovered that he fathered an illegitimate child out of wedlock. The mother was a widow named Maria Halpin who implied that their relationship was non-consensual in a sworn affidavit. Above was a popular political cartoon run by Cleveland's political opponents at the time. But when the Democrat won the election by a slim margin of 1,200 votes, the chant of 'Ma, ma, where’s my Pa?' was smugly answered with 'Gone to the White House, ha ha ha!'

Halfway through the 1884 race, Cleveland’s campaign was plagued by a sex scandal when the press discovered that he fathered an illegitimate child out of wedlock. The mother was a widow named Maria Halpin who implied that their relationship was non-consensual in a sworn affidavit. Above was a popular political cartoon run by Cleveland’s political opponents at the time. But when the Democrat won the election by a slim margin of 1,200 votes, the chant of ‘Ma, ma, where’s my Pa?’ was smugly answered with ‘Gone to the White House, ha ha ha!’

Trump's 2016 campaign was also blighted by various sex scandals. Most notably, his relationship wit to the disgraced financier and infamous pedophile, Jeffrey Epstein

Trump’s 2016 campaign was also blighted by various sex scandals. Most notably, his relationship wit to the disgraced financier and infamous pedophile, Jeffrey Epstein

During the 2016 election, Trump was accused of sexual misconduct by 24 women including E. Jean Carroll (pictured) who alleged that he raped her in the dressing room of a department store in the 1990s

 During the 2016 election, Trump was accused of sexual misconduct by 24 women including E. Jean Carroll (pictured) who alleged that he raped her in the dressing room of a department store in the 1990s

Both campaigns were beset by salacious sex scandals halfway through the race. Trump was accused of sexual misconduct by 24 women, one of them, named E. Jean Carroll alleged that he raped her in the dressing room of a department store. 

Also during that time, was the infamous hot mic moment in a former interview with Billy Bush where the president confessed: ‘I’m automatically attracted to beautiful women — I just start kissing them, it’s like a magnet. Just kiss. I don’t even wait. And when you’re a star, they let you do it. You can do anything. Grab ’em by the p***y.’ 

For Cleveland, it was revealed that he had an affair with a young widow named Maria Halpin and fathered a child out of wedlock during his bachelor days.

A popular political cartoon of the time poked fun at the situation, depicting Cleveland with a woman carrying a baby that said ‘Ma, Ma, Where’s my Pa.’

The story broke to national outrage. One piece in the Chicago Tribune asked: ‘It seems to me that a leading question ought to be: do the American people want a common libertine for their president?’ 

Cleveland did his best to get ahead of the scandal. He claimed paternity but painted Halpin as a ‘loose’ woman who was free with her affections to many of his married friends – and that he was merely aiding her by putting their son in a foster family and having her spirited away to a mental asylum. 

In reality, Cleveland’s involvement was much more nefarious. Halpin claimed that the politician relentlessly pursued her. In a sworn affidavit, she implied that his entry into her bedroom was not consensual and alleged that he ‘was forceful and violent.’

After the baby was born, Cleveland had Halpin committed to a mental institution under murky circumstances, only to be released two days later when doctors discovered she was of sound mind. 

Trump lost the popular vote in 2016 by 2.1 percent, but clinched his victory through the electoral college in key battleground states: North Carolina, Florida, Wisconsin, Pennsylvania, and Michigan. 

Similarly, Cleveland won the popular vote in 1892, but only by a narrow margin of .30 percent. Like today, his win was owed to the tight electoral map, which hinged on swing states.

‘For Trump, that’s an important lesson. If re-nominated, he could very well win,’ said Joshua Zeitz, for Politico. 

How Trump and Cleveland both dodged war drafts and shared in their predilection for young women

On a surface level, the two men share a lot of common traits. 

Like Trump who dodged the Vietnam War on account of a timely bone-spurs diagnoses – Cleveland also avoided military service during the Civil War by hiring a substitute to join the Union Army. (A legal practice at the time). He then managed to elude polarizing political battles at the time over Reconstruction, and glide his way into the Oval Office office during the 1884 election. 

During his 2016 campaign, a video resurfaced of Trump comparing his sex life in the 1970s, (and the fact that he avoided contracting any STDs), as his ‘personal Vietnam.’   

‘I’ve been so lucky in terms of that whole world,’ he told Howard Stern in 1997. ‘It is a dangerous world out there. It’s scary, like Vietnam. Sort of like the Vietnam-era.’

‘It is my personal Vietnam. I feel like a great and very brave soldier.’

Other commonalities between Cleveland and Trump, are that both share a predilection for young women. 

Thrice-married Donald Trump has made his weakness for young beautiful women well known. He once owned the Miss America pageant and referred to the fact that he was able to dodge STDs during his wild bachelor days as his own 'personal Vietnam.' Above he is pictured with his wife, former model Melania Trump, and his four eldest children

Thrice-married Donald Trump has made his weakness for young beautiful women well known. He once owned the Miss America pageant and referred to the fact that he was able to dodge STDs during his wild bachelor days as his own ‘personal Vietnam.’ Above he is pictured with his wife, former model Melania Trump, and his four eldest children 

Grover Cleveland is the only sitting president to be married during his presidential term when he wed 21-year-old Frances Folsom at age 49. Cleveland first met Folsom when she was just an infant, as he was a friend of her father's. Later when her father died in 1875, Grover became her unofficial guardian. She is the youngest First Lady in American history

Grover Cleveland is the only sitting president to be married during his presidential term when he wed 21-year-old Frances Folsom at age 49. Cleveland first met Folsom when she was just an infant, as he was a friend of her father’s. Later when her father died in 1875, Grover became her unofficial guardian. She is the youngest First Lady in American history

Donald's third wide, Melania Trump flirted with the idea of becoming First Lady again in a 2021 interview with Fox News where she was asked if she could see herself back in the White House. She replied: 'Never say never'

On Grover Cleveland's final day in office, his young bride turned to a member of the White House staff and said: 'I want you to take good care of all the furniture and ornaments in the house, for I want everything just as it is now when we come back again. We are coming back. Just four years from today'

Donald’s third wide, Melania Trump flirted with the idea of becoming First Lady again in a 2021 interview with Fox News where she was asked if she could see herself back in the White House and she replied: ‘Never say never.’ Likewise, on Grover Cleveland’s final day in office, his wife turned to a member of the White House staff and said: ‘I want you to take good care of all the furniture and ornaments in the house, for I want everything just as it is now when we come back again. We are coming back. Just four years from today’

Cleveland was a bachelor when he entered the White House, and became the only sitting president to be married during his presidential term when he wed 21-year-old Frances Folsom at age 49. She was the youngest First Lady in American history and the couple had five children together.

Some historians have pointed to Trump’s propinquity for celebrated beauties having owned the Miss America pageant, and perhaps more scandalously, his friendship with the disgraced pedophile financier, Jeffrey Epstein. 

Trump has been married three times, first to Ivana Trump, mother of his three eldest children: Donald Jr., Eric, and Ivanka. Their marriage became tabloid fodder when Trump was caught having an affair with  26-year-old beauty queen, Marla Maples.

One headline reported that Maples said ‘she had the best sex of her life’ with Trump and the couple was married in 1993, two months after the birth of their only daughter, Tiffany. 

The doomed relationship eventually ended in divorce in 1999, and paved the way for Trump’s third marriage to Melania Trump, a Slovenian model that he met during his breakup with Maples. 

Melania officially became wife number three in 2005, and the couple share one son, Barron Trump, born in 2006. 

From the Tennis Pavilion to the Rose Garden, Mrs. Trump worked on a variety of restoration projects during her tenure as First Lady. 

By the same token, on Grover Cleveland’s final day in office, his young bride turned to a member of the White House staff and said: ‘I want you to take good care of all the furniture and ornaments in the house, for I want everything just as it is now when we come back again. We are coming back. Just four years from today.’

Four years later, she was right. 

Only time will tell if Melania will reassert her position at 1600 Pennsylvania Avenue. 

In her first sit-down interview since leaving Washington in January 2021, she told Fox News: ‘I think we achieved a lot in four years of the Trump administration.’ When asked if she could see herself back in the White House, she responded: ‘Never say never.’

Trump's marriage to his first wife, Ivana Trump ended when he was caught having an affair with 26-year-old beauty queen, Marla Maples

Trump’s marriage to his first wife, Ivana Trump ended when he was caught having an affair with 26-year-old beauty queen, Marla Maples 

Trump's sensational affair to Marla Maples became tabloid fodder when she famously told the press that 'she had the best sex of her life' with Trump. The couple married in 1993, two months after the birth of their only daughter, Tiffany (pictured as a child). Their doomed relationship eventually ended in divorce in 1999, and paved the way for his third marriage to Slovenian model, Melania Trump

Trump’s sensational affair to Marla Maples became tabloid fodder when she famously told the press that ‘she had the best sex of her life’ with Trump. The couple married in 1993, two months after the birth of their only daughter, Tiffany (pictured as a child). Their doomed relationship eventually ended in divorce in 1999, and paved the way for his third marriage to Slovenian model, Melania Trump

Despite his close ties to Jeffrey Epstein and convicted sex trafficker, Ghislaine Maxwell, Trump managed to clinch the 2016 election against his Democrat opponent, Hillary Clinton

Despite his close ties to Jeffrey Epstein and convicted sex trafficker, Ghislaine Maxwell, Trump managed to clinch the 2016 election against his Democrat opponent, Hillary Clinton 

A tale of two election losses: How Cleveland conceded defeat to his political adversary while Trump promoted false claims of election fraud  

Cleveland was indifferent about running again in 1888. When he won the Democratic primary, he told a friend: ‘I sometimes think that perhaps more enthusiasm would have been created if somebody else had been nominated after a lively scrimmage at St. Louis.’  

His campaign was inevitably hurt by lack of funds and his perceived ‘lethargy’ throughout the run, which paved the way for his Republican opponent, Benjamin Harrison’s victory.  

Harrison, a former Civil War general and senator from Indiana, was also the grandson of President William Henry Harrison. He lost the popular vote to Cleveland by a small margin (47.9 percent to 48.6 percent) – but won big in the electoral college (233 to 168) which sealed his path to the White House. 

Unlike Trump, Cleveland accepted his 1888 loss with grace aplomb, in spite of dubious suggestions by his supporters of electoral fraud in the state of Indiana. He wrote a letter to the President-elect indicating his desire ‘to assure you of my readiness to do all in my power to make your accession to office easy and agreeable.’ And went so far as attending Harrison’s rainy inauguration ceremony while holding an umbrella as he delivered his inaugural address. 

By contrast, Trump lost the popular vote to Biden, 46.8 percent to 51.3 percent and also failed to harness enough votes in the electoral college.     

He has still yet to accept his 2020 defeat and continues to promote false allegations of election fraud – despite the Supreme Court having rejected a handful of election challenge cases. His public campaign to undermine the validity of the 2020 election culminated on the January 6 insurrection and attack of the U.S. Capitol. 

Staging a political comeback motivated by boredom 

In retirement, Cleveland and his wife moved to New York City, where the former president enjoyed card games with friends, attending vaudeville shows and going out to restaurants. He was known to be a gourmand, and weighed approximately 300 pounds.

During this time, he also became a father for the first time and told an associate that he felt as though he ‘had entered the real world’ for the first time.

But like many ex-politicians who give up the game to enjoy life as a private citizen, Cleveland quickly grew bored, and according to Politico, ‘boredom’ was his primary motivation for running a third time.

The path to a 2024 victory for Donald Trump seems less clear that Cleveland's in 1892. The ex-commander in chief came under attack by establishment Republicans after the massive 'red wave' failed to materialize in this November's midterm elections. And thus, it remains to be seen what Trump's platform for the 2024 race will entail. If his announcement speech is any indication, combatting inflation seems to be at the top of his priorities

The path to a 2024 victory for Donald Trump seems less clear that Cleveland’s in 1892. The ex-commander in chief came under attack by establishment Republicans after the massive ‘red wave’ failed to materialize in this November’s midterm elections. And thus, it remains to be seen what Trump’s platform for the 2024 race will entail. If his announcement speech is any indication, combatting inflation seems to be at the top of his priorities

The 1890 midterm elections showed promise when his party of Democrats won sweeping victories at the ballot boxes. His Republican opponent, Benjamin Harrison had become deeply unpopular with voters and Cleveland saw a path to re-election.  

Cleveland overwhelmingly won the primary during the 1892 Democratic convention in Chicago, in part because he emphasized economic stability when the economy was plagued by inflation. 

According to the Wall Street Journal, the third-time presidential hopeful crawled his way back to the White House by defying his own voters. ‘In 1891, as populists agitated to flood the country’s monetary system with silver—’to inflate away the debt burden on Western and Southern Democrats’—Cleveland issued an open letter warning of the policy’s potentially ruinous effects.’

The path to a 2024 victory for Donald Trump seems less clear. The ex-commander in chief came under attack by establishment Republicans after the massive ‘red wave’ failed to materialize in this November’s midterm elections.

And thus, it remains to be seen what Trump’s platform for the 2024 race will entail. But if last night’s speech is any indication, combatting inflation seems to be at the top of his priorities.

‘We are a failing nation for millions of Americans,’ he said in his announcement speech. ‘The past two years under Joe Biden have been a time of pain, hardship, anxiety and despair. As we speak, inflation is the highest in over 50 years. Gas prices have reached the highest levels in history and expect them to go much higher.’ 

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