The Historical Parallels Between Donald Trump and Grover Cleveland

The 45th and 47th President of the United States Donald Trump (L) and the 22nd and 24th President of the United States Grover Cleveland (R)
Collage by Hungarian Conservative
Donald Trump and Grover Cleveland are the only two presidents in US history to have been elected to non-consecutive second terms. However, as it turns out, it is not the only thing the two statesmen serving in the highest office in the land have in common.

With Congress certifying his election victory in the 2024 US presidential election, it is official: Donald Trump is the second President in United States history to be elected for a non-consecutive second term. The only other man to have achieved that has thus been mentioned a lot lately: the 22nd and 24th president, Grover Cleveland.

As it turns out, it is not the only similarity between the two statesmen serving in the highest office of the land over a century apart. Here is a list of the historical parallels between them.

They Were Both New Yorkers

This first statement only holds true if we apply two different definitions for the word ‘New Yorker’. Cleveland was born in Caldwell, New Jersey in 1837. He is also buried in New Jersey, in Princeton. However, all the public offices he held during his life were in New York: from Sheriff of Erie County to the Governor of the state. Typically, for presidents and presidential candidates, it is the state that elected them to public office that counts as their home state.

Donald Trump, on the other hand, is a bona fide New Yorker, born and raised in New York City. He was born in Queens borough in 1946. The Trump Organization which he has been chairing since 1971 has always been based in New York City as well. He had never held any public office before he ran for president. He did flirt with the idea of running for Governor of New York as a Republican in 2014, but ultimately decided not to go through with it. However, ahead of the 2020 election, he moved his campaign headquarters to Palm Beach, Florida and made his Mar-a-Lago estate his primary residence as well.

They Were Both Outsiders Running on an Anti-Corruption Platform

Grover Cleveland was considered a dark horse, outsider candidate in the 1884 presidential election because of his rapid ascend on the political ladder. It had only been three years prior that he had been elected as the Mayor of Buffalo, an office in which he served less than a year, as in 1882, he was elected Governor of New York. He did not spend much time in the Governor’s Mansion in Albany either, as in 1884, he was first selected as the Democratic Party’s candidate, then won the election against Republican James G Blaine, a highly experienced Senator and former Speaker of the House from Maine.

Grover Cleveland, the Only President to Win a Non-Consecutive Term — The Election of 1892

Efforts for civil service reforms originally started on the Republican side in the 19th century, but Cleveland picked up that torch on the Democratic side, and made the fight for merit-based and not political appointments a part of his campaign. Blaine was in agreement with him on that issue, but he was caught up in a corruption scandal of his own, which greatly hurt his credibility on this matter.

Donald Trump is the only president in US history not to serve in an elected or appointed public office, or in any military position prior to being elected president. In that regard, he is the biggest outsider ever to hold that office. Throughout all three of his presidential campaigns, he rallied against government corruption. He typically used the phrase ‘Drain the Swamp’ to call for anti-corruption government reforms. He also often spoke of ‘the Deep State,’ a group of long-serving, unelected government officials in Washington DC who can halt popularly mandated change.

They Were Both Overweight

Grover Cleveland is the second heaviest POTUS in history, only behind William Howard Taft. He weighed around 260 pounds (118 kilograms) at the time he was serving. Given that he stood at 5’11 (180 centimetres) tall and was not particularly muscular, he was seriously overweight. A few surviving pictures at the time, however, suggest that this was not the case when he was a young adult.

Donald Trump follows him on the presidential weight list, with around 240 pounds (108 kilograms) during his first term in office. However, he is significantly taller than Cleveland was (6’3, 190 centimetres) and has significantly more upper body muscle mass as well, based on photographic evidence. Still, President Trump too has been clearly overweight throughout his political career, which he started late in his life.

Both of Their First Vice Presidents Were Governors of Indiana

Both Cleveland and Trump had different Vice Presidents serving under them in their first and second terms. However, their reasons for the switch were different.

Cleveland’s first VP, Thomas A Hendricks, died in office in November 1885. As per the rules at the time, the Vice Presidential office was left vacant until the remainder of the term. Donald Trump, on the other hand, had a falling out with his first VP, Mike Pence, over the certification of the 2020 presidential election results which he believed to be fraudulent. As President of the Senate, it is the sitting Vice President who certifies each presidential election result. Thus, Trump chose Ohio Senator JD Vance to be his running mate in the 2024 election.

Interestingly, both Hendricks and Pence were governors of Indiana, with the former serving in the office between 1873 and 1877; and the latter serving in the office between 2013 and 2017. This makes more sense in the case of Cleveland, as Indiana was a swing state at the time. In 2016, however, Indiana was considered a safe Republican state.

Grover Cleveland had an illegitimate child when he was 36 years old. He too ultimately admitted this, and emphasized during his campaign that the boy was taken good care of by his foster family that he had found for him. Evidently, that did not stop the Republican operatives in the press from mocking him with the chant ‘Ma, ma, where’s my pa,’ painting him as an absentee father. Cleveland also tried to deflect the blame by painting the mother of his child, a woman named Maria Halpin, as immoral and promiscuous, who evilly seduced him. Halpin, however, claimed the exact opposite, and stated that Cleveland had raped her, and used his power as Sheriff of Eerie County to commit her in a mental asylum to stop her from pressing charges.

Political cartoon from The Judge magazine in 1884, mocking Grover Cleveland for his illegitimate child. PHOTO: Wikimedia Commons

President Trump’s sex scandals seem tame by comparison. During the 2016 presidential election, a ‘hot mic’ recording of him was released, in which he talks crudely about women to TV host Billy Bush. At that time, Donald Trump also paid porn star Stormy Daniels $130,000 in ‘hush money’ to keep quiet about his extramarital affair with her in 2006. Since he mislabeled that payment as attorney’s fees, this later led to his conviction on 34 felony counts of falsifying business records in May 2024. Thus Trump became the first president in US history to be convicted in criminal court.

Tariffs Were a Major Issue for Both of Them

This is a bit of a spin job, as Cleveland and Trump were on the exact opposite ends of the spectrum on the issue of tariffs.

As a ‘Bourbon Democrat,’ Cleveland believed in facilitating free trade as much as possible, and thus keeping tariff rates as low as possible. He dedicated his entire 1888 State of the Union address to the issue of lowering tariffs, which some believe cost him the narrowly lost election that year, as he neglected other issues. President Trump, on the other hand, likes to threaten high tariff rates to coerce other countries into doing what he wants to do. In 2019, during his first term in office, he actually raised tariff rates significantly, which were lowered in 2020 during the COVID-19 pandemic.

This fact is not unusual for Cleveland, as, prior to a federal income tax, tariffs were the primary source of income for the federal government, and thus were always a major issue in presidential campaigns in the 19th century. In the 21st century, however, Donald Trump has been the president who brought up the issue the most by far.


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Donald Trump and Grover Cleveland are the only two presidents in US history to have been elected to non-consecutive second terms. However, as it turns out, it is not the only thing the two statesmen serving in the highest office in the land have in common.

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