Is History Repeating Itself with Trump’s Election?

You may have seen the somewhat forced comparisons between Abraham Lincoln and John F. Kennedy. They go something like this…

• Both presidents were elected to Congress in '46 and later to the presidency in '60.
• Both married in their 30s to women who were in their 20s.
• Both of their assassins, John Wilkes Booth and Lee Harvey Oswald, were born in '39 (actually Booth was born in 1838, not 1839) and were known by their three names, composed of fifteen letters.
• Both presidents were shot in the head on a Friday and in the presence of their wives.
• After shooting Lincoln, Booth escaped from a theater to a warehouse (barn). Oswald shot Kennedy from a warehouse and was captured in a theater.
• Both of the presidents' successors were Democrats named Johnson with six-letter first names and born in '08.
• Lincoln had a secretary named Kennedy (actually, he had two secretaries, but their names were Hay and Nicolay) who told him not to go to Ford's Theatre. Kennedy had a secretary named Lincoln who warned him not to go to Dallas.
• Both Oswald and Booth were killed before they could be put on trial.

Historical coincidences are nothing new. Likewise, conspiracy theorists who like to pound a square peg into a round hole abound just as frequently.
That being said, there are some rather interesting similarities between the only two U.S. presidents to be elected to two nonconsecutive terms, Grover Cleveland (22 & 24) and Donald Trump (45 & 47).

First, although Cleveland was born in Caldwell, NJ and died in Princeton, NJ, he spent the vast majority of his life and political career in New York State. Trump, who was born and raised in the Borough of Queens in New York City, maintained his legal residence in the Empire State until 2019, when he changed his official residency to Florida.

Second, both men were haunted by past indiscretions during their presidential campaigns. In 1884, Cleveland was accused of fathering an illegitimate child while he was a lawyer in Buffalo. “Ma, Ma, where’s your Pa?” became an attack line against Cleveland (and after his election, the punch line “Gone to the White House, ha, ha, ha!” was added). As for Trump, we are all familiar with the nonstop allegations about his personal behavior, but his only admitted affair was with Marla Maples that led to his divorce from Ivana, his first wife, in 1990.

Third, both Cleveland and Trump had five children and eventually married much younger women. Ivana Trump, the mother of Donald’s first three children, was only three years younger than him. However, Marla Maples (Tiffany’s mother) is 17 years his junior and Melania Trump (Barron’s mom) is 24 years younger than her husband. Meanwhile, Cleveland entered the White House as a bachelor but married two years later. He was 49 years old at the time of their Blue Room wedding and Frances, his young bride, was only 21.

Fourth, both Cleveland and Trump were seen as anti-establishment reformers. Cleveland, as Governor of New York, took on the powerful (and very corrupt) Tammany Hall Democratic machine, which controlled New York City politics and patronage for more than 100 years, from the 1850s to the 1960s. For his part, Trump has promised to “clean the swamp” in Washington… and by bringing Elon Musk and Vivek Ramaswamy (and potentially Pete Hegseth and RFK Jr.) into his administration, he appears to be well on his way.

Fifth, during Cleveland’s first presidential campaign, he successfully won all four swing states: New York, New Jersey, Indiana, and Connecticut. However, four years later, he only won two of them while losing his home state of New York and Benjamin Harrison’s home state of Indiana. In his 1892 rematch with Harrison, Cleveland again won all four swing states… and the presidency.

Likewise, Trump swept the Democratic “Blue Wall” in his 2016 win over Hillary Clinton, but saw Joe Biden narrowly reclaim Pennsylvania, Michigan, and Wisconsin in 2020. Earlier this month, Trump flipped them back to “red” on his road back to 1600 Pennsylvania Avenue.

One area in which the two men strongly differed is tariffs. Cleveland hated them and fought them every chance he got, going as far as making his free trade position a cornerstone of his 1892 campaign. Conversely, President Trump openly supports tariffs and sees them as an effective international bargaining tool.

A final thought…

Shortly after Cleveland re-entered the White House, the Panic of 1893 plunged the stock market – and the entire country – into a deep economic depression. Let’s hope and pray that, at least as far as the economy is concerned, history won’t repeat itself.