Donald Trump Is All The Worst Parts of Thomas Jefferson

 And none of the best.

I’ve been thinking about how to write about the new president, and how to relate him to the founding fathers. I keep coming back to Thomas Jefferson.

Jefferson was an incredible person whose contributions to the United States were enormous, but he was also full of contradictions and deep flaws. The more I thought about Donald Trump, the more I realized that he reminds me of Jefferson. Specifically, the bad parts. Actually, only the bad parts.

These are the best and worst qualities of the third US president, and how the forty-fifth matches up.

Thomas Jefferson’s Best Qualities, Which Donald Trump Utterly Lacks

#1. Intellectual Curiosity

Jefferson is known for his brilliance – John F. Kennedy famously said at a Nobel Prize Winners dinner, “I think this is the most extraordinary collection of talent, of human knowledge, that has ever been gathered together at the White House, with the possible exception of when Thomas Jefferson dined alone.”

To me, Jefferson’s intelligence is not nearly as admirable as his intellectual curiosity. A voracious reader who donated his 6,000 volume library to the Library of Congress, Jefferson became a man who “could calculate an eclipse, survey an estate, tie an artery, plan an edifice, try a cause, break a horse, dance a minuet, and play a violin.”

Trump, who has said he is “like, very smart,” does not read books. “I read passages, I read areas, I’ll read chapters, I just don’t have the time.” He said his two favorite books are two he has written, and one of the only books he is known to have read is a book of Hitler’s collected speeches.

Thomas Jefferson’s love of learning led him to found the highly-esteemed University of Virginia, which is known for its innovation. Donald Trump’s love of money led him to found the fraudulent Trump University.

Utterly lacking the intellectual curiosity required for personal growth, Trump doesn’t seek out knowledge because facts might get in the way of his gut instincts and narcissism.

2. Freedom of Religion

One of Thomas Jefferson’s proudest accomplishments was authoring the Statute of Virginia for religious freedom; he wanted it listed just above “Father of the University of Virginia” on his gravestone. He was a strong proponent of the separation between church and state, and believed people should have the right to practice – or not practice – whatever they wanted. He wrote that “it does me no injury for my neighbour to say there are twenty gods, or no gods. It neither picks my pocket nor breaks my leg.” 

Donald Trump seems to believe only in the freedom of his own religion. He claims to be a Christian but has never asked for forgiveness, though he enjoys the cleansing feeling “when I drink my little wine and have my little cracker” at communion. Depending on his audience, he has also offered The Bible as his favorite book (“Two Corinthians” in particular). His favorite verse is “an eye for an eye,” which as a policy was explicitly repealed by Jesus who said to instead “Turn the other cheek.” But Trump only reads parts and areas of books, so he probably hasn’t made it to that part of his favorite book yet.

Being familiar with The Bible is not a requirement to be president, but adhering to the Constitution certainly is. Trump’s blatant disregard for the Constitution’s freedom of religion should alarm everyone. His proposed ban on Muslims and campaign talk of Muslim registration is terrifying not only because of its moral implications, but also because it would vindicate our terrorist enemies and increase their recruitment, making the world a far more dangerous place. He might know that if he read books.

3. Freedom of the Press

When a Prussian visitor to Jefferson’s White House noticed a newspaper filled with vile statements about Jefferson, he asked, “Why is not this libelous journal suppressed, or its Editor at least, fined and imprisoned?” Jefferson smiled and replied, “Put that paper in your pocket Baron, and should you hear the reality of our liberty, the freedom of the press, questioned, show this paper, and tell where you found it.” Jefferson wasn’t perfect when it came to freedom of the press, but he was proud of it as an American institution – no matter what Trump says.

Donald Trump’s relationship with the press and his abhorrence of dissent are extraordinarily un-American for someone sworn to uphold an oath to the Constitution. The first amendment clearly states “Congress shall pass no law…abridging the freedom of speech, or of the press” but Trump still wants to open up libel laws to make it easier to sue new outlets who print stories he considers hit pieces.

Unflattering reports and dissent, to him, are libelous and those responsible must be humiliated and made to suffer, like the author who wrote a book purporting Trump was not as wealthy as he claimed. Trump tried to sue him for five billion dollars, but the case was dismissed because that’s not how the law works. Not now anyway. Imagine how much money Trump could get if he had some influence on the law.

4. Communication

Extremely non-confrontational and polite in person, Thomas Jefferson instantly put his conversational partners at ease with his soft voice and genuine interest in what they had to say. That disarming charm made him a skilled diplomat and dealmaker. He brought people together at intimate dinner parties, and senators previously opposed to his agenda were later heard saying “the President’s dinners had silenced them.”

Respect is an essential trait for an effective leader, and Jefferson knew that. Brute force and intimidation might be effective in the short-term, but it burns more bridges than it builds. The ROI on bullying is always negative, eventually.

Donald Trump might not agree, and so far he seems to be getting ahead with his “winning temperament,” which in reality is the loud, boisterous, thin-skinned, incoherent, and impetuous behavior of a spoiled child. Words, to him, are blunt objects that are not so much chosen as they are hurled.

He claims to have “the best words,” but in his writing (tweeting) and speeches, he generally employs a third-grade level vocabulary. Like a sitcom character, he has his favorite words and catchphrases (Tremendous, Sad, Losers, etc.) that lend itself to their own refrigerator poetry kit which I recommend if you’re trying to lose weight, you fat failing pig.

Thomas Jefferson’s gift with words is legendary. His love letters read like poetry, and his personal letters are master courses in the art of manipulation. Today he is best remembered as the author of the Declaration of Independence.

That cry for freedom is a far cry from Trump’s first foray into political writing. In a 1989 full-page ad he paid for in four New York City newspapers, he called for the execution of five teenagers accused of a horrific rape in Central Park. In it, he wrote, “Criminals must be told that their CIVIL LIBERTIES END WHEN AN ATTACK ON OUR SAFETY BEGINS!” The problem is they were innocent. Even after the black and Latino men were exonerated based on DNA evidence, Donald Trump still, to this day, clings to the belief that they must be guilty of something even though they had no criminal records.

That brings us to the qualities of Thomas Jefferson that Donald Trump shares – the bad ones.

Thomas Jefferson’s Worst Qualities, Which Donald Trump Magnifies

1. Racism

When Thomas Jefferson wrote that all men are created equal, he meant white men. As a slaveholder his entire life, he often lamented slavery but did nothing to address the problem – both because it might have hurt his popularity and ability to effect other change, and because he held unquestionably racist views. In some ways he invented racism by attaching a bogus scientific rationale for it, claiming among other things that blacks were less intelligent and smelled worse than whites, and that they mated with orangutans. This may be part of why he never freed his slaves, even though his Virginia neighbors (like George Washington) did.

Trump’s racism and bigotry is well-documented. He was sued twice for discriminating against blacks, declared that a judge was unfit to try a case against him because he was Mexican, and consistently believes that all African-Americans live in hellish inner-cities.

His major entry into politics is also based on racism, although many would disagree. For anyone familiar with modern racism, it’s hard to consider Trump’s birtherism as anything else. Trump waged a years-long crusade to delegitimize the first black president by questioning his place of birth, even after Obama released his long form birth certificate. Trump rose to political prominence in the United States based on a racist lie.

Jefferson’s legacy will always be tainted by slavery because his actions advocated it even though his rhetoric denounced it, but his legacy includes much more than this significant blight.

The full role of racism and white nationalism – of hate – in Trump’s legacy remains to be seen, but much of the damage is already done. Trump effectively showed Americans that hate is a virtue. He told us our problems were because of others. Immigrants. Mexicans. Muslims. He used scapegoats to incite fear and anger among throngs of chanting followers at rallies, and what’s worse is that he convinced millions of people there was nothing wrong with that.

2. Trouble With Women

Thomas Jefferson was the first president to have sex scandals. The most infamous and despicable was his relationship with his slave, Sally Hemings, with whom he fathered six children. But that wasn’t the only one.

Jefferson also went after multiple married women including his best friend’s wife, Elizabeth Walker. He once feigned sickness at a party so he could sneak into her bedroom uninvited. He later admitted this indiscretion, saying it was “an incorrect thing to do” and attesting that Elizabeth honorably refused him.

Like Jefferson, Donald is no stranger to going after married women, except he’s not one for apologies…or anything resembling honor. The lecher who bragged about leering at beauty pageant contestants in their dressing rooms also bragged about using his stardom to commit sexual assault.

His first wife, Ivana, accused him of brutally assaulting and raping her following a painful scalp reduction surgery. His lawyers got a statement from her clarifying that claim – she “felt violated” but did not want her words “to be interpreted in a literal or criminal sense.” So one might say that he brutally and figuratively – but totally legally – raped her. Since then at least a dozen more women have accused him of sexual assault.

Donald Trump’s problem with women extends beyond physical assault to a mindset of sexism which is rampant and reprehensible. Trump says “Nobody has more respect for women than I do,” but what he considers respect for women is, at best, objectification. Women exist to please and serve men, and it is not their place to challenge men. If they understand this and do their duty arousing him, he considers them beautiful – nice pieces of ass. If they step outside their role, they are ugly fat pigs. They are nasty.

3. Fatherhood

I wouldn’t question Thomas Jefferson’s love and adoration for his children and grandchildren (the ones he didn’t keep as slaves, anyway), but his parenting style left much to be desired.

When he went to France to serve as minister, he left his 2-year-old and 6-year-old daughters behind. It was only after his youngest died of whooping cough that he sent for his oldest, who didn’t want to leave her aunt and had to be tricked into getting on the ship to Europe.

He also gave some pretty gross beauty advice to her when she was 11: “A lady who has been seen as a sloven or a slut in the morning, will never efface the impression she then made with all the dress and pageantry she can afterwards involve herself in. Nothing is so disgusting to our sex as a want of cleanliness and delicacy of yours.

Trump’s daughters also grew up with their father as a distant figure, even when he lived in the same house. He has said he won’t put kids to bed, change their diapers, or take them to the park. “I won’t do anything to take care of them,” he has said. “I’ll supply funds and she’ll take care of the kids.”

Maybe that minimal role in their upbringing prevented him from bonding with them enough to identify with them as kin, and that’s why he treats them like he treats all women – as existing solely for the sexual pleasure of men.

He doesn’t mind if you call his daughter Ivanka “a piece of ass.” He has often said that if she weren’t his daughter, he might be dating her. “You know who’s one of the great beauties of the world, according to everybody?” he once asked. “And I helped create her. Ivanka…She’s got the best body.” He once lamented, “If I weren’t happily married and, ya know, her father…”

When his daughter Tiffany was a baby, he was asked what attributes she had of her parents. He responded, “She’s got Marla’s legs. We don’t know whether or not she’s got this part yet,” he said, making a big-bosomed gesture. He could have named anything about her, but he went to his default and objectified his baby daughter because one day she would grow into a woman.

Trump is a disturbing, disgusting, and demeaning example of fatherhood.

4. Money Troubles 

Thomas Jefferson was a bona fide shopaholic who spent beyond his means and had so much debt that he had trouble getting loans. Biographer David McCullough said Jefferson kept meticulous records of every purchase and expenditure but “it was as if somehow he could never bring himself to add up the columns.” On his farm, “he never in his life added up the profit and loss for any year, and perhaps for the reason that there was almost never any profit.”

Trump has similar problems with debt, even though both he and Jefferson benefited from free labor – Jefferson by owning over 600 slaves, and Trump by not paying his contractors. Six of Trump’s companies have filed for bankruptcy and his companies have over $700 million dollars in debt that we know of.

Trump’s problem with money is much more profound than debt. For him, wealth is his defining characteristic. It’s the most important thing to him, and the only thing he wouldn’t let comedians make fun of in his 2011 Comedy Central roast. His hair, his weight, his wives, his failed business, his sexual attraction to his daughter – all of those areas were fair game he said, but do not joke that he has less money than he claims.

His actual money situation is unclear because he refuses to release his taxes and he makes up his net worth based on how he’s feeling. We actually know far more about Thomas Jefferson’s finances than we do Donald Trump’s, and there’s a good reason for that.

Much of Trump’s income comes from licensing his name to properties he does not own, like the Trump SoHo. His name is a brand, and it has value because it is associated with great wealth. If that wealth were to be questioned, then the actual value of the brand could go down. He’s like a pecuniary Rumpelstiltskin – if you say his true net worth, his brand shrivels up.

It seems unlikely than any oath of office would supersede the allegiance he has already pledged to his brand.

5. Deceit

Many founding fathers are rightly considered honest men. Thomas Jefferson is not one of them.

As secretary of state, Jefferson actively worked to undermine the government he served by secretly founding a party to oppose President Washington’s policies. He even started a newspaper to smear the Federalists and got the government to pay for it by hooking up its editor with a questionable state department job as a translator.

Then, as John Adams’s vice-president, he secretly authored the Kentucky Resolution, a bill giving states the right to nullify any federal laws they deemed unconstitutional. It was an insidious idea, threatening the very nation he helped found, and laying the groundwork for the south’s secession and the Civil War.

Jefferson at least tried to hide his duplicity, and in some cases it wasn’t until years after his death that the full extent of his machinations were known. Donald Trump’s deceit is flagrant. Politifact determined that he is lying 85% of the time, especially about immigration, crime rates, and the condition of our cities. He lies to scare people so they believe he alone can protect them. He lies to attain and maintain power.

As despicable as Jefferson’s actions were, they were in service of what he thought was best for the country. Trump’s deceit is in service of his own ego, and his desire to retaliate against dissent. It doesn’t matter to him if something is true or not, as long as his most ardent followers believe it. If a reporter or a union boss says something he doesn’t like, he tweets about it. The subjects of those tweets soon find themselves on the receiving end of death threats. Donald Trump cannot be trusted with money, women, or words, so it may be wishful thinking to believe he can be trusted with his ability to weaponize fanatic supporters.

One of Thomas Jefferson’s most admirable moments was during his first inauguration when he tried to pull a fractious nation together by saying (too softly for anyone to hear), “We are all Republicans, we are all Federalists.” Bridging that divide will be harder for Trump, who refers to his political opponents as his “enemies.”

Donald Trump could learn a lot from Thomas Jefferson as he takes on the presidency, but I doubt he will because he’s never read a biography of a president.

In the course of his 34,000+ tweets, however, Trump has quoted Jefferson twice:
Of course, Thomas Jefferson never said either of these things.

The first quote comes from the diary of Polish writer Witold Gomborwicz, published in 1988.

The second is from an 1860 biography of Andrew Jackson. Historian Daniel Feller said the biographer, whose full quote was actually “Desperate courage makes one a majority,” was no fan of Jackson’s. In fact, he thought of him as “a headstrong ignoramus whose desperate courage overrode other men’s good sense.”

In Trump’s case, “desperate courage” doesn’t quite apply. Desperate bravado is more fitting. That’s something the White House has seen before, but it will never be filled with more of it than when Donald Trump dines alone.


Thomas Jefferson: The Art of Power by Jon Meacham, Jefferson and the Rights of Man by Dumas Malone, Jefferson: A Revealing Biography by Page Smith, John Adams by David McCullough




  1. December 9, 2018 / 8:29 am

    Excellent essay. I am encouraged that there is hope for our nation when I see thoughtful critiques like these. And since I am married to a Trump supporter, it helps to find those who validate my opinions of our president (lower case intentional).

    • Howard Dorre
      December 13, 2018 / 4:07 pm

      Thank you for reading! Here’s hoping the country (and your marriage) survive these trials!

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