Haaaaay! I’m back, y’all!
Did you miss me?
Did you catch up on Adams?
Did you comment on my post?
Are you ready for some MESS?
Because okay.
Remember how I read all SIX HUNDRED AND FIFTY-TWO pages of John Adams and was like:
Never again.
Well.
I was loud and wrong.
Because here came Thomas Jefferson with FIVE HUNDRED AND THIRTY-FIVE pages of biography and NINE. TEEN. PAGES. of notes.
NINETEEN.
So I highly recommend you get a snack, a drink of choice, maybe stretch first, and settle in.
And before y’all panic?
It’s okay.
I already checked out my Madison biography from the library.
And while multiple sources insisted the best Madison biography was another 600-page absolute unit, I said:
OH NO, MA’AM.
This Madison biography is a very respectable 250 pages.
Growth. Boundaries. Healing.
…except I can’t even fully commit to that joke because I ALSO checked out another 600-page book for a completely different history side project I want to start this summer.
(More on that later. 🤣😰😭)
But this post felt different, y’all.
Jefferson had me turned every which way but loose.
One minute I was impressed.
Then furious.
Then disgusted.
Then genuinely surprised.
Then annoyed.
Then completely over his nonsense.
Then puzzled.
And somehow, occasionally, impressed again.
A deeply exhausting man.
And biographer too. But again… we’ll get there.
My hope is that by the time you finish reading this, you’ll either be:
- staring off into the void
- wanting to throw your laptop directly into the garbage
- immediately rereading certain sections
- or some deeply concerning combination of all three
So stay with me.
Because it’s going to be a bumpy ride.
But I promise…
we’ll make it out the other side.
The Man: A Brief Bio
Say it with me now — And I do mean brief.
Because if I tried to cover every corner of Thomas Jefferson’s life in detail, this post would somehow become longer than the Declaration of Independence, the Constitution, and all the biographies written about him combined.
Thomas Jefferson was born April 13, 1743, in Virginia, into the planter class.1Reminder the planter class? Yeah, the same one Washington was born into.
So unlike Adams who always felt like the smart outsider trying to prove himself, Jefferson was starting life with a very different hand.
He had land. He had status. He had connections.
Money? Was a little funny. And we’ll get to that later.
But access? Absolutely.
His father died when Jefferson was fourteen, and from an early age he stepped into adult responsibilities — helping manage family affairs while also developing what would become one of the defining characteristics of his life:
This man loved to LEARN.
Books. Languages. Science. Architecture. Philosophy. Agriculture. Music.
If there was knowledge to be collected, Jefferson wanted it. 👀
At William & Mary, Jefferson developed a deep commitment to reason, learning, and questioning the world around him.
He was disciplined, very curious, and by all accounts brilliant.
He was also apparently maintaining “a little too showy style of living.”
So, we have a nerd who liked luxury.
Jefferson studied law, passed the bar in 1765, and practiced successfully enough — but law never really seems to have been where his heart was.
He was much more interested in science, political theory, and ideas.
Which tracks.
Because Jefferson doesn’t strike me as someone that interested in people so much as someone fascinated by systems.
And, perhaps more importantly, by how to move within them.
Even in how he presented himself, Jefferson could be… slippery.
He was soft-spoken, tactful, polite, and rarely openly confrontational. Which sounds nice.
Except apparently this tendency was so pronounced that some people thought he was two-faced — mistaking his polite nodding for agreement when really he was just avoiding direct conflict.
And listen, I know some people are just conflict-averse. Not everybody is built like John Adams who stayed ready to debate anyone at anytime over anything.
But with Jefferson, it starts to feel a bit different.
Because over time, this habit of saying very little directly while doing quite a lot behind the scenes started to read less like politeness and more like strategy.
But I’m getting ahead of myself.
For now, just know this man knew how to present himself.
One woman later described him as “meek and mild, yet dignified,” with a soft voice and a warm, intelligent face. He apparently had a way of drawing people into conversation and making them talk about themselves in ways they hadn’t intended.
And you know what we would call that?
Elite politician behavior.
Because for all the images of Jefferson as the quiet intellectual tucked away with his books, the man absolutely knew how to work a room when he wanted to.
He married Martha Wayles Skelton when he was twenty-eight. She was a young widow, and by all accounts, he deeply loved her. Later, he described their marriage as ten years of “unchequered happiness.”
When she died after years of illness, Jefferson was devastated — emotionally wrecked enough to withdraw from public life entirely for a time, and bound by a promise never to remarry.
Which he kept.2In a manner of speaking. 👀
And this becomes a pattern.
Because throughout his life, whenever public pressure intensified, Jefferson’s instinct was often to retreat.
To Monticello.
To books.
To private correspondence.
To spaces where he could think rather than perform.
But what makes Jefferson fascinating is that even with that instinct toward withdrawal, he was never truly removed from power for long.
Because underneath the soft-spoken manners, the intellectual curiosity, and the carefully managed image was a man who cared deeply about influence.
His own.
His country’s.
And how history would remember both.
Thomas Jefferson may have seemed mild.
But he was never passive.
The Revolutionary
Jefferson was not Washington.
He was not out here charging into battle, having horses shot out from under him, collecting action hero lore.
And he was definitely not John Adams, talking everyone into exhaustion.
Jefferson’s weapon was the pen.
And LORD did he know it.
Jefferson’s entry into revolutionary politics came through Virginia’s House of Burgesses — basically colonial Virginia’s version of a state legislature.
So imagine lawmakers arguing about taxes, power, and who gets to make decisions… except all of them still technically answered to Britain.
And hovering over all of that was the royal governor — the king’s appointed representative in Virginia. Think “governor,” but with significantly less democracy.
As tensions with Britain kept escalating, the governor shut the whole thing down after lawmakers supported colonial resistance.
Jefferson helped draft the colony’s response.
And just like that, he was no longer just a smart guy with opinions.
People started noticing him and the amazing gift he had.
Specifically: writing.
The man was lethal with a pen.3 Read: quill
At just thirty-three years old, Jefferson became the youngest member of the committee tasked with drafting the Declaration of Independence.
Not because he was the most experienced.
Not because he had the loudest voice in the room.
But because everybody knew that if you needed something to sound smart, principled, and revolutionary as hell?
Jefferson was your guy.
And listen.
I can be deeply irritated by a man and still acknowledge greatness.
Because the Declaration?
Straight bars. I can’t even front.
AND YET.
This is also the same man who wrote “all men are created equal” while actively participating in slavery.
And if you’re already gearing up to say, “Well actually, Jefferson originally included language criticizing the slave trade—”
I know.
And yes, I know that section was removed.
That does not magically absolve him.
Because opposing the expansion of a system while continuing to personally benefit from it is not exactly the moral slam dunk some folks think it is.
But I digress……
The Declaration launched Jefferson into national prominence, but revolutionary leadership turned out to be a lot messier than writing soaring prose.
As governor of Virginia during the Revolutionary War, Jefferson had to actually govern under the pressure of British military threats, invasions, and the general chaos of war. And spoiler alert: writing eloquent ideals and managing wartime chaos are two VERY different skill sets.
When British forces advanced on Richmond, the state government fled the capital. Later, Jefferson himself narrowly avoided capture when British troops came toward Charlottesville.
Critics accused him of responding too slowly, failing to organize Virginia’s defense effectively, or simply not showing the kind of decisive leadership the moment demanded.
Whether all of that criticism was fair is debatable.
What’s less debatable is that this is another example of something we’re already starting to see with Jefferson: criticism stuck with him.
That wartime experience also shaped how he thought about executive power.
Because for all Jefferson’s later talk about limited government, actually governing through crisis taught him something different:
Sometimes emergencies move faster than the rules do.
Just tuck that away.
We’ll absolutely be coming back to it.
Then, because this man collects careers the way I collect books and board games, Jefferson reinvented himself again.
This time: diplomat.
As Minister to France, Jefferson got a front row seat to European politics, culture, and society.
Which, given his love of books, architecture, art, food, wine, and generally Fancy Things™, sounds like his version of Disney World.
And yet.
I don’t think it humbled him. I think it made him worse. 😂
Because rather than coming home dazzled by Europe, Jefferson seems to have come back even more convinced that America could — and should — do things better.
The Secretary of State
George Washington chose Jefferson to be Secretary of State before Jefferson had even fully arrived and gotten settled.
Which tells you two things immediately:
- Jefferson’s reputation was already THAT strong.
- Washington apparently loved collecting deeply opinionated men and then acting surprised when they fought. 🙃
Jefferson arrived in New York expecting to help shape a republic.
Instead, he was immediately unsettled by how many people seemed a little too comfortable with monarchical vibes.
Which makes sense.
These people had JUST fought a war to get away from a king, and now some of them were talking about executive power, ceremony, titles, and centralized authority in ways that made Jefferson look at everyone sideways.
And if Adams was extra about titles, Hamilton was extra about… basically everything else.4Read my Adams post for more on that.
Enter: Alexander Hamilton.
Now listen.
Before the Hamilton stans warm up in my comments, let me be clear:
I LOVE Hamilton. Top 3 favorite musicals of all time.
Every time he pops up in one of these biographies, I can’t help but get to singing.
Now that being said…
Lin-Manuel Miranda CAPED for that man in a way that would make you think he personally founded America while everybody else was just wandering around in powdered wigs and white stockings.
And after writing my Adams post? I still haven’t forgiven how dirty that musical did my guy.
But ANYWAYS.
Yes, Hamilton was undeniably brilliant.
But he and Jefferson looked at America and saw two completely different futures.
Hamilton wanted a strong central government. A national bank. Industry. Commerce. Manufacturing. A country that looked economically powerful and internationally respected.
Jefferson wanted a nation of independent farmers, more local control, less centralized power, and significantly less financial wizardry happening behind the scenes.
And these two men could not STAND each other.
That hateration was:
Mutual.
Immediate.
Sustained.
Professional irritation.
And because history has jokes, those same two men have become inextricably linked together because of The Room Where It Happened.
Jefferson hosted a dinner where Hamilton and Madison worked out a political compromise: Hamilton got the federal government to assume state debts, and in exchange, the future capital would be placed further South.
Which is how we eventually got Washington, D.C.
Unfortunately, the dinner solved exactly one problem.
Because Jefferson and Hamilton’s relationship only got worse from there.
And this is where Jefferson starts to make my blood pressure rise.
Because for someone who hated public confrontation and cared so much about appearances, this man stayed involved in some EXTREMELY messy political maneuvering.
His preferred methods?
Private letters.
Quiet persuasion.
Behind-the-scenes influence.
And I kept cracking up because it was the same cycle. Every. Single. Time.
Jefferson would write something spicy in private.
That private letter would inevitably become public.
People would react accordingly, suddenly side-eyeing his whole meek and mild routine.
And then Jefferson would clutch his pearls and act scandalized.
At one point, Jefferson became so frustrated with Hamilton that he wrote Madison a full emotional vent session explaining why he wanted out.
Madison — who increasingly becomes Jefferson’s emotional support statesman — tried to calm him down.
Jefferson was not interested.
He wrote:
“The motion of my blood no longer keeps time with the tumult of the world.”
Dramatic? Yes. But what else would you expect of an Aries.5 No offense! Both of my kids are Aries.
He claimed he wanted peace.
Family.
Books.
Farm life.
Retirement.
And who knows?
He probably meant it.
In the moment.
But I also think Jefferson liked influence far too much to stay away for long.
Because when he first tried to resign, Washington basically hit him with:
“Absolutely not.”
Okay, not literally.
But close.
Washington was already considering retirement himself, and both men stepping away at once would have made the young government look hella unstable.
So Jefferson stayed longer.
And while he did eventually resign in 1793 and retreat back to Monticello, political retirement for Jefferson always seems to come with an asterisk.
Because somehow, even while supposedly absorbed in peaceful rural life, he stayed deeply aware of national events.
Concerned.
Opinionated.
Writing letters.
So when Washington announced he wouldn’t seek a third term?
Jefferson’s name immediately entered the conversation.
And in one of Jefferson’s more relatable moments, he told Madison he would actually prefer coming in second and becoming vice president instead of being president.
Seems his time as Governor had really cured him of any desire to be the one in charge.
The Vice President
In the end, Jefferson got exactly what he said he wanted.
Second place.
Which, at the time, meant vice president.
And he seemed genuinely relieved.
A few months in, Jefferson described the vice presidency as “honorable and easy,” while calling the presidency “but a splendid misery.”
Given what we covered in the Adams post about the vice presidency being little more than a ceremonial waiting room, that tracks.
The job was largely presiding over the Senate, staying out of the way, and existing in case something happened to the president.
And for a man who seemed thoroughly cured of executive ambition by his time as Governor?
Sounds ideal.
Jefferson enjoyed the role.
Minimal stress.
Some influence.
No one asking him to fend off British troops.
Perfect.
Except.
Remember how Jefferson kept seeing monarchical boogeymen everywhere?
Yeah, that didn’t stop.
Even before taking office, he had written that American politics seemed to be splitting between people who genuinely loved republican government and those with what he described as “Anglican, monarchical and aristocratical” tendencies.
And because Jefferson’s personal letters apparently had all the privacy protections of a leaked group chat, THAT became public too.
Which immediately gave Hamilton’s allies fresh ammunition.
Now Jefferson was being painted as some kind of pro-French radical secretly opposed to the government he was literally serving in.
And at this point?
WHO is the leak?!
Because this keeps happening.
Hand-deliver the letters.
Use code.
Choose your confidants better.
Do SOMETHING.
What makes this stretch especially frustrating is that Jefferson and Adams actually had more alignment than either of them seemed to realize.
By this point, Jefferson had Hamilton so thoroughly living rent-free in his head that he seems to have started assuming Adams was basically operating from the same playbook.
And because the friendship between Adams and Jefferson had deteriorated, neither man was really communicating directly enough to correct those assumptions.
Which is a shame.
Because imagine an actual strong partnership between President Adams and Vice President Jefferson.
Adams’s bluntness.
Jefferson’s strategy.
Shared skepticism of Hamilton.
We’ll never know what could’ve been.
Instead?
Jefferson mostly stayed passive.
Until he didn’t.
Because then came the Alien & Sedition Acts.
And suddenly the easy, honorable vice presidency got a lot less cute.
Jefferson believed the federal government had overreached in a major way.
Not just politically. Constitutionally.
Now, I know some people hear Jefferson talking about states’ rights and immediately jump to the Civil War. But that’s not quite what was happening here.
Jefferson was not out here rooting for the country to break apart.
If anything, keeping this whole fragile American experiment together mattered deeply to him — even when that meant tolerating contradictions I have MANY thoughts about.6EveryoneknowswhatI’mtalkingabouthereright Weallknowwhat’sgoingonhere.
What Jefferson did believe was that if the federal government exceeded its constitutional authority, states had the right to push back.
Hard.
He believed limited government did not mean weak government.
It meant constrained government.
And elections, in his mind, were how the people corrected leaders who overstepped.
So by the end of Adams’s presidency, Jefferson was no longer content to sit quietly in the Senate and observe.
He was ready to fight politically.
Which means our quiet, bookish, allegedly retirement-loving friend was about to become president.
The President
The Peaceful Transfer
If Washington created the precedent of peacefully giving up power, Jefferson helped create the precedent of peacefully taking it.
And that mattered.
Because the election of 1800 was a MESS.
Deeply partisan.
Bitter.
Chaotic.
And thanks to an electoral system that was, at the time, being held together with duct tape and questionable design choices, Jefferson and Aaron Burr ended up tied.
Same party.
Same number of electoral votes.
Absolute nonsense.
Which kicked the decision to the House of Representatives.
And in one of history’s messier ironies, Alexander Hamilton helped tip the scales in Jefferson’s favor.
Not because he liked Jefferson.
Please. 😂
But because he distrusted Aaron Burr even more.
So Jefferson became president.
And in doing so, the country pulled off something genuinely remarkable:
A peaceful transfer of power between opposing political factions.
For all the accusations, newspaper warfare, political scheming, and general chaos, the government held.
Even if Adams did leave Jefferson a little parting gift.
Because in his final days in office, Adams and the Federalists rushed to fill a bunch of new judicial positions — what became known as the midnight appointments.
Which meant Jefferson walked into office already dealing with a judiciary stacked with Federalists.
And if you know anything about Jefferson by now?
You know he took that personally.
One of those last-minute appointees, William Marbury, never got his official paperwork before Adams left office.
So Jefferson basically looked at the situation and said:
He instructed James Madison not to deliver the appointment.
Marbury sued.
And then Chief Justice John Marshall — a Federalist, because OF COURSE — used the whole mess to pull off one of the greatest legal Uno reverse cards in American history.
The Court essentially said:
Yes, Marbury got played.
But also?
The Supreme Court can’t actually fix this because the law giving them that power was unconstitutional.
Which sounds boring until you realize what Marshall had actually done:
He had just established judicial review.
Meaning the Supreme Court could decide whether laws — and, by extension, government actions — violated the Constitution.
So Jefferson tried to block one Federalist appointment…
…and accidentally helped cement one of the judiciary’s biggest powers.
Incredible.
The Jeffersonian Vision
Jefferson came into office basically asking everybody to go touch grass.
Which, after the chaos of the 1790s, was probably appreciated.
His inaugural message was all about unity.
Or at least the appearance of it.
This is where he gave us the famous line:
“We are all Republicans, we are all Federalists.”
Which was basically Jefferson saying:
Can everybody PLEASE calm all the way down?
Because the previous decade had been politically exhausting.
Federalists and Democratic-Republicans had spent years accusing each other of trying to destroy the country, betray the Revolution, or secretly crown somebody king.
So Jefferson publicly positioned himself as a healer. A reset.
Less chaos. Less drama. Less government overreach.
At least in theory.
Jefferson genuinely believed the federal government should be smaller, simpler, and less intrusive in people’s daily lives.
He cut military spending.
Reduced the national debt.
Scaled back some federal operations.
And generally tried to present himself as the anti-Federalist antidote to Hamilton’s whole build-a-government-so-powerful-it-needs-its-own soundtrack energy.
Even his personal style reflected this.
Jefferson intentionally rejected some of the ceremony and pomp that had surrounded the presidency.
No extra formal nonsense.
No pretending the president was America’s slightly less British king.
This is the man who walked to his own inauguration instead of arriving in some grand display and preferred a noticeably simpler public presentation than his predecessors.
Very much giving:
“I am but a humble public servant.”
Which, given how much monarchical vibes bothered him from jump, tracks.
And one thing Jefferson did quietly shape that we still see today?
The State of the Union.
Well… sort of.
Washington and Adams had delivered formal speeches directly to Congress, very much in the style of a monarch addressing Parliament.
Jefferson looked at that setup and said:
Absolutely not.
Because of COURSE he did.
Too formal.
Too ceremonial.
Too monarchical.
So instead, Jefferson sent his annual message to Congress in writing.
A much less theatrical, much more “here are my thoughts, please read at your convenience” approach.
And that written tradition stuck for over a century until Woodrow Wilson brought back the in-person speech.
So yes.
Jefferson basically created the State of the Union as an annual presidential tradition.
He just made it significantly less awkward and significantly more introvert-coded.
He also ran his administration differently than Washington or Adams.
Washington had managed his cabinet more like a respected referee.
Adams…well, Adams basically inherited a cabinet that often acted like Hamilton still worked there.
Jefferson wanted alignment.
And by alignment, I mean people who largely agreed with him.
Which meant Jefferson’s presidency was generally less about open ideological debate and more about coordinated execution.
Less “spirited debate among equals.”
More “let’s all get on the same page.”
And because Jefferson preferred influence that was thoughtful, strategic, and a little less loud than Adams or Hamilton, this worked pretty well for him.
At first.
Because then opportunity came knocking.
And Thomas Jefferson — champion of limited government, constitutional restraint, and strict interpretation — opened the door WIDE.
The Louisiana Purchase Problem
The Louisiana Purchase is considered one of Jefferson’s greatest achievements. So why am I calling it a Problem? Well, before we talk about Jefferson doubling the size of the United States, we need to zoom out.
Because the Louisiana Purchase story does not start in Louisiana.
It starts in Haiti.
Or, at the time, Saint-Domingue.
And if your history classes mostly skipped over the Haitian Revolution?
That feels… on brand. 🙃
Because what happened there was world-shifting.
Enslaved Black people in Saint-Domingue rose up, fought back, and launched the only successful large-scale slave revolt in modern history.
Let me say that again because it deserves the emphasis:
Enslaved people overthrew the system that enslaved them. Successfully.
And European powers LOST THEIR MINDS. Napoleon, in particular.
Saint-Domingue was supposed to be the crown jewel of Napoleon’s colonial ambitions in the Americas — enormously profitable because of its sugar economy, built on enslaved labor.
Louisiana’s role was supposed to help support Saint-Domingue — providing food, raw materials, and strategic territory to help keep France’s broader colonial project running.
But the Haitian Revolution had other plans.
Toussaint Louverture.
Jean-Jacques Dessalines.
Black revolutionaries who had no intention of quietly returning to bondage.
France sent troops.
Disease wrecked them.
Resistance wrecked them.
Reality wrecked them.
And eventually Napoleon basically looked around and said:
“Well. This is going terribly.”
So he abandoned his larger North American plans.
Which is what opened the door for Jefferson.
Because once Saint-Domingue was no longer going to function as France’s colonial prize, Louisiana became significantly less useful.
And suddenly, Napoleon was willing to sell.
On the cheap.
So yes, Jefferson deserves credit for recognizing an extraordinary opportunity.
But that opportunity existed in large part because Black revolutionaries in Haiti had completely altered the geopolitical landscape.
Now, back to Jefferson.
In 1803, Napoleon offered Jefferson the chance to buy Louisiana.
And when I say Louisiana, I do not mean the state.
I mean an absolutely MASSIVE chunk of land that would double the size of the United States.
For $15 million.
Which is a WILD price for that much land.
There was just one tiny problem.
Jefferson had spent YEARS being the guy preaching strict constitutional interpretation.
And nowhere did the Constitution explicitly say:
“Presidents can absolutely buy half a continent.”
Jefferson was not dumb. He knew this.
He actually considered pursuing a constitutional amendment first.
Because yes, at least initially, his principles were PRINCIPLING.
But Napoleon’s offer came with some urgency.
And Jefferson quickly decided this was one of those moments where his constitutional rigidity needed… flexibility.
He pulled a full-body ideological stretch.
Suddenly, one of the loudest champions of limited government discovered nuance the second territorial expansion was on the table.
And while Americans celebrated opportunity, expansion, and national growth…
It’s also worth asking:
Opportunity for whom?
Because this was never empty land.
And that question is about to matter A LOT.
Expansion for Whom?
So.
About that “opportunity.”
Because yes, the Louisiana Purchase was strategically brilliant.
No one’s arguing that.
But strategic for WHOM?
Because if American history has taught us anything, it’s that when White men start talking excitedly about “opportunity” and “new land,” it is worth immediately asking:
New for who? Who already lives there?
And in this case? The answer is A LOT of people.
The Louisiana Territory was home to dozens of Indigenous nations with their own governments, economies, trade systems, cultures, alliances, and histories.
But American expansion narratives have a nasty habit of treating land as empty the moment White Americans decide they want it.
Jefferson was no exception.
Now, to be clear, Jefferson was genuinely fascinated by exploration, science, geography, plants, animals, and collecting information.
This is VERY on-brand for our resident nerd.
So yes, the Lewis and Clark expedition was partly about scientific discovery.
Mapping.
Cataloguing species.
Learning about terrain.
All very exciting if you’re into that sort of thing.
But let’s not pretend that was the whole story.
Because expeditions like that also served a very practical political purpose:
Figure out what was out there.
Who was out there.
And how the United States could extend control over both.
Jefferson’s vision for westward expansion was not neutral curiosity.
It was nation-building.
Empire-building, if we’re being honest.
And Jefferson did have ideas about what should happen to Indigenous nations.
Spoiler alert:
They were not “leave them alone.”
Jefferson’s preferred approach, at least initially, was what we’d now call forced assimilation.
He believed Indigenous people could be “civilized” — meaning pushed toward European-American farming practices, Christianity, debt dependency, and cultural abandonment.
Because naturally, when men like Jefferson said “civilization,” they mostly meant:
“Become more like us.”
And if Indigenous nations resisted?
Well.
Then removal started looking more acceptable.
So while Andrew Jackson gets the big public villain role in most conversations about Indigenous people removal — and trust, we will GET there7 LORD, I hate that man — some of the ideological groundwork was already being laid much earlier.
Including here.
Under Jefferson.
Which makes the contradiction especially sharp.
Because the man who wrote passionately about liberty was also laying groundwork for dispossession.
The man who distrusted concentrated power was perfectly comfortable expanding national control over lands already inhabited by sovereign peoples.
The man who loved freedom was very selective about whose freedom counted.
And I know.
Some people will say:
“Well, that’s just how people thought back then.”
To which I would say:
Not ALL people.
And even if many did, widespread harm does not magically become morally neutral because it was popular.
So yes.
The Louisiana Purchase was brilliant.
And yes.
It dramatically changed the trajectory of the United States.
But brilliance and violence have never been mutually exclusive in American history.
And Jefferson, once again, contains both.
Burr (Again 🙄)
And because Jefferson’s presidency apparently refused to be normal, we have to talk about Aaron Burr.
Again.
Now, if you somehow don’t know who Aaron Burr is, here’s the quick version:
He was Jefferson’s vice president.
Ambitious.
Deeply opportunistic.
And apparently made everyone around him nervous.
Including Hamilton.
Which, to be fair, says something, because Hamilton himself was not exactly the poster child for emotional stability.
Y’all between the Adams post and this one, I’m starting to feel like Hamilton and Burr deserved one another.
Now, if you recall, Burr originally tied Jefferson in the election of 1800, sending the whole mess to the House.
Jefferson eventually won and Burr became vice president.
Which is already awkward enough.
Because imagine accidentally almost becoming president, losing to the guy you tied with, and then having to just… show up to work. For that same guy.
And the relationship didn’t improve over time.
Jefferson never really trusted Burr.
Burr, meanwhile, increasingly seemed like a man constantly auditioning for whatever role offered the most power.
Then, in 1804, Burr, politically damaged and increasingly isolated, got into his now-infamous duel with Alexander Hamilton.
Yes, the one from the musical. You know, where Hamilton throws away his shot?
Except in real life, less singing, more actual death.
And while part of me can acknowledge that Hamilton absolutely seemed capable of talking himself into this exact situation…
Killing a former Treasury Secretary tends to be bad for your public image.
Who would’ve thought?! 🤷🏾♀️
Jefferson, unsurprisingly, was done with Burr at that point.
Politically.
Socially.
Spiritually.
DONE.
But because Aaron Burr apparently believed “rock bottom” was just a suggestion, things somehow got weirder.
A few years later, Burr got tangled up in what may or may not have been an actual conspiracy to carve out some kind of independent empire in the western territories.
I say “may or may not” because historians still argue about what exactly this man thought he was doing.
Starting his own country?
Invading Spanish territory?
Just freelancing treason?
Pretty unclear.
Jefferson, however, was VERY clear.
He publicly treated Burr like a traitor.
Burr was arrested and tried for treason.
And in yet another ironic twist, Chief Justice John Marshall — yes, HIM again — presided over the case.
Burr was acquitted.
Because apparently Jefferson and John Marshall were destined to stay in each other’s business. I’m surprised Jefferson and Marshall didn’t end up in a duel themselves at this point.
Second Term: The Find Out Phase
Jefferson’s second term is where theory met reality.
And reality said:
Because for all of Jefferson’s brilliance as a thinker, writer, and visionary, governing an actual country in a messy global conflict turned out to be significantly harder than having strong opinions in beautifully written letters. Something he apparently hadn’t learned enough of during his time as Governor.
At the center of the mess was Britain and France.
While America was over here trying very hard to stay neutral, Britain and France were deep in the Napoleonic Wars and absolutely did not care about America’s desire to mind its own business.
American ships kept getting caught in the middle.
British forces were stopping American ships, seizing cargo, and — perhaps most infuriatingly — impressing American sailors.
Which is a polite historical word for:
kidnapping people and forcing them into military service.
Not ideal.
Then came the Chesapeake-Leopard Affair in 1807.
A British warship attacked the USS Chesapeake off the American coast, killed and wounded American sailors, and forcibly removed men they claimed were deserters.
Americans were FURIOUS.
This was exactly the kind of incident that pushes nations into war.
But Jefferson did not want war.
War is expensive.
Messy.
Unpredictable.
And we all know Jefferson does not do messy and unpredictable.
Plus, Jefferson had spent plenty of time talking about limited government and skepticism toward standing military power.
So instead of war, he chose economic pressure.
Enter: the Embargo Act.
Jefferson’s grand idea was basically:
If Britain and France want American goods and trade access so badly, we’ll just… stop trading with them.
No ships leaving American ports.
No exports.
In theory, it was pretty clever. In practice?
Reality left Jefferson saying:
“Well, well, well, if it isn’t the consequences of my own actions.”
Because the people hurt most immediately were not Britain and France.
It was Americans.
American merchants.
American sailors.
American port cities.
American businesses.
The economy was on the struggle bus.
Smuggling exploded.
People ignored the embargo.
Public frustration skyrocketed.
And suddenly Jefferson — champion of limited government — found himself needing increasingly aggressive federal enforcement to make his big federal policy actually work.
Which is… funny.
Not funny haha.
Funny interesting.
Because once again:
Jefferson’s principles got REAL flexible the second reality became inconvenient.
The man who distrusted centralized federal power suddenly needed centralized federal power.
The man who championed limited government found himself backing enforcement measures that felt… not especially limited.
Now, if we want to give grace, then yes, Jefferson was trying to avoid war. But the policy was deeply unpopular and largely ineffective.8Sound familiar? Cuz if you want to give grace to Jefferson in trying to avoid war, you better be keeping that same energy for my boy, Adams.
So instead of being remembered as Jefferson’s brilliant peacekeeping masterstroke…
the embargo mostly became remembered as economic self-sabotage.
And what feels especially Jefferson about all of this is what happened at the end.
Because when things got hard — really hard — Jefferson’s old habits kicked in.
The same retreat instinct we’ve already seen.
The same Monticello energy.
The same “I would actually prefer to be home with my books” reflex.
As the embargo unraveled, public frustration exploded, and foreign policy tensions kept escalating, Jefferson increasingly seemed to just… emotionally check out.
Not in the formal sense.
He was still president.
But in the leadership sense?
The urgency.
The clarity.
The visible direction?
Much shakier.
And it’s hard not to notice the pattern.
Jefferson loved designing systems.
Loved articulating principles.
Loved imagining what government should be.
But when governing got deeply messy, deeply unpredictable, and politically ugly?
His instinct often seemed to be retreat. He basically ghosted.
Which, unfortunately, is not an ideal presidential leadership strategy.
And with that?
Jefferson was done.
After two terms, he stepped away from the presidency and returned — where else? — to Monticello.
Because of course he did.
The man loved many things.
Books.
Architecture.
Ideas.
Influence.
A carefully curated image of retirement that somehow always seemed to include staying deeply invested in public life.
And in some ways, leaving office gave Jefferson the chance to focus even more fully on the parts of his legacy he actually wanted to shape.
Because if there is one thing Thomas Jefferson understood, it was authorship.
Not just of documents.
Of ideas.
Of institutions.
Of how history might remember him.
And some of the things he most wanted remembered had nothing to do with the presidency at all.
On Religious Freedom
For all the contradictions we’ve talked about, this is one area where Jefferson gets real flowers from me.
Because Jefferson believed deeply that the government had absolutely no business telling people what to believe about God.
Long before he became president, Jefferson helped push through the Virginia Statute for Religious Freedom — something he later considered one of the greatest accomplishments of his life.
Not the presidency.
Not the Louisiana Purchase.
THIS.
In fact, when Jefferson chose what would go on his gravestone, religious freedom made the list.
That tells you how important this was to him.
The core idea was simple but genuinely radical for the time:
Your relationship with religion — or your decision to have none at all — should not depend on whoever happens to be in political power.
Government should not be punishing people for belief.
Rewarding people for the “right” belief.
Or forcing people to financially support a religion they didn’t agree with.
This was a big deal.
And I think part of what makes this especially interesting is that Jefferson himself was… religiously complicated.
He believed in God.
He believed in morality.
He admired Jesus’s ethical teachings.
But traditional Christianity?
Not so much.
Jefferson did not believe Jesus was divine.
He rejected miracles.
Rejected the resurrection.
Rejected the supernatural parts of scripture altogether.
Which is SUCH a Thomas Jefferson move.
He basically looked at the Bible and said:
“I like parts of this. But I can edit it to make it even better.”
He created what’s now known as the Jefferson Bible — essentially removing the miraculous bits and keeping Jesus’s moral teachings.
Nerd Work.
But a deeply opinionated nerd.9Again, I hate how much I can relate to Jefferson on some points.
What fascinates me, though, is how much loss Jefferson lived through.
His wife.
Children.
Loved ones.
Repeatedly.
And I do find myself wondering what role faith played in helping him make sense of grief.
Because even though Jefferson rejected a lot of orthodox Christian doctrine, he did seem to believe in a higher power, moral order, and some version of life beyond death.
Which makes sense.
Because grief tends to make humans ask the biggest questions.
And Jefferson, if nothing else, loved a big question.
But unlike so many people throughout history, Jefferson did not think his personal beliefs should become everybody else’s rules.
And that distinction matters.
Especially now.
Because while Jefferson could be deeply frustrating, slippery, elitist, hypocritical, and maddeningly selective in applying his principles…
On religious freedom?
He was ahead of his time.
On Education
If Thomas Jefferson loved anything almost as much as Thomas Jefferson loved Thomas Jefferson’s ideas…
It was education.
And this is yet another area where I have to give him real credit.
Because Jefferson believed education was essential to democracy.
Not a nice bonus.
Essential.
He genuinely believed an uninformed public was vulnerable to manipulation, bad leadership, and tyranny.
Or, in his words:
“People are the only safe depositories of their own liberty, & they are not safe unless enlightened to a certain degree.”
I told y’all the man could WRITE.
Jefferson believed the greatest threat to liberty wasn’t ordinary people getting a little too rowdy. It was concentrated power.
Government overreach.
Political repression.
People handing too much authority to powerful leaders out of fear.
His answer?
Education.
Because in Jefferson’s mind, the best defense against tyranny was an informed public capable of thinking for themselves.
I can absolutely rock with that.
Jefferson’s vision was not exactly some egalitarian public education like most want to pretend modern American believes in today.
He believed education should help identify what he called “natural geniuses” — talented individuals whose abilities could elevate them regardless of birth or family status.10Think of something similar to The Talented Tenth.
So, who exactly got counted in this beautiful education vision was… limited.
Because as with so many Jeffersonian ideals, the theory was broader than the practice.
Still, the larger idea was important:
Knowledge should not be reserved exclusively for wealthy elites.
That was genuinely forward-thinking.
And Jefferson didn’t just talk about education.
He walked it how he talked it.
In his later years, one of his biggest obsessions became founding the University of Virginia.
Which, fittingly, was one of the accomplishments he considered most important in his entire life.
Again, not his presidency or the Louisiana Purchase.
The Declaration of Independence.
Religious freedom.
The University of Virginia.
That was HIS list.
Jefferson was deeply involved in designing UVA — not just academically, but physically.
The architecture.
The campus layout.
The whole concept.
The idea of the “academic village” — the campus as an intentional intellectual community — was part of Jefferson’s vision.
He also pushed for something unusual for the time:
No rigid required curriculum.
Students could choose areas of study.
Which feels extremely on-brand for a man who wanted to study approximately everything.
And again, I have to give credit where it’s due.
Because Jefferson wasn’t thinking about education as job training.
He saw it as democracy maintenance.
Civic development.
Moral development.
Intellectual freedom.
But because this is Thomas Jefferson, we also have to acknowledge the contradiction sitting RIGHT there.
The university he dreamed into existence?
Was built by enslaved labor.
Because apparently this man could imagine revolutionary systems of thought…
…just not freedom for everyone helping build them.
And if that doesn’t sum Jefferson up?
I don’t know what does.
On Slavery
Welp.
Here we are.
Because no conversation about Thomas Jefferson can avoid this.
Nor should it.
And before we even get into specifics, let me say this plainly:
Jefferson knew slavery was wrong. No ifs, ands, or buts about it.
That’s part of what makes this so maddening.
He called slavery morally corrosive — damaging not just to the enslaved, but to the people doing the enslaving.
He worried that systems built on domination taught people to trample the rights of others and lose their own humanity in the process.
AND THAT’S ON MARY HAD A LITTLE LAMB.
Because once you normalize violating someone else’s humanity, it changes you too.
Not only that.
It changes institutions.
Politics.
Culture.
Law.
That part of Jefferson’s analysis feels depressingly timeless.
And as a younger man, Jefferson did make attempts — limited ones — to push against parts of the institution.
- He tried to make it easier for enslaved people to be legally freed.
- He represented a mixed-race man seeking freedom.
- He included anti-slavery language in early drafts of major political documents.
- He supported ending the transatlantic slave trade.
- He even proposed gradual emancipation in some forms.
And yet.
He enslaved people his entire adult life.
Hundreds of them.
Bought them.
Sold them.
Benefited from their labor.
Built his life, comfort, and legacy on work he did not freely compensate.
And that contradiction is the story.
Because Jefferson’s opposition to slavery was almost always theoretical.
Gradual.
Deferred.
Somebody else’s problem.
Future tense.
Never urgent.
Never fully personal.
Because it is one thing to say slavery is evil.
It is another thing entirely to free the people currently enslaved by YOU.
Jefferson rarely made that leap.
And yes, defenders will point to the complexity.
His crushing debt.
Virginia law.
Financial constraints.
The fear that emancipated people could be re-enslaved to satisfy creditors.
The practical barriers.
And some of that is real. Because one thing I know to be true is that human beings are walking contradictions. It’s easy to rant about the past as if people back then were uniquely hypocritical, as though humans haven’t always been capable of saying one thing and doing another. History just gives us some particularly high-stakes examples.
But.
Jefferson was also incredibly resourceful when pursuing the things he actually prioritized.
Education?
Religious liberty?
Territorial expansion?
Architecture?
Books?
Political influence?
He found ways.
So when it came to slavery, the question becomes less could he imagine alternatives?
And more:
Why was urgency always missing?
Part of the answer is simple but deeply ugly.
Jefferson didn’t believe in racial equality.
In Notes on the State of Virginia, he repeated racist ideas about Black inferiority — intellectually, emotionally, socially.
He could recognize slavery as morally wrong while still believing Black people were fundamentally different and unequal.
Which is a contradiction, yes. But unfortunately not a rare one.
Enter: Benjamin Banneker.
Because history occasionally gifts us moments where somebody says exactly what needed to be said.
Banneker was a free Black mathematician, astronomer, surveyor, almanac author, and all-around intellectual powerhouse who wrote Jefferson directly in 1791.
That letter went something like:
Dear Sir:
You wrote “all men are created equal.”
You clearly understand oppression, given all that energy about Britain violating colonial rights.
You seem capable of recognizing injustice.
And here I am. Living, breathing evidence that your little Black inferiority theories are looking shaky — at best.
Sooooo…
what exactly are you planning to do about slavery and racial prejudice?
(Paraphrasing. But honestly? Not by much.)
And Jefferson actually wrote back.
He praised Banneker’s accomplishments.
Acknowledged his intellect.
Talked about wanting to see more evidence disproving racist assumptions about Black intellectual inferiority.
Even shared Banneker’s almanac with folks in Europe.
And Banneker and his supporters understandably took that letter like:
SEE?! EVEN THOMAS JEFFERSON SAID IT.
Except…
Once again, Jefferson’s letters stayed leaking like your grandma’s church roof after the pastor done asked for a special offering every Sunday since 1998.
Because once that response started circulating publicly?
Here came the side-eyes.
And from what we can tell, some of Jefferson’s White peers were coming to him like:
So let me get this straight.
A Black man challenged you directly.
You complimented him publicly.
And now people are using YOUR words to argue against racist assumptions and slavery?
And Jefferson?
SO sensitive about his public image.
SO unwilling to sit comfortably in controversy.
SO committed to preserving his own standing.
That instead of standing ten toes down in what he had written?
He backpedaled.
Later, Jefferson became dismissive of Banneker’s abilities, skeptical of how original his work actually was, and generally started retreating from the very openness he had initially shown.
From what I can see? Straight-up coward behavior.
Because even when presented with direct evidence that challenged his worldview, Jefferson chose his comfort over courage.
Again.
And even his preferred “solutions” reflected that worldview.
Jefferson did not envision a thriving multiracial democracy.
He envisioned emancipation paired with removal.
Colonization.
Separation.
Sending freed Black people elsewhere because he believed coexistence would inevitably end in racial violence.
And listen… he wasn’t wrong that a nation built on slavery was planting the seeds for racial violence.
But, the fact that he could imagine a nation founded on revolution but not a multiracial society says A LOT.
Because at some point, “I can’t imagine it” stops being analysis and starts being moral failure.
And then there’s the intimacy of the contradiction.
Because while Jefferson publicly theorized about racial separation, his own household was the living contradiction of those beliefs.
And yes, I am talking about Sally Hemings.
I’m making a very intentional choice not to fully unpack that relationship here.
Not because it’s unimportant.
Quite the opposite.
It is so important — and so layered — that it deserves its own dedicated post.
Actually, it deserves better than me trying to squeeze it into an already too-long Jefferson post between the Louisiana Purchase and Aaron Burr freelancing treason.
So this feels like the right time to introduce a new part of this project:
Side Quests
Because while this series is centered on U.S. presidents, there are too many other people orbiting these stories who deserve deeper attention.
Sally Hemings, absolutely.
Benjamin Banneker, because the man was out here challenging Thomas Jefferson directly with receipts.
Alexander Hamilton, because clearly that man refuses to stay out of anybody’s narrative.
Aaron Burr, because WHAT was going on there?
Benjamin Franklin, because I already have questions.
And probably others as we go.
But Sally Hemings especially.
Because too often she gets reduced to a sidebar in Jefferson’s story.
And I am not interested in doing that.
She was a real person.
An enslaved woman.
A member of the Hemings family.
A woman whose life existed within a deeply unequal power structure.
A woman whose story deserves to be centered on its own terms, not merely as an extension of Jefferson’s biography.
So before I write that post, I’m planning to read The Hemingses of Monticello by Annette Gordon-Reed.
And yes, I am being intentional about reading a Black woman historian on this subject.
Because who tells history matters.
Whose perspectives have been centered matters too.
And because if I’m going to engage that story, I want to do it thoughtfully.
So for now, I’m naming the contradiction without pretending I’ve done the deeper work yet.
Because the contradiction is UNBEARABLY OBVIOUS.
And perhaps what frustrates me most is this:
Jefferson kept waiting.
Waiting for better timing.
Waiting for future generations.
Waiting for systems to evolve.
Waiting for Providence.
Waiting for literally anyone else to solve it.
And in that waiting, real people remained enslaved.
People with names.
Families.
Skills.
Dreams.
Trauma.
Lives.
Including the people who built and maintained Monticello.
The people who made his lifestyle possible.
The people whose labor supported the very intellectual freedom he so loved.
So when people call Jefferson an “antislavery slave owner,” I understand what they mean.
But I also think that phrase is eye-rolling levels of basic.
Because if your opposition to injustice never meaningfully disrupts your own participation in it…
what exactly are we measuring?
Jefferson did more than some of his peers in rhetoric.
Less than morality demanded in practice.
Who Gets to Tell the Story?
I want to zoom out for a second.
Because this section is not really about Jefferson.
Not entirely.
It’s about history.
And who gets to shape the stories we inherit.
For this post, I read Jefferson: Architect of American Liberty by historian John B. Boles.
The book was fascinating.
Not just because of Jefferson.
But because it became an accidental case study in how historians grapple with the collapse of long-protected narratives.
Because for YEARS, historians had wiggle room when it came to Sally Hemings.
The relationship could be minimized.
Questioned.
Doubted.
Dismissed.
Filed away under:
“Well, we just don’t know.”
And then science entered the chat.
DNA evidence made the long-standing denials much harder to sustain.
Suddenly, the question was no longer whether the Jefferson family line was connected to Sally Hemings’s children.
So historians had a choice:
Reckon honestly with what that meant.
Or…
start doing narrative gymnastics.
And BABY.
Some of this book had me watching Olympic-level routines.
Because the number of explanations offered to soften, contextualize, rationalize, or otherwise emotionally pad Jefferson’s relationship with an enslaved woman under his power?
WHEW.
At one point, Boles references an 18th-century Swiss medical writer whose truly bizarre theories suggested scholarly men could suffer intellectual exhaustion from retained seminal fluid.
Yes.
That is a sentence I had to read with my own two eyes.
And from there, the speculation becomes:
Well perhaps Jefferson believed intimacy with Sally was somehow medically beneficial.
…
Be so for real right now.
Because THIS is what I mean when I say we have to think critically about how history gets written.
There’s a difference between:
“Here is what the historical record supports.”
And:
“Here is a thing I, the historian, have speculated might explain behavior.”
Those are not the same.
But if you’re reading nonfiction casually — and understandably assuming the author is grounding claims in solid evidence — those distinctions can blur FAST.
A historian’s “well, maybe…” starts getting repeated like established fact.
That conclusion gets repeated enough.
And suddenly?
Congratulations.
We have lore.
This happens all the time in history.
And to be clear, interpretation is part of historical work.
Historians are constantly piecing together incomplete records, context, motives, and probabilities.
That’s not inherently the problem.
The problem is when speculation gets treated like neutral fact.
Or when interpretation consistently bends toward preserving the dignity of already-powerful people.
Because let’s be honest.
Who usually gets that level of narrative generosity?
And that’s what made this book such a wild reading experience for me.
Because here we have a historian clearly trying to reckon with newer realities that disrupt a long-standing heroic narrative…
while still seeming emotionally committed to preserving Jefferson’s stature.
Which kept reminding me that history is never just about the past.
It’s also about the people telling the story.
What they value.
What they excuse.
What they emphasize.
What they quietly soften.
And that changes how you read everything.
Because I cannot pretend I read this book from some detached place of pure neutrality either.
I don’t.
Nobody does.
We all bring perspective.
Questions.
Experiences.
Biases.
Assumptions.
That includes historians.
It’s never just been about what stories get told, but who gets to tell them.
Because for a very long time, many of these narratives were shaped overwhelmingly by people invested — consciously or not — in preserving certain kinds of Great Man mythology.
And once you start seeing that?
You can’t unsee it.
Which doesn’t mean Jefferson wasn’t brilliant.
He was.
It doesn’t mean his accomplishments disappear.
They don’t.
It means brilliance does not exempt anyone from scrutiny.
And genius should never become a shield against honest historical reckoning.
The Legacy
Thomas Jefferson didn’t just shape America.
In a lot of ways, he is America.
And I mean that as both compliment and indictment.
Because how do you even sum up a man like this?
A brilliant writer. A revolutionary thinker. A champion of democracy, religious liberty, and education. A man whose ideas helped shape the very language Americans still use when talking about freedom.
And also:
An enslaver. A racial elitist. A man capable of extraordinary moral clarity in theory and staggering moral failure in practice.
It’s a lot.
And maybe that’s part of why Jefferson has fascinated people for so long.
Unlike someone like Washington, whose reputation has been pretty neatly packaged for public consumption, Jefferson feels much slipperier.
There’s a reason he became known as The American Sphinx.
The man literally burned his correspondence with his wife Martha, which feels deeply rude to historians and incredibly on brand.
Jefferson seems to have believed some parts of himself belonged only to him. The future could have his ideas, his institutions, and his political philosophy. His inner life? Not so much.
And that silence probably made the mythmaking easier.
Because people are very good at filling in gaps with projection.
What Jefferson leaves us with is enough brilliance for people to build monuments around his legacy and enough contradiction for those monuments to crack under scrutiny.
Because his fingerprints are everywhere.
The Declaration of Independence.
Religious liberty.
Public education.
The University of Virginia.
Doubling the size of the country.
The idea that democracy requires an informed public.
Even debates we’re still having about constitutional interpretation, executive power, federal authority, and the meaning of liberty carry Jefferson’s fingerprints.
Even his contradictions feel distinctly American.
One thing that kept hitting me while reading this biography was how familiar some of this felt.
Peaceful organizing.
Resistance to oppressive power.
Arguments about liberty.
Disagreements over whose rights actually count.
Who gets protected and who gets punished.
Different context. Different stakes. But recognizable rhythms.
Because revolutions may change their clothes, but some patterns stick around.
I also kept thinking about how incredibly small this political world was.
The same names.
The same rivalries.
The same men rotating through power, writing letters, arguing, becoming presidents, and reshaping the country in real time.
It reminded me of The President’s Club—that strange fraternity of people who shared an experience almost no one else could fully understand.
Except here, they were inventing the presidency while actively figuring out what it meant.
And Jefferson’s greatest strength may also have been one of his greatest weaknesses.
The man was exceptional at ideas.
Philosophy.
Argument.
Political theory.
Systems.
Vision.
Execution was shakier.
Because when Jefferson was writing principles, he was operating at an elite level.
When Jefferson had to apply those principles in messy real-world situations?
Results varied.
See:
Virginia governorship.
The embargo.
Slavery.
For all his contradictions, though, Jefferson did understand something fundamental about democracy: it cannot remain frozen.
This is one area where I think he was genuinely ahead of his time.
Jefferson rejected the idea that the Constitution should be treated as sacred, untouchable text incapable of revision. As he wrote:
“Some men look at constitutions with sanctimonious reverence…”
Which is a wildly modern sentiment coming from a Founder.
In Jefferson’s view, a nation should grow and evolve, and its laws should change alongside it.
And then, you have to look at the end of his journey.
Because for all his brilliance, Jefferson died deeply in debt.
There were even efforts, including a lottery, to help address his finances.
Which feels like such an oddly human ending for someone of his stature.
But maybe it fits.
Because Jefferson’s life resists clean endings.
Even his gravestone tells you exactly how he wanted to be remembered.
Author of the Declaration of Independence.
Author of the Virginia Statute for Religious Freedom.
Father of the University of Virginia.
That list makes perfect sense.
Jefferson never really saw himself as an executive first.
He saw himself as an architect.
Of ideas.
Of institutions.
Of national identity.
The problem is that the people designing systems are not always the ones forced to live with the consequences.
And Jefferson built some extraordinary things.
While also helping preserve some devastating ones.
That, to me, is the legacy.
Random, Interesting Facts
Even though this post is already aggressively long, y’all know I can’t resist this section.
So let’s end with some historical tea.
First: Jefferson was messy too.
And at this point, I’m left wondering: which Founding Father isn’t?!
Jefferson had longtime family friends, Peter and Elizabeth (Betsy) Walker.
At some point while Peter was away, Jefferson apparently decided this was the perfect time to make an inappropriate advance toward Betsy.
Now, what exactly happened is unclear.
But whatever happened was significant enough that years later, Betsy told her husband.
And THEN, because apparently men in this era processed emotions on a 15–20 business year delay, Peter eventually confronted Jefferson and started making duel noises.
Intermediaries stepped in before anybody started dramatically measuring pistol distance at dawn.
And Jefferson later admitted:
“When young and single, I offered love to a handsome lady. I acknowledge its incorrectness.”
Well. That’s one way of putting it.
Second: Jefferson was an architecture nerd.
As with everything else, Jefferson looked around Europe and said:
Because Jefferson absolutely fell in love with European architecture — and then spent a good chunk of his life remixing those ideas for America.
Monticello is probably the clearest example of this.
That house was basically Jefferson’s lifelong architectural obsession project.
He kept redesigning it.
Tweaking it.
Reimagining it.
Because apparently even his HOUSE had to reflect his personal brand.
But his influence went way beyond Monticello.
Jefferson helped popularize the classical temple-style architecture that ended up shaping the look of American public buildings.
So, the next time you’re in DC, looking at all those columns and domes and such? You can attribute that to Jefferson and his “democracy but make it Roman Empire” aesthetic.
Third: Jefferson the Spy?
Jefferson apparently just casually developed a cipher code system that later influenced American military cryptography.
There’s no evidence he personally used it.
But the fact that he just casually invented encryption tools anyway?
Big Nerd Energy.
Fourth: Fellow data nerds, unite!
Jefferson took the national census seriously as a tool for understanding the shape, growth, and makeup of the country.
Which means every time we all collectively complain about census forms but take it anyway for good survey karma?
We can thank (blame?) Jefferson.
Fifth: he also helped create West Point.
Because apparently Jefferson was collecting side quests like my kids collect Pokémon cards.11But don’t ask me nothing about it because I refuse to learn.
The U.S. Military Academy at West Point was established during his presidency in 1802.
So we have:
Book nerd.
Architecture nerd.
Democracy nerd.
Military infrastructure nerd.
The range is crazy.
And finally: this man almost died in the most ridiculous way imaginable.
A sculptor was making a life mask of Jefferson by pouring plaster over his face.
Which already sounds like the beginning of a terrible idea.
And then it GOT WORSE.
The plaster hardened too quickly.
Jefferson couldn’t breathe.
Couldn’t call for help.
Was getting weaker by the second.
And in what feels like a dramatic movie moment, he managed to slam a nearby chair to the floor to get attention.
And who came to save him?
His enslaved valet, Burwell Colbert.12Black people saving the day ONCE AGAIN.
Burwell rushed in and started trying to break the plaster off while the sculptor finally joined the rescue effort.
And Jefferson survived.
Like… can you imagine? After everything, THAT’S how Thomas Jefferson goes out?
The Rankings
Quick reminder on how this works:
Fave Ranking: Plain and simple — ranking presidents based on who I personally like the most to who I absolutely cannot stand.
Presidential Ranking: Did you actually do what you set out to do? Did you president effectively?
Impact Ranking: How big is your footprint on the DNA of America?
Now.
As for Jefferson…
Fave Ranking: #2
Okay, so we’re only three presidents in, which means this hasn’t gotten that tricky yet.
But let me be clear:
Jefferson was never beating Adams.
Y’all should’ve known that.
Adams is my guy.
Jefferson is brilliant. One of the greatest thinkers and writers we’ve ever produced.
But also?
That fake polite thing he did in public while writing absolute FIRE in private letters would irritate the HELL out of me.13See what I did there? Fire? Hell? 🤣
Like pick a lane.
Actually no.
Don’t.
Because I absolutely would want front-row access to those leaked letters.
The gossip?
Immaculate.
The drama?
Elite.
Me wanting all the tea while refusing to personally be involved in any of it feels like peak Gemini behavior.
So yes, Jefferson gets second place.
Because while Washington is objectively important…
That man is kind of boring to me.
America’s first action hero.
And I’m more of a sci-fi girl.
Presidential Ranking: #2
Now THIS is where I reverse course a bit, even though the ranking stays the same.
Because Washington’s primary job was basically:
Keep this experimental little country from immediately falling apart.
I mean… how do you top that?
You don’t.
Washington had the impossible first assignment, and somehow pulled it off.
Jefferson, for all his brilliance, had a much messier presidential record.
Because on the one hand, you have:
The Louisiana Purchase.
West Point.
Lewis & Clark.
On the other hand, you have:
The embargo.
“Limited government unless I need big government real quick.”
And I know that game.
It’s called:
Do as I say, not as I do.
So yes.
Jefferson still lands at #2.
But firmly behind Washington here.
Impact Ranking: #2
Sorry, Adams. 😭
Because Jefferson clears Adams here too.
And honestly?
It wasn’t even close.
Jefferson’s fingerprints are ALL OVER this country.
The Declaration of Independence.
Religious freedom.
Public education.
The University of Virginia.
The Louisiana Purchase.
Constitutional interpretation debates.
Executive power debates.
States’ rights debates.
Even the contradictions baked directly into American democracy itself.
And, I mean…
The man is literally on Mount Rushmore.
So yeah.
Jefferson gets second here too.
Pour one out for my homie Adams, whose impact was enormous but just doesn’t loom over the American imagination in quite the same way.
But now I need to hear from y’all. How would you rank the presidents so far? Agree? Disagree? Think my Adams bias has completely compromised my objectivity? Fair. 😂 Drop your thoughts in the comments. And because I know this is only going to get messier as the list gets longer, I’ve officially started a Presidential Rankings page so you can keep track of where everybody stands.
And with that, we leave behind America’s slippery philosopher king.
Next up:
James Madison.
The so-called Father of the Constitution.
Short king.
Jefferson’s ride-or-die.
Occasional emotional support statesman.
And yet another man who had some VERY strong opinions about liberty while actively participating in slavery.
sigh
See y’all soon.
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