James Monroe

Haaaaaaaaaaaaaaaaaaaay!

I know, I know.

I’m sure there are some of y’all who thought I had really fallen off and wasn’t coming back.

But here I am!

Done ghosted for two whole months, but I’m here!

And I’m just going to skip all the I’m sorry’s and the “here’s what happened” and why I’m late and all that.

Let’s get right down to it.

You see that scroll bar size?

You already know what it is. 😂

Plus, this biography was only about 350 pages, yet somehow, I got 35 pages of notes out of it.

So…there’s also that.

But, I’m super excited to share this one with y’all.

Because something clicked for me while I was reading James Monroe’s biography.

By the time I finished this book, I felt like I finally understood the Revolutionary War and the early years of the United States in a way I hadn’t before.

And I swear, reading this biography was like reading the fourth gospel in the Bible.

Once you’ve heard the same story from Matthew, Mark, Luke…

and John comes along?

I CLOCKED EVERYTHING.

I recognized the people. The relationships. The political maneuvering.

Which is probably what made this post take so long.

But because it HAD been so long since the last post, I also went back and reread all of my previous posts.

And I’m going to be real with y’all.

I didn’t think my last couple of posts were me at my best.

There were times when I felt like I was just giving you facts.

Then THIS happened.

And then THIS happened.

And then THIS happened.

Ain’t that crazy?!

Here’s a GIF!

There’s a GIF!

EVERYBODY GETS A GIF!¹Now this post probably has the most gifs out of all of them, but I digress.

And I realized I wanted to get back to the whole reason I started this blog in the first place.

I wanted to humanize these larger-than-life figures.

I wanted to take these stories—which weren’t always written with people like me in mind—and translate them in a way that felt accessible, funny, and connected to how I see the world.

I wanted you and me to find some kind of connection to each other and to OUR history.

And not to toot my own horn, but I think I did that with this one.

So I’m excited to finally share it with y’all.

I hope you think it was worth the wait.

Let’s talk about The Last Founding Father: James Monroe.

James Monroe: The Timeline Edition

In case you need to get your bearings in the space-time continuum.

The Man: A Brief Bio

Sooo, stop me if you’ve heard this before.

April 28, 1758. Virginia. Planter family.

James Monroe was the second of five children and the oldest boy—which, in a family like this, basically meant he was expected to be the Little Man of the House.

His father, Spence Monroe, was warm but strict. His boys were expected to farm, fish, shoot, and generally make themselves useful.

James took the job seriously.

At 11, he was enrolled in the county’s only school, where—like other farm boys—he attended for about twelve weeks a year, squeezed in between the fall harvest and spring planting.

And then, when Monroe was 14, his mother died following the birth of her youngest child. His 19-year-old sister, Elizabeth, took over the mothering duties of the house, including caring for her younger siblings.

And then their father died too.

So at 16, James Monroe inherited the family farm and became, in every practical sense, the Big Man of the House.

He went home to manage the farm and look after his younger brothers, most of whom were too young, sick, or lazy to look after themselves.

Fortunately, Monroe had someone in his corner: his wealthy maternal uncle, Judge Joseph Jones.

We’re going to be seeing a LOT of this man, so I’m just going to call him Uncle JJ.

Uncle JJ became Monroe’s guardian, surrogate father, caretaker, and benefactor. But more importantly, he saw something in James.

First, he got him back into school.

Specifically, the College of William & Mary.

And then, most important to our story—and to the trajectory of Monroe’s life—he introduced him to politics.

He took his teenage nephew to the House of Burgesses,²Quick reminder that this was Virginia’s legislative body—like an early version of the state House of Representatives. And if you had to read this footnote, that means you either haven’t been reading my posts or haven’t read them in a while. So, go read them! where Monroe was exposed to some of Virginia’s most prominent political figures—including a young Thomas Jefferson and George Washington.

And so I just want you to take a snapshot of this.

Here we have a parentless young man whose benefactor—and father figure of an uncle—has now escorted him into a space where he is surrounded by men who are, and will become, some of the largest political figures in American history.

The political is becoming proximal and personal.

Uncle JJ didn’t just introduce Monroe to politics. He helped usher him into the revolutionary world taking shape around him—and Monroe, as he would do over and over again throughout his life, followed the people he trusted into the action.

And then, at 17, while Monroe was studying at William & Mary, Virginia’s royal governor, the Earl of Dunmore, dissolved that same House of Burgesses.

Monroe was so mad that he left his studies and enlisted in the Virginia Infantry.

Which is something we’re going to see happen again.

And again.

And again.

Monroe had a habit of putting his personal life, his education, his career—even his financial security—on pause when he believed something bigger required his attention.

He could be studying.

He could be farming.

He could be practicing law.

But if he felt called to serve, if he thought the country needed him, or if someone he admired needed him, he would come running back to politics.

And then somebody would piss him off. Or his finances would get too shaky. Or he’d get tired of the whole damn thing.

And he’d take himself home.

Back to his farm. Back to his normal life.

Until, inevitably, something—or someone—pulled him back in.

That pattern started young.

So did another one.

Monroe was described as being somewhat of a serious person. Almost somber. He wasn’t particularly gifted at conversation, but he was cordial, friendly, warm, and sincere in his letters, which he began routinely writing around this same time. Those letters would eventually become one of the ways Monroe built and maintained friendships and political relationships across Virginia and, eventually, the country.

The Revolutionary

Monroe left William & Mary, joined the Virginia militia, and got straight to work. Eventually, that service turned into an appointment in the Continental Army, where Monroe joined Washington’s forces in New York.

Which, naturally, Uncle JJ was not particularly thrilled about.

His response was basically: James. Please go back to school.

Because while Monroe apparently saw military service as his grand opportunity to serve his country, Uncle JJ seemed to have a slightly different vision for his nephew’s future.

Go to school.
Study law.
Become a respectable gentleman.
Do something useful with your life.

Honestly, it feels a little like telling a 17-year-old who wants to be an actor or professional athlete to go to college and become a doctor instead.

Except Monroe kept getting opportunities to be a soldier, so he kept trying to take them.

At the Battle of Trenton in December 1776, he led a charge and was shot in the shoulder. He nearly died, but was promoted to captain for his conduct under fire.

And once he recovered from being shot, he went right back.

Apparently getting shot was not enough to convince him that perhaps Uncle JJ had a point.

In 1777, Monroe returned to the Continental Army and became an aide-de-camp to Major General Lord Stirling, also known as William Alexander. Basically, he became a staff officer, working alongside Stirling rather than commanding his own regiment. This put him in the orbit of some of the young men who would become important figures in the new country—including Alexander Hamilton and the Marquis de Lafayette.

And Lafayette wasn’t just some guy Monroe happened to meet.

During the Battle of Brandywine, Lafayette was wounded, and Monroe tended to him. The two developed a lifelong friendship from that experience.

But military glory kept dangling in front of Monroe without him ever quite being able to capture it.

Monroe fought at Brandywine, Germantown, and Monmouth, but by 1778 the Continental Army had more officers than it had troops to command. Monroe had risen to the rank of major, but there simply wasn’t much opportunity for him to get the glorious field command he wanted.

So in late 1778, he resigned from the Continental Army and went back to Uncle JJ.

And Uncle JJ, once again, basically said:

“Now, go study law.”

So Monroe did.

For approximately five minutes.

Then, in 1779, Virginia decided it needed more troops after British raids, and Monroe saw another opportunity to get back into the action. With recommendations from Washington and Hamilton, he received an appointment as a lieutenant colonel and was tasked with raising and commanding one of four new Virginia regiments.

There was just one tiny problem:

Virginia couldn’t actually raise the money needed to raise the troops.

So Monroe had a commission, a rank, and essentially nothing, and no one, to command.

He was big mad. He criticized both the Virginians who weren’t volunteering AND the government that wanted an army without providing the money necessary to build one.

A pretty important preview of the future politician.

But for now, there was no money.

There were no troops.

And no glorious military command.

So…

back to Uncle JJ he went.

Uncle JJ, now Virginia’s chief justice, once again told James to take himself to school.

He sent Monroe back to William & Mary with money for his travel and living expenses and a letter introducing him to Thomas Jefferson, who was then governor of Virginia. Jefferson gave Monroe another military-related assignment: he was made Virginia’s military commissioner to the Southern Army, responsible for helping establish communication between Virginia and the army in the South.

So Monroe was technically studying law.

And technically in military service.

And technically working for the governor.

And technically unable to pick a lane.

But even this didn’t quite work out the way Monroe wanted. Because guess what Jefferson wasn’t able to do?

You guessed it – Jefferson couldn’t actually raise the money needed to raise the troops.

Virginia didn’t have the resources to build the kind of force Monroe wanted to command.

So Monroe went back to just studying law.

And while he was doing that, the war was moving on without him.

On October 19, 1781, the British surrendered at Yorktown. Alexander Hamilton led the assault on a key British stronghold, while Lafayette was among the American commanders on the field.

And Monroe?

He wasn’t there.

After spending years trying to get himself into the action, Monroe had managed to miss one of the most consequential American victories of the entire Revolution.

At this point, maybe Uncle JJ felt like he had finally won.

Monroe had tried the military thing. He had been wounded and promoted. He had managed to work alongside some of the most important young officers of the Revolution and been given opportunities to command. And yet, every time, something had gotten in the way of the military glory he craved.

So Monroe took the advice he’d been getting all along and turned his attention toward government.

Which meant, naturally, that he became a politician.

The Politician

In April 1782, Uncle JJ was reelected to the Continental Congress and recommended Monroe take his seat in the Virginia General Assembly—the state’s legislature. With letters of recommendation from Washington and Jefferson to boot, Monroe easily won the election.

A month later, he was admitted to the bar.

So, once again, Monroe was pulling a both/and: politician and lawyer.

His first term in the General Assembly and Congress wasn’t particularly productive. But Monroe was building something else: relationships. He stayed writing to Virginia politicians and leaders, keeping them informed about what was happening in Congress and asking for their opinions. All that letter-writing helped him cultivate friendships and political connections that would follow him throughout his career.

At first, Monroe was more observer than leader. But as western expansion became a bigger issue, he found his voice. He’d actually traveled through the West and knew what settlers were up against, particularly when it came to getting their goods to market through the Mississippi, which Spain controlled. So Monroe started pushing Congress to do something about it.

And after winning reelection in 1785, he came back with a voice and a plan. He proposed a way for the western territories to join the Union more quickly. He was finally speaking up. Problem was, Congress wasn’t particularly interested in listening.

By 1786, Monroe was exhausted—physically, mentally, and increasingly worried about whether he could afford to keep doing this. Even the savings he’d accumulated disappeared when his broker went bankrupt.

So Monroe resigned from Congress and went back to practicing law.

Politician Turned Lawyer

His reputation as a Revolutionary War veteran and advocate for western interests helped him establish a lucrative law practice.

Unfortunately, “lucrative” wasn’t doing much for his bank account. Many of his clients paid him in what the biography calls “imaginary money”—promises of goods or services rather than actual cash. 🫠

So, naturally, he went back into politics.

Lawyer Turned Politician Again

By April 1787, Monroe had been elected back into the Virginia Assembly, but was still practicing law whenever the legislature wasn’t in session.

Around this time, Monroe wrote to his wife about his determination to prove himself in the Assembly:

“It is necessary not only that I should be faithful and honest but that they should think me so.”

Which tells me the man wasn’t just concerned with doing the right thing. He was concerned with being seen as doing the right thing.

We’re going to come back to that.

Meanwhile, Madison, Washington, and the rest of the delegates were in Philly writing the Constitution. Monroe wasn’t in the room where it happened; he was back in Virginia, practicing law and apparently already missing politics.

When the Constitution came back to Virginia for the state’s vote of approval, Monroe initially sided with Washington and Madison. He thought the Constitution had problems, but the sorry state of the existing national government made him think it was necessary.

Then he went home to Richmond.

And listened to Uncle JJ and his Antifederalist allies RAIL against it.

Suddenly, Monroe was seeing things differently.

He started seeing problems everywhere: too much power for the federal government, too much power for the president, and no bill of rights.

Virginia eventually ratified the Constitution, 89–79. Monroe voted against it. And one of the things he had wanted—a bill of rights—would come a few years later.

By this point, Monroe and Madison had become friends, and both were beginning to orbit within Jefferson’s emerging political circle.

Which made what happened next… awkward.

In 1789, the Antifederalists were determined to keep Madison out of the new federal government. They eventually persuaded Monroe to run against his friend for a seat in the House.

Madison won.

But Monroe and Madison’s friendship survived the whole thing. They continued traveling together and even shared accommodations during the campaign.

For Monroe, he was apparently capable of compartmentalizing the personal and political. He could disagree with Madison politically—and apparently even run against him—without that disagreement wiping out the relationship underneath it.

Quite a feat for a man whose political relationships were so often built through his personal ones.

Politician Turned Lawyer Again

After losing to Madison, Monroe returned to his law practice.

As his political reputation had grown, so had his clientele and public visibility. Monroe began to see a promising financial future in the law.

But then Virginia Senator William Grayson died.

And Virginia elected Monroe to replace him.

Lawyer Turned Politician AGAIN

So, by the fall of 1790, Monroe was back in Congress—this time as a U.S. senator.

And, as he did the first time, he started out relatively quiet.

But that didn’t last long.

After becoming increasingly frustrated with the Senate’s secrecy rules, Monroe made one of his first major pushes for transparency, arguing that the Senate should open its proceedings to the public. He warned that an “abuse of power” could result from being protected from public scrutiny.

The Senate rejected his proposal, 17–9.

And then he started picking fights with George Washington.

In early 1792, Washington nominated Gouverneur Morris as minister to France. Monroe opposed the nomination, arguing that Morris’s business interests created a conflict with his responsibilities as an American diplomat.

The Senate confirmed Morris anyway.

But the episode showed that Monroe was increasingly willing to challenge Washington’s administration. At the same time, he was becoming more closely aligned with Jefferson and Madison and their opposition to Federalist policies.

So Monroe wasn’t exactly cutting ties with Washington. He just wasn’t willing to follow him everywhere, either.

Then Britain and France went to war, and American ships started getting caught in the middle.³Those pesky impressments we’ve talked about before. Washington sent John Jay to Britain and needed someone in France who could explain America’s neutrality and remind the French that, hey, we have treaties. Please respect them.

James Madison wanted no parts of the position.

And neither did two other Republicans.

Which left Monroe.

And in 1794, George Washington sent him to Paris.

The Diplomat

Monroe arrived in Paris ready to prove he could do the job.

And apparently, he made a pretty good first impression. The French welcomed him warmly, and soon Monroe and Elizabeth were being invited to official government receptions.

But Monroe wasn’t taking any chances.

Remember that letter to his wife where he said it wasn’t enough to be faithful and honest—people needed to think he was faithful and honest?

Yeah. That was still very much a thing.

Worried that Federalists in Washington might blame him for any deterioration in Franco-American relations, Monroe began sending James Madison confidential copies of his reports from Paris—in effect, duplicates of everything he was sending to Secretary of State Edmund Randolph.

He wanted a record.

He wanted Madison to know what he was doing.

Most importantly, he didn’t want anyone back home thinking James Monroe wasn’t doing his job.

Then, Monroe gave a speech to the French Convention,⁴The Convention was the governing body of revolutionary France at the time. and the British weren’t thrilled about it. Word soon arrived that British officials had objected to it and threatened to disrupt John Jay’s negotiations in London because they feared Monroe was negotiating some kind of military alliance with France.

The State Department wasn’t thrilled either.

Randolph sent Monroe a sharp reprimand, telling him,

“We do not perceive that your instructions have imposed upon you the extreme glow of some parts of your address.”

Monroe was astonished.

So he went back and reread his original instructions.

Then he reread Randolph’s letter.

And decided, Nope, I’m not crazy.

Monroe wrote back expressing his “surprise and concern” over the criticism and insisting that his speech had not contained a single word or phrase that differed from the instructions he’d been given.

Meanwhile, I’m still trying to figure out how this biography keeps talking about how poor Monroe was while also describing all the opulent things he and Elizabeth were buying and enjoying in France. 🧐

At one point, the Monroes moved into La Folie, which the biography describes as the richest and most beautiful home Monroe had ever lived in. They entertained lavishly and were living a life that was, let’s just say, a little different from the financially precarious existence we’ve heard so much about.

I’m not saying this is important to the plot.

I’m just saying…

…

ANYWAY.

By the end of 1795, things with France were getting complicated.

The Monroes had sheltered people who the French government considered enemies, and then came Jay’s Treaty.

Jay had negotiated from a pretty weak position.⁵Imagine humongous air quotes around “negotiated.” Britain remained the world’s dominant naval power and had little incentive to give the Americans everything they wanted. Or really, much of anything they wanted.

So Jay got what he could get.

Which left Monroe in Paris trying to explain an agreement he hadn’t negotiated and couldn’t control.

He did his best to calm French officials. He then wrote to the State Department insisting that “it was in the interest of America to avoid a rupture with France” and that he had “done all in my power to prevent it.”

But Monroe had no idea what was happening at home.

Which is that things were getting messy.

Randolph was accused of seeking a bribe to disclose the terms of Jay’s Treaty to the French government. Washington, who had known Randolph for years, concluded that his secretary had betrayed his trust. Randolph resigned.

Washington replaced him with Timothy Pickering, a strong Federalist and supporter of closer relations with Britain.

And Pickering was not exactly inclined to give Monroe the benefit of the doubt.

So Monroe was over in France trying to keep the relationship with France from completely falling apart while the people back in Washington were making political moves that would eventually determine what happened to him.

With Pickering’s encouragement, Washington came to believe that the French government’s “suspicions, doubts, and discontentment” were evidence of Monroe’s failure as American minister.

So Washington recalled him.

The State Department formally presented Monroe’s recall on December 9, 1796.

And Monroe was hurt.

He had spent three years trying to do the job he’d been given, and he believed he’d followed his instructions. Now he felt betrayed by two secretaries of state and abandoned by the president he’d admired since he was a boy.

Washington was one of the first major political figures Monroe had ever encountered—a man Uncle JJ had introduced him to when he was a teenager.

And now that man had decided Monroe had failed him.

Monroe’s response?

He gathered his notes and correspondence from his time in France and wrote A View of the Conduct of the Executive, in the Foreign Affairs of the United States, connected with the Mission to the French Republic, during the Years 1794, 5, and 6.

He cited his official correspondence with the State Department and laid out his case showing he had followed his instructions and why he believed the Jay Treaty had created precisely the kind of problems with France that those instructions hadn’t prepared him to handle.

The book was praised by Francophiles and Republicans and attacked by Federalists and Anglophiles.

And by the time Monroe’s book made its way into the political world, George Washington was no longer president.

John Adams had taken office in March 1797.

And Adams was not impressed. He described the View as:

“a studied insult to the government of my country…by a disgraced minister, recalled in displeasure for misconduct.”

At this point, Monroe was done.

He decided to abandon public service and return to Virginia to rebuild his law practice.

But he still had to get home.

Monroe had left America for France in June 1794.

He returned on June 27, 1797.

Three years and nine days later.

When he left, George Washington was president.

When he came back, John Adams was president.

The political world he had left behind had kept moving without him.

Once again, Monroe wasn’t in the room where things were happening.

He came home to a government that had changed, a president who no longer trusted him, and a reputation he had just spent months trying to defend.

So for the moment, he was done with politics.

James Monroe went home.

Governor

And for a little while, he actually stayed home.

He settled back into Virginia and his law practice, presumably ready to enjoy the private life he kept threatening to choose.

But you see the name of this section, right?

Virginia had other plans for him and in December 1799, the State Assembly elected him governor.

However, Virginia’s constitution had intentionally kept the role of governor pretty limited, so Monroe was essentially a figurehead for the state—with a modest income and not a whole lot of actual power.

Except James Monroe didn’t know how to just sit down somewhere.

He took a position that was supposed to be fairly limited and started making it mean something.

He used his ability to speak before the Council to push for government reforms, more responsible fiscal policies, and appointments based on merit rather than party connections or family influence. He also pushed the state to take on responsibilities that had largely been left to local governments, including education and road maintenance.

By the time he finished his first stint as governor, Monroe had helped turn the office into a much more consequential platform for shaping state policy.

What a very Monroe thing to do.

You can see the pattern I talked about at the beginning, right? Monroe kept getting pulled back into public life, even after deciding he was ready to go home and be a private citizen.

Except this time, something felt a little different.

His years in France had put him on an international stage and forced him to see himself as something more than the younger man standing beside Uncle JJ, Washington, Jefferson, Madison, and everyone else he had spent years looking up to.

Maybe Monroe was finally starting to believe that he was just as capable of doing what needed to be done as any of them.

And he was going to need to keep that same energy.

Because Thomas Jefferson was about to need somebody in France.

Diplomat Once Again

The Louisiana Purchase: Monroe Edition™

Needless to say, Monroe’s first trip to France had ended…poorly.

Now it’s 1803, Jefferson’s president, and the situation in France has changed dramatically.

Jefferson was increasingly concerned about western settlers’ access to the Mississippi River. New Orleans was the key to that access, and Jefferson did not want France—or anybody else—to control the city and potentially cut the United States off from one of the most important trade routes in the West.

So Jefferson sent Robert Livingston, the American minister to France, to negotiate for New Orleans and West Florida. And he sent Monroe to join him.

The instructions were pretty straightforward: try to get New Orleans and the Floridas for up to $10 million.

Napoleon had originally planned to rebuild French power in North America, but those plans were falling apart. His forces were struggling in Saint-Domingue (now Haiti), Britain was ONCE AGAIN at war with France, and suddenly maintaining a massive French territory in North America didn’t look nearly as attractive as it had before.

So Napoleon made them an offer.

The entire Louisiana territory.

For $15 million.

Monroe and Livingston had absolutely no authority to buy the entire thing.

They bought it anyway.

And this is one of the funniest little ironies in Monroe’s career: this was the same James Monroe who had spent his first diplomatic mission worrying himself sick about following instructions and proving that he was, in fact, doing what the administration told him to do.

Now he was being celebrated for doing the exact opposite.

For four cents an acre, the United States more than doubled in size.

And Monroe was suddenly not just the younger guy hanging around the edges of major events.

He had helped make one happen.

Diplomat to England

Monroe wasn’t done.

Rufus King resigned as America’s minister to Britain, and Madison sent Monroe to London in 1803 to take his place. His assignment this time?

Get the British to stop impressing⁶You should know what this means by now, Friend. American sailors and leave American ships alone when they were trading with other countries.

The Monroes did not exactly thrive in London.

The weather was miserable. British officials weren’t interested in giving Monroe what he wanted. Social invitations dried up.

And Monroe was starting to wonder, once again, whether he could actually afford to keep living the diplomatic life.

By 1804, he was seriously considering going home and practicing law.

Again.

Been Around the World and I-I-I

But, before Monroe could fully retreat into private life, Madison, now Secretary of State, sent him to Spain to negotiate over Florida, part of the original instructions when he visited France. But, once Monroe got to France, he found out that Florida had never been ceded to France, it was still under Spanish rule.

Well, the Spanish weren’t interested in selling, and France wasn’t interested in helping. Monroe also had to deal with Robert Livingston, who had apparently decided to make his own deal and was offering an absurd amount of money for Florida.

Monroe shut that down.

He wasn’t going to agree to pay for territory he believed the United States had already purchased as part of Louisiana.

The bigger takeaway, though, was what Monroe learned from the whole mess.

He had gone into diplomacy believing that governments born out of revolutions, like France and the United States, might naturally share some of the same ideals—things like individual liberty and representative government.

He came out of it understanding something much more cynical:

A country’s first priority is its own interests. And when those interests conflict with everything else—ideals, friendships, treaties, whatever—those other things can suddenly become pretty flexible.

That lesson would stick with Monroe.

It would shape the way he thought about American expansion and foreign policy for the rest of his career.

The Breakup

By this point, Monroe had been in Europe for years, yet Britain still wasn’t giving him what he wanted.

Jefferson eventually sent William Pinkney to join him in negotiating with the British.

The problem?

Monroe found out about it from the newspapers.

Not Jefferson.

Not Madison.

The newspapers.

And considering Monroe’s whole “I need people to think I’m doing my job” thing, you can probably imagine how well that went over.

Monroe felt like his two closest political and personal friends had basically sidelined him.

He had wanted to finish his European career with another major diplomatic achievement—something to go along with the Louisiana Purchase.

Instead, he was getting replaced.

And there were already people in Monroe’s ear suggesting that maybe this wasn’t just about foreign policy. Jefferson had made it pretty clear that he wanted Madison to succeed him, and Monroe had just spent years building his own reputation overseas. Cynics could certainly speculate that keeping Monroe from adding another diplomatic win to his résumé was one way to make sure Madison stayed the obvious choice.

Monroe wrote to both of them, making it pretty clear that he would have appreciated, at minimum, a heads-up.

Jefferson tried to smooth things over.

Madison wasn’t nearly as interested in smoothing anything over.

And Monroe was starting to think about what came next.

Maybe if Jefferson and Madison didn’t think he was the person for the job, he could find a different way to prove them wrong.

For the moment, though, he still had one more thing to finish in London.

And that was where things got even messier.

The Treaty That Made Everything Worse

The Monroe-Pinkney negotiations eventually produced a treaty with Britain, but it didn’t resolve the issue Monroe had been sent to address: impressment. Jefferson refused to submit the treaty to the Senate.

From Jefferson and Madison’s perspective, the treaty wasn’t good enough.

From Monroe’s perspective, they were rejecting the best deal Britain was willing to give them—and making him look like the failure.

And now the personal stuff was tangled up in the political stuff.

Almost as a consolation prize, Jefferson offered Monroe governorship over the Louisiana area Monroe had just secured. A position he had offered Monroe before and that Monroe had declined.

Which tells you something about how complicated this had become.

Monroe was being offered a major position while simultaneously feeling like Jefferson and Madison were pushing him out of the political future he’d spent decades working toward.

He went home to Virginia in 1808.

And by the time he got there, Monroe had decided he was done playing games.

He considered challenging Madison for the presidency.

Now, he didn’t campaign aggressively, and Madison ultimately won the Democratic-Republican nomination, but the damage to the friendships had been done.

Monroe and Madison wouldn’t speak or correspond for more than two years.

Jefferson, however, was a different story.

Monroe still wanted to preserve that relationship. He wrote Jefferson explaining his decision and made clear that, whatever happened politically, he didn’t want to destroy their friendship.

Jefferson eventually wrote back with his own apology and plea for reconciliation.

Monroe accepted it.

He could forgive Jefferson.

Madison would take longer.

And that was really the thing about Monroe.

He could disagree with people. He could challenge them. He could even run against them.

But he didn’t stop caring about the relationship underneath the politics.

So Monroe went home.

Not because he had stopped caring about politics. And definitely not because he had stopped caring about what Jefferson and Madison thought of him.

He just wasn’t quite sure where he fit anymore.

For the first time in a long time, there wasn’t an Uncle JJ, Washington, Jefferson, or some diplomatic assignment pulling him toward the next thing.

There was just Monroe, back in Virginia, figuring out what came next.

Reconciliation

Except Jefferson wasn’t quite ready to let Monroe disappear back into private life.

Madison, too, had a problem.

His presidency was already struggling, particularly when it came to dealing with Britain and France, and he needed somebody with actual diplomatic experience.

So he started putting out feelers to see if Monroe might be willing to come back.

Monroe’s response was basically: I’m always willing to serve my country.

But inside, I can imagine he was more like:

Then, Madison tried offering him the Louisiana governorship again.

For the third time.

Monroe was not interested.

He eventually agreed to return to public life, but he wasn’t willing to just pretend none of the previous stuff had happened.

When Madison offered him the position of Secretary of State in 1811, Monroe made it clear that he had some conditions.

He wanted Madison to acknowledge that bringing him into the administration was more important than keeping him in Virginia. He wanted the freedom to actually do the job rather than serve as Madison’s puppet. And, perhaps most importantly, he wanted some acknowledgment that the whole mess with Britain had not simply been his fault.

Madison finally gave him what he needed.

He told Monroe that the disagreement over the British treaty had been a matter of different interpretations—not that Monroe had failed to follow instructions.

That was enough.

Monroe accepted the position.

After more than two years of not speaking to Madison, the two men were working together again.

Not exactly besties yet.

But they were getting there.

So, after years of getting pulled in and out of public life, Monroe had landed somewhere pretty important.

Secretary of State.

And the country was a mess.

Secretary of State

Britain was still messing with American ships and sailors. France was doing its own version of the same thing. Madison wanted Monroe to try diplomacy before things got worse.

Monroe went to work.

His negotiations with France actually got somewhere. The French agreed to release many of the American ships they had seized and resume limited trade.

Britain was a different story.

By 1812, the situation had gotten bad enough that Monroe was openly calling for war with Britain. Four days after he made that statement, Madison asked Congress to declare it.

The War of 1812

But see, what had happened was…

Remember how we talked about how time moved differently back then and how Monroe had spent years and years away from America? Well, that time difference impacted correspondence as well.

And so…

Y’all, Britain had already signed the Treaty of Ghent before war had even been declared. Americans had just heard the news late. So, the war ended without actually resolving the original impressment issue through the treaty itself.

And the end of the Napoleonic Wars had changed the situation more than anything else: Britain no longer needed to seize sailors and interfere with American shipping in quite the same way.

But Americans got some dramatic military victories right around the same time the peace arrived, so the whole thing was eventually remembered as a second War of Independence.

History, and America, loves a good victory lap.

And when British forces threatened Washington, D.C. in 1814, Monroe went to Madison with a warning that the British were coming. He was right.

The British burned Washington.

Afterward, Monroe temporarily took over the War Department while Madison looked for a permanent secretary. Yes. This man was acting as two entire Secretaries. He used the opportunity to push for changes to the military, including a much larger standing army.

At this point, Monroe was no longer just reacting to what other people were doing. He was making big D Decisions in a country dealing with war, foreign powers, and the very real question of how much the federal government needed to do to actually defend the country.

And some of those decisions meant changing positions he’d held for years.

Monroe had spent much of his political life wary of things like standing armies and concentrated federal power. Now he was advocating for a much larger military because he had seen firsthand what happened when the country wasn’t prepared.

Call it changing your mind.

Call it being committed to your ideals until you’re the one responsible for carrying them out.

Either way, Monroe was making decisions now.

And he had been right about a lot of things.

Can you imagine the ego boost?

By the time the war was over, Monroe had become one of the most prominent figures in the country.

Which meant there was really only one question left.

President

Well, what was next was the presidency.

On March 4, 1817, James Monroe was inaugurated as the fifth president of the United States.

Madison had followed Washington’s precedent of serving only two terms, and after everything Monroe had done over the previous few years, extending the Virginia Dynasty to a third president probably seemed like the obvious choice.

And Monroe was a man with a plan.

He wanted to unify the country, strengthen its defenses, and grow the economy.

Now, when I say unify the country, I mean it. He even believed political parties weren’t necessary.

And thus, the Era of Good Feelings.

He began by traveling around the country, meeting with people from different regions, visiting cities and towns, and generally making himself very available to the public.

People loved it.

Monroe came home convinced he had accomplished what he set out to do: he had brought the country together.

Okay, to be fair, there really was less open partisan conflict than there had been under Washington, Adams, and Jefferson. The Federalists were fading, the economy was doing well, and Monroe had a reputation for being approachable and reasonable enough.

But there was a difference between not having a major opposing party and actually having a politically unified country.

A lesson Monroe was about to learn the hard way.

Florida

The first real test of Monroe’s new vision of national unity came from Florida.

At the time, Florida was still Spanish territory, and the U.S. had been dealing with attacks along the southern border from Seminoles and from Black people who had escaped slavery and found refuge among Seminole communities in Florida.

So, Florida wasn’t just a place where Seminoles lived beyond American control. It had also become a place where people fleeing enslavement could find some measure of safety from slave catchers trying to drag them back into slavery. American slaveholders saw those communities as a threat, and the U.S. government increasingly viewed them as a problem to be eliminated.

Monroe decided something needed to be done.

So he sent Andrew Jackson.

Okay, I know I haven’t been the most objective in these posts. But y’all. My hatred for Jackson burns with the flame of a thousand suns.

Anyway.

Jackson had been sent into Florida to deal with Seminole resistance and attacks along the border. Monroe’s instructions were vague enough that Jackson interpreted them… generously.

And this was not exactly a peaceful expedition.⁷But honestly, how many actually are?

Jackson’s forces burned Seminole towns and destroyed villages. They captured and executed Indigenous leaders, including Josiah Francis and Homathlemico. Jackson also seized the Spanish forts at St. Marks and Pensacola and, after taking Pensacola, had two British subjects, Robert Ambrister and Alexander Arbuthnot, executed.

So, naturally, Congress started asking questions.

Because Jackson had just invaded Spanish territory even though the U.S. wasn’t at war with Spain. So Congress had a pretty reasonable question: Who exactly gave him permission to do that?

Now, at this point, Monroe could’ve thrown Jackson under the bus.

But he didn’t.

To be fair, Monroe’s administration did consider backing away from what Jackson had done, and Monroe eventually ordered the Spanish forts returned. But he also saw what Jackson had done as an opportunity. Jackson had put the U.S. in a much stronger position with Spain, and Monroe’s administration used that leverage to basically tell Spain: either get control of Florida or give it to us.

And that’s exactly what happened.

The Adams-Onís Treaty officially made Florida part of the United States. Spain gave up the territory, and the U.S. agreed to pay $5 million in claims against Spain.

And you would think that would be the end of the Jackson-and-Florida drama.

It was not.

After Florida officially became U.S. territory, Monroe appointed Jackson as its first territorial governor. And Jackson managed to create another diplomatic headache almost immediately.

The outgoing Spanish governor, José Callava, was supposed to turn over official records as part of the transfer of power. When there was a dispute over some of those documents, Jackson had Callava arrested and ordered Spanish officials out of the territory.

This caused another uproar.

And once again, Monroe defended Jackson.

At this point, I have to start wondering what exactly Jackson would have had to do for Monroe to say, “Okay, Andrew. This time you’ve gone too far.”

Because this wasn’t just Monroe defending a military commander whose actions had gotten controversial. This was becoming a pattern.

Jackson eventually resigned as governor and accused Monroe of having put him in an impossible position because of political enemies who wanted him to fail. And apparently, that letter hit Monroe hard.

Which is…interesting.

Because by this point, Monroe had spent years defending Jackson’s actions, protecting his reputation, and treating him as someone he could trust.

And Jackson still wasn’t satisfied. 🙄

Which, honestly, brings us back to Monroe.

Monroe had ideals. Principles. Strong opinions about constitutional limits and the proper role of government.

Until he was the one in charge.

Then things could get… flexible.⁸Sound like anyone we already talked about???

And for a while, that flexibility seemed to work out pretty well.

The Era Starts Cracking

The Monroe presidency really did look pretty good for a hot minute.

The country was expanding. Roads and canals were being built. The national debt was falling. New states were joining the Union.

And Monroe was starting to believe that maybe this whole national-unity thing was actually working.

Then came the Panic of 1819.

The economy crashed. Banks failed. People lost jobs, homes, and land they’d bought with borrowed money.

The “Era of Good Feelings” suddenly had considerably fewer good feelings.

Monroe’s response was limited, partly because the federal government didn’t have the tools—or, in many cases, the political support—to do much about the crisis. He believed economic downturns were a natural part of a developing economy and expected things to recover.

They eventually did.

That didn’t make the people who lost everything feel particularly better in the moment.

And then came Missouri.

Which brings us to slavery.

But, we’ll save that mess for the On Slavery section.

The Monroe Doctrine

There is, of course, one more thing we need to talk about.

The Monroe Doctrine.

This is the part of Monroe’s presidency that tends to get turned into a giant presidential achievement: Monroe standing up to Europe and basically declaring, This hemisphere is ours now.

And, well…

As with everything else, there’s more to it than that.

By 1823, several countries in Latin America had declared independence from Spain, and there were concerns that European powers might try to help Spain take those colonies back. Monroe and his Secretary of State, John Quincy Adams, saw that as a threat to U.S. interests.

The basic idea was pretty straightforward: Europe could handle its European problems, and the United States would stay out of them. But European powers were supposed to stay out of the Americas, too.

No new European colonies.

No European powers coming in and trying to control the newly independent countries in the Western Hemisphere.

Basically: y’all do your thing over there. We’ll do our thing over here.

Monroe had spent years as a diplomat watching countries make decisions based on their own interests. France had certainly taught him that much. The idea that the United States should protect its own interests and avoid getting dragged into European wars made sense.

But there’s another piece to this.

The United States wasn’t simply saying, “Please leave these new countries alone because they deserve to be independent.”

It was also saying, “Please leave these countries alone because Europe controlling this hemisphere is bad for US interests.”

And that distinction matters.

The Monroe Doctrine drew a line between Europe and the Americas, but the United States was increasingly thinking of the Western Hemisphere as its own sphere of influence. The country was expanding westward, looking toward its “natural” boundaries, and becoming more interested in controlling territory and limiting European influence close to home. The State Department itself describes the doctrine as establishing separate spheres of influence between Europe and the Americas.

So when we strip away the shiny “Monroe stood up to Europe!” version of the story, it gets a little more complicated.

The whole thing starts feeling less like “everybody gets to be free!” and a little more like “we’re claiming the Western Hemisphere as our sphere of influence, thank you very much.”

That doesn’t mean the Doctrine had no meaning for the newly independent countries of Latin America. It did. It warned European powers against trying to reestablish colonial control, and the United States presented itself as opposing that kind of intervention.

But it also tells us something important about Monroe.

He wasn’t suddenly abandoning the idea that countries act in their own interests.

He was finally in a position to make American interests the thing everyone else had to consider.

And there was one more little complication.

The Monroe Doctrine is named after Monroe, but John Quincy Adams was heavily involved in developing the ideas behind it. Adams was particularly opposed to making the declaration jointly with Britain because he didn’t want the United States simply attaching itself to British foreign policy. He wanted the United States to establish its own position.

So yes, Monroe delivered the Doctrine.

But put some respect on my boy, JQA’s name!

It was Monroe, Adams, and a United States that was becoming increasingly confident about its place in the Western Hemisphere.

And increasingly confident about what it believed that place should be.

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By the end of Monroe’s presidency, the “Era of Good Feelings” looked considerably less good.

The political divisions Monroe thought he had eliminated were coming back. His own cabinet members were positioning themselves to succeed him. Congress was becoming more divided. And Monroe, who had spent years believing that personal relationships could hold political disagreements together, found himself increasingly unable to control the ambitions of the people around him.

The irony is that Monroe had spent his entire career trying to get back into the room.

Now he was sitting at the head of the table.

And he was finding out that being the person in charge did not mean you got to control what everybody else did.

On Slavery

Okay. This is going to be a little different from the slavery sections we’ve had so far.

With Washington, Adams, Jefferson, and Madison, I spent a lot of time talking about their personal relationships with slavery—who they owned, how they treated enslaved people, what they wrote about slavery, and the various ways they justified living within the system.

With Monroe, I want to spend more time looking at what he actually did politically about slavery.

Because Monroe understood that slavery was becoming a bigger and bigger problem.⁹And to be clear, I’m talking about the institution becoming a bigger and bigger problem.

And he had been thinking about that problem for a long time.

First, Let’s Talk About Cotton

For much of Monroe’s early life, tobacco was top dog when it came to the South’s most profitable crops. Tobacco required a lot of skill and labor, and plantations relied on enslaved workers with specialized knowledge of planting, harvesting, and processing the crop. That also meant planters had an economic incentive to provide some level of care for enslaved families, including children and older people who weren’t able to work. On some plantations, as many as two-thirds of the enslaved population might not have been directly working with the crop.

But, Big Cotton changed all that.

The invention of the cotton gin made processing cotton much faster, and as demand for cotton grew, cotton production exploded across the South. Cotton fields didn’t require the same specialized skills to plant and harvest. Women, children, and older people could all be put to work as long as they were physically able to stand and walk.

And cotton opened the plantation economy to a much larger group of White farmers. You didn’t have to be a wealthy planter with hundreds of enslaved people. A small plot of land and enough money to purchase one or two enslaved people could get you into the cotton business.

That also changed the politics of slavery. White laborers and craftsmen who had once opposed slavery because they saw enslaved labor as competition for their own jobs could now become slaveholders themselves.

Slavery was no longer just something wealthy plantation owners were invested in preserving. More White Southerners had a financial stake in it.

And the system itself was becoming more brutal. The economic value of an enslaved person was increasingly tied to how much labor could be extracted from them, regardless of age or family status.

Cotton didn’t just expand slavery.

It changed what slavery looked like.

And as things became more brutal, resistance to slavery grew.

Slave rebellions were not new, but they became an increasingly terrifying possibility for White Southerners. Gabriel’s Rebellion in Virginia in 1800 was one of several major planned or attempted rebellions that would shape how Southern governments thought about surveillance, policing, and control.

And Monroe was about to get a very personal lesson in just how seriously Virginia took that threat.

Gabriel’s Rebellion

In August 1800, Monroe was governor of Virginia when he learned that an enslaved blacksmith named Gabriel had organized a rebellion involving enslaved people from several surrounding counties.

The plan was to march on Richmond, capture Monroe and other prominent citizens, and demand money and a ship to leave the United States.

A storm prevented the rebels from meeting as planned, however, giving the government time to respond.

Monroe called out the militia, ordered troops to surround Richmond, and sent others into surrounding counties to search for the people involved. Gabriel and dozens of others were eventually captured and sentenced to death.

Gabriel was hanged in October 1800. And this wasn’t meant to be a quiet execution. The hangman deliberately kept him alive and convulsing at the end of the rope rather than allowing him to die quickly, making an example of him for anyone else who might consider rebelling.

Monroe responded by requiring Black people entering Richmond to carry passes and leave the city by sundown.¹⁰HELLO, SUNDOWN TOWN. And Monroe didn’t just see this as an isolated event.

He believed slave rebellions could become more common because enslaved people were increasingly aware of the difference between their own condition and the freedom enjoyed by free Black people. He also worried that existing patrol laws weren’t enough to prevent future uprisings.

Essentially, Monroe was asking:

How do we prevent our chickens from coming home to roost?

The Missouri Problem

By the time Monroe was president, the question was no longer just what individual states were going to do about slavery.

It was becoming a question of what the United States was going to do about slavery as the country expanded westward.

And Missouri was about to make that impossible to ignore.

When Missouri applied for statehood in 1819, Congress immediately got into a fight over whether it would enter the Union as a free or slave state. The debate became so heated that John Quincy Adams warned that the controversy might be “a preamble” to a much larger national conflict.¹¹You see my boy JQA predicting the future?!

Monroe not only decided to stay out of the debate, he ordered his cabinet to do the same.

The eventual compromise admitted Maine as a free state and Missouri as a slave state, keeping the balance between free and slave states in the Senate. It also prohibited slavery in the remaining Louisiana Purchase territory north of 36°30′, while allowing slavery south of that line.

So, basically, Congress drew a line across the Louisiana Purchase and said: slavery stops here.

For the moment, anyway.

Monroe signed the compromise. Although he had stayed out of the public debate, he supported the compromise because he believed Congress did not have the constitutional authority to place restrictions on Missouri that hadn’t been imposed on other states. He also feared that the fight could tear the Union apart.

And this is where I have some thoughts.

Because Monroe had spent years getting involved when he thought the government wasn’t doing enough. He fought over roads. He fought over military preparedness. He had very strong opinions about what the federal government could and couldn’t do. His principles could become flexible when he wanted them to.

But when it came to slavery, Monroe’s approach was much more cautious.

He wasn’t pushing Congress to confront the institution.

He wasn’t pushing for abolition.

He was trying to keep the country together while kicking the slavery question a little farther down the road.

So What Did Monroe Actually Think About Slavery?

So far we’ve spent this whole section talking about what Monroe did about slavery politically, but that doesn’t mean he had no personal thoughts about the institution itself.

And as to be expected, his thoughts were complicated.

Monroe clearly understood that slavery was cruel. At one point, he said:

“The God who made us, made the black people, and they ought not to be treated with barbarity.”

But Monroe was also a slaveholder. He continued to own enslaved people throughout his life, including during his retirement. At one point, when he was struggling financially, he sold enslaved people in order to help rescue his brother Joseph from bankruptcy.

So we have a man who could acknowledge the humanity of Black people and recognize the brutality of slavery while still participating in—and benefiting from—the system itself.

Different Founding Father. Same old contradiction. Same frustration on my end.

He knew enslaved people resisted because they wanted to be free and that the institution was becoming increasingly difficult to control.

He just didn’t seem to believe that ending slavery was the answer.

Colonization

Instead, one of the solutions Monroe supported was colonization: removing free and formerly enslaved Black people from the United States and resettling them somewhere else.

After Gabriel’s Rebellion, Monroe supported efforts to remove people considered “dangerous” from Virginia.¹²I added those quotes, because how we defining dangerous??? 👀 Virginia eventually asked Jefferson to help find federal land where people involved in slave rebellions could be relocated, and Monroe suggested finding a foreign country willing to accept them.

That idea eventually became part of a much larger movement.

The American Colonization Society was founded in 1817, and its supporters had different reasons for backing the idea. Some genuinely believed colonization could be part of emancipation. Others wanted to remove free Black people from the United States because they believed they threatened the stability of slavery.

Monroe supported federal involvement in the effort.

In 1819, Congress appropriated money to help the government resettle Africans who had been captured from illegal slave traders. The Monroe administration later helped fund settlements in Africa for emancipated people.

And one of those settlements would eventually be named Monrovia.

So, yes.

There is literally a city in Africa named after James Monroe.

Which is…a choice.

But the important part here isn’t the name.

It’s the solution Monroe was supporting.

The answer to the existence of slavery—and the resistance it produced—was still not end slavery.

It was move the Black people somewhere else.

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From the personal to the political, Monroe’s approach to slavery was pretty consistent.

Although he could recognize that slavery—and the resistance it produced—was a problem that was only becoming larger as the country expanded, his solutions were almost always about managing the consequences of slavery rather than confronting slavery itself.

Monroe spent his career fighting over what the government should do and the powers of the federal government. He was perfectly willing to make himself heard when he believed something mattered, but was all “mum’s the word” when it came to liberating humans.

And maybe that’s because slavery wasn’t an abstract constitutional question for Monroe.

It was part of the country he lived in, the economy he participated in, the society he benefited from, and the people he owned.

So when confronting slavery meant confronting the system that he himself was part of, Monroe’s principles had some limits.

And that’s the thing about compromise.

Sometimes it solves a problem.

And sometimes it just buys you a little more time before everybody has to deal with the problem again.

The Missouri Compromise had bought them time.

America had, once again, found a way to kick the can down the road.

But the road was getting shorter.

The Legacy

So, after all of that, what do we actually do with James Monroe?

Because Monroe is a weird one.

He was the last president of the Revolutionary generation to serve in office. He was the last of the Virginia Dynasty. And he’s generally remembered as the Last Founding Father.

And 🤷🏾‍♀️ that title feels pretty appropriate.

Monroe was born in 1758, grew up in colonial Virginia, fought in the Revolution, knew Washington, Jefferson, Madison, Hamilton, Lafayette, and basically everybody else we’ve spent the last several posts talking about.

But by the time Monroe became president, the country was already changing.

You can see it in something as simple as the way Monroe presented himself at his second inauguration. John Quincy Adams even read Monroe’s outfit for filth, describing his “black suit with knee breeches, long silk hose, and shoe and knee buckles” as “somewhat antiquated.”

The man was still very much a product of the Revolutionary era, but the country around him was moving forward without him. He looked like a man who had walked out of one era and somehow found himself standing in another.

And that was kind of Monroe’s whole life.

He was the Little Brother of the Revolution.

Always trying to catch up.

Always standing near somebody he admired.

Always trying to get into the room.

And then, suddenly, he was the oldest man in the room.

By the time he retired from the presidency in 1825, the country was moving into a new political generation. Monroe went back to Virginia and, at least initially, seemed genuinely ready to leave public life behind. When politicians tried to recruit him for another run for office, he turned them down.

But…

This is James Monroe we’re talking about!

So when Virginia needed delegates for its constitutional convention in 1829, and Madison and John Marshall agreed to participate, Monroe apparently decided that retirement was negotiable after all.

He was elected president of the convention despite his declining health, but was only able to serve for about six weeks before stepping down and returning home.

This time, though, he really was done.

Monroe moved to New York to live with his daughter after Elizabeth died in 1830, and died there the following year.

But if there’s one part of Monroe’s legacy that has stood the test of time, it’s the Monroe Doctrine.

The Doctrine has been used, reinterpreted, expanded, and sometimes outright misused by American presidents in the two centuries since. Its original purpose was to warn European powers against further colonization or intervention in the Western Hemisphere, while establishing that the United States would stay out of European conflicts.

And whatever we think of the Doctrine’s later uses, it became one of the foundational ideas of American foreign policy.

Maybe that’s why The Last Founding Father is such a fitting title.

Monroe wasn’t really the beginning of the American political story.

He was the bridge between what came before and what came next.

He started his career as the young man trying to follow the people who came before him. Washington. Jefferson. Madison. Lafayette. Uncle JJ. Always trying to get into the room.

Eventually, he became the guy at the head of the table. But by the time he got there, the room was changing.

The Revolution was over. The Founders were disappearing. A new generation was coming up behind them.

And Monroe—the Little Man of the House who became the Big Man of the House, soldier, politician, diplomat, farmer, president, and perpetual political boomerang—was the last one left to watch it happen.

He died on July 4, 1831, the same day the country celebrated the Declaration of Independence. John Adams and Thomas Jefferson had died on July 4 just five years earlier.

Three Founding Fathers. Three July Fourth deaths. And with Monroe, the generation that created the country was finally gone.

America had moved on.

James Monroe had finally caught up.

Random, Interesting Facts

Y’all, I wrote the hell out of that ending! But, let’s stop being all sentimental and get to the randomness, because I found out James could be awkward, dramatic, and occasionally one bad conversation away from a duel.

Let’s start with the ladies.

Before Monroe married Elizabeth at 28, he apparently had a little trouble in the romance department. During his first term in Congress, he visited Albany, New York, and one young woman, Sarah Vaughan, wrote about his attempts to woo another young lady.

Her assessment was…not great.

She described poor Col. Monroe as being “in despair” because he had apparently “lost his heart” out in Albany, but feared his feelings were not being returned. While she credited him with plenty of qualities—being rich, young, sensible, well-read, and a member of Congress—she had her doubts about the whole “handsome” and “lively” thing.

In fact, she basically said that unless the dimple in his chin was what counted as beauty, she wasn’t seeing it. 🤣

It seems as though Monroe’s shyness wasn’t helping anything. He tended to talk about serious political and national affairs rather than, you know, flirting like a normal person.

Fortunately for Monroe, Elizabeth did eventually say yes.

But women weren’t the only people Monroe struggled to communicate with.

At one point, he almost got into a duel.

With ALEXANDER HAMILTON.

In 1797, after Monroe returned from France, Hamilton confronted him over the Reynolds affair. Monroe had been one of the men who had investigated Hamilton’s financial dealings with James Reynolds back in 1792, and Hamilton was furious that information from that investigation had eventually made its way into print.

Hamilton showed up at Monroe’s door in New York, very much agitated, and demanded an explanation.

Monroe tried to explain that he had left the papers with a trusted contact in Virginia and hadn’t known they had been published.¹³Any guesses who that trusted contact was? Let’s just say it was a certain somebody whose writings stayed getting leaked.

Hamilton wasn’t having any of it and things started getting heated.

Hamilton accused Monroe of lying.

Monroe, offended, essentially said: Excuse me?!

And then called Hamilton a “scoundrel.”

Hamilton responded that he would meet Monroe “like a gentleman.”

Monroe’s response?

“I am ready; get your pistols.”

Monroe said he ain’t never scared.

The two men were eventually separated by the other people in the room, and the duel never happened. But the argument didn’t end there. They continued exchanging increasingly hostile letters, with the person Monroe chose as his second acting as an intermediary in an effort to keep the whole thing from ending with two former Revolutionary War heroes shooting each other.

And who was Monroe’s Second?

AARON. BURR.

And somehow, Monroe’s connection to Aaron Burr gets even more interesting.

His daughter Eliza later married George Hay, the Virginia attorney who had served as the federal prosecutor in Burr’s 1807 treason trial.

Because apparently once you’re part of the Founding Father Cinematic Universe, nobody is ever more than two degrees of separation away from a scandal.

And I got one more factoid for y’all.

When Monroe returned to Washington in 1819, workers were still restoring the presidential mansion after the British burned it during the War of 1812. By this point, the building was being restored and repainted.

And here’s the funny part: the “White House” wasn’t actually a new name.

The building had been whitewashed as early as 1798, and people had already started calling it the “White House” years before the British ever set it on fire. The name wouldn’t become the building’s official name until 1901.

So, yes. The White House was already the White House when James Monroe moved in.

The Rankings

Okay, I know I’ve been gone for, like, 45 years, so here’s a quick refresher on how these rankings work.

Fave Ranking: Literally, where does this president land on the continuum of love this guy! to absolutely cannot stand this guy!

Presidential Ranking: Did the man do what he said he was going to do? Did he actually execute on the reasons he was elected?

Impact Ranking: Just like it sounds. What’s the man’s legacy? How big of an impact did he have on America, government, politics, or our lives today—whether we realize it or not?

Now.

Fave Ranking: #5

DEAD ASS LAST.

Listen.

I’m still trying to figure out how Monroe probably did the most politically around slavery so far, while simultaneously finding a way to do the least when it comes to actually confronting the institution itself.

He rarely seemed willing to really stand on business.

Except with Hamilton.

Because he ate with that one little bit.

But could the biography have influenced this ranking?

More than likely!

And I have zero shame about that.

Because this biographer was committed to giving James Monroe credit for EVERYTHANG.

The Louisiana Purchase?

Apparently it never happens without Monroe.

The Monroe Doctrine?

John Quincy Adams who?

And poor Monroe was just struggling financially all the time, y’all.

Never mind that this man had the grandest estate in France and spent a fortune shipping everything back home.

Give me a break.

But the worst of it all?

The way this man CAPED for the demon himself:

ANDREW JACKSON.

So yeah.

Dead last.

Presidential Ranking: #3

And I had to go back and reread my justification for Madison because I surprised my own self when I saw where I put him. 😂

But reading it again, I can see it.

And because of that, I have to put Monroe right up under him.

Because as false as some of the mythology around the Era of Good Feelings can be, there really was a period of relative political calm during Monroe’s presidency. The Federalists were fading, Monroe made a real effort to present himself as a president for the whole country, and his administration presided over a period that looked, at least for a while, less openly partisan than what came before.

It didn’t last.

But Monroe should get credit for trying to create it—and for presiding over that period while it lasted.

Because presidentially?

The man got some things done.

Florida became part of the United States through the Adams-Onís Treaty, and the Monroe Doctrine became a major statement of U.S. foreign policy. He also signed the Missouri Compromise, even though the slavery crisis exposed just how fragile that supposed national unity really was.

So yes.

I’m putting him right under Madison.

Impact Ranking: #4

And that may seem low right now, but I have a feeling this is going to hold for quite some time.

Because look at what we’ve got so far.

Washington gave us a country.

Jefferson gave us the Declaration of Independence.

Madison gave us the Constitution.

Monroe gave us the Monroe Doctrine.

And that cannot be denied or disputed. The Doctrine became one of the most influential statements in U.S. foreign policy and remained a major touchstone for American foreign relations in the Western Hemisphere.

But when I’m looking at Monroe’s overall footprint?

Fourth feels right to me.

But go on ahead, MOM, update your own tracker.

And tell me about it in the comments. 😂

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That’s all I got, y’all.

And now it’s time for a nap!

I hope the post was worth the wait. I hope you learned something and had fun while learning it. I hope something in here made you think. Something made you laugh. Something made you want to come back for the next one.

Because the next one?!

Y’ALL DON’T UNDERSTAND.

I’m not even going to keep it mysterious.

The next one is one of my favorite presidents OF 👏🏾 ALL 👏🏾 TIME. 👏🏾

I’m so excited to be SOOOO subjective as I praise and defend my guy.

The man who stood on business so hard, he barely got elected and only got one term. 🤣

The man who got censured because Congress was TIRED of hearing this man talk about abolishing slavery.

The man who said, I’m gonna stunt like my daddy and I dare you to try me the way you tried him.

Next stop?

My guy, John Quincy Adams.