James Madison

Back back back again!

Heeeeeey, Everybody.

So, remember after the Adams and Jefferson posts when I was all:

“I have grown.”

“I have learned.”

“I shall not be fooled by these giant biographies again.”

Remember that?

Well.

What had happened was…

I was once again loud and wrong.

Because when I picked up this Madison biography and saw that it was a respectable 250 pages, I got cocky.

Okay, real cocky.

After surviving 652 pages of Adams and 535 pages of Jefferson, I looked at that little 250-page book and was like:

Reader.

It was not.

Not because the book was especially difficult.

Not because Madison was particularly scandalous.

Not because I found myself spiraling into nineteen pages of notes and existential crises like I did with Jefferson.

No.

The problem was that Madison refused to be messy.

Washington was out here surviving wars.

Adams was arguing with everybody.

Jefferson was generating enough contradictions to power an entire blog series.

Madison?

Madison was thinking.

Thinking about government.

Thinking about liberty.

Thinking about power.

Thinking about how to balance liberty and power.

Thinking about how other people had thought about liberty and power.

Then thinking about whether they were wrong.

The man was aggressively cerebral.

And while I can appreciate that intellectually, it turns out it doesn’t exactly scream “just one more chapter.”

At some point I’d sit down to read and immediately find myself wanting to do literally anything else.

Fold laundry.

Clean my kitchen.

Stare into space.

Start one of the seventeen side quests currently living rent free in my head.¹If you missed the Side Quest discussion, go read my Jefferson post. Just know that I have ideas. Many ideas. Potentially too many ideas.

Research entirely unrelated topics like The Summer House drama between Ciara, Amanda, and West.² A show I’ve never even seen an episode of, by the way.

So while I absolutely could have finished this book much sooner…

I simply did not.

And honestly? I feel like Madison would understand. The man never met a subject he couldn’t spend another three hundred pages thinking about.

But enough about me.

Let’s talk about James Madison.

The so-called Father of the Constitution.

The architect of the Bill of Rights.

America’s first wartime president.

The Original Man Behind the Curtain.

The man who somehow managed to be involved in nearly every major political development of the early republic while remaining substantially less famous than most of the people around him.

And because I’ve finally accepted reality, I’m no longer apologizing for the length of these posts.

At this point I’m convinced they’re all going to be long.

Some presidents are complicated.

Some biographies are complicated.

And apparently I have never once looked at a historical rabbit hole and said:

“You know what? That’s enough information.”

So grab a snack.

Grab a beverage.

Settle in.

Because today we’re talking about the man who spent his life writing notes in the margins of America.

James Madison: The Timeline Edition

Before we dive in, here’s the quick-and-dirty version for those of you who don’t have fifteen pages of notes and a historical obsession.

The Man: A Brief Bio

And perhaps the briefest of the brief.

Because unlike Jefferson, Madison was not out here leaving me nineteen pages worth of contradictions, scandals, leaked letters, and opportunities to raise my blood pressure.

In fact, one of the biggest challenges of writing about Madison is that compared to the three presidents we’ve covered so far, he can seem a little… understated.

But, despite rarely being the loudest person in the room, Madison somehow kept ending up in the middle of everything.

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

James Madison, Jr. was born on March 16, 1751, the eldest son of a wealthy Virginia planter family.

At this point, Virginia is honestly starting to feel like the Founding Father assembly line.

Much like Washington and Jefferson before him, Madison entered life with land, status, connections, and opportunities that many Americans could never dream of.

He also very much lived up to the “Junior” part of his name.

Both he and his father served as colonels in the Virginia militia, but for years Madison was known simply as “the young colonel.”

And he was still being called that until his father died in 1801.

I’m sure there’s plenty of Black folk who can relate to being nearly fifty years old and still being referred to as Junior.

His family was large even for his time.

Madison had eleven siblings, though only six survived into adulthood.

After graduating from Princeton, he returned home and helped educate several of his younger brothers and sisters, who at the time were twelve, ten, eight, and four years old.

And if there’s one thing to know about Madison, it’s that the man genuinely loved ideas.

Books were often his preferred company.

The more he read, the more he wrote.

And the more he wrote, the more he refined his thinking.

Writing wasn’t just something Madison did.

It was how he thought.

Because unlike Washington, whose influence came from action, or Jefferson, whose influence often came from vision, Madison’s power came from analysis.

From preparation.

From understanding how systems worked.

And as we’ll see, that made him uniquely suited for the political world he was about to enter.

Madison also spent much of his life being sick.

Or at least convinced he might be.

The man suffered from recurring bouts of illness, mysterious digestive issues, fevers, rheumatism, and various sicknesses that seemed determined to interrupt major moments of his career.

Which, to hear some biographers tell it, occasionally made him sound like the friend who texts “pray for me” every time they catch a cold.

Despite spending much of his life seeming perpetually one stomach issue away from death, Madison somehow outlived Washington, Jefferson, Adams, and even Monroe.

History is funny sometimes.

At Princeton, Madison developed a reputation for being bookish, serious, and occasionally awkward around strangers.

Which makes it especially funny that his friends remembered him as being kind of a mess.

Because beneath all the constitutional theory and political philosophy was a man who apparently enjoyed jokes involving chamber pots, sex, and other topics I will allow your imagination to fill in.

More importantly, Madison knew how to make and keep friends.

That skill would serve him surprisingly well in politics.

Madison’s personality wasn’t the kind that dominated a room.

His gift was making people comfortable enough to work with him, trust him, and keep working with him.

He knew how to find allies, adjust course when necessary, and keep moving forward.

Those skills would define much of his political career.

Which is why I increasingly found myself thinking of Madison as America’s first true politician.

Not by today’s standards, but more in the original sense.

A coalition builder.

A strategist.

A behind-the-scenes operator.

The guy quietly counting votes while everyone else was busy giving speeches.

And yes.

Before anybody asks.

Madison was about 5’4″.

Which means the Father of the Constitution was also one of the original Short Kings.

Something I can relate to.

And proof that history’s most influential people are not always the ones taking up the most space.

The Revolutionary

Madison did not come to politics with a grandiose veteran story.

No horses shot out from under him.

No crossing icy rivers.

No action-hero origin story.

Instead, he arrived the same way he approached most things:

By studying the problem and somehow making himself indispensable.

In April 1776, Madison was elected to represent Orange County at Virginia’s revolutionary convention. Alongside his uncle, he became part of the group that unanimously instructed Virginia’s delegates in the Continental Congress to support independence from Britain.

Not bad for a twenty-five-year-old.

Soon afterward, Madison was appointed to help draft Virginia’s Declaration of Rights.

And this is where we get some of our earliest evidence that Madison, much like Jefferson, could occasionally drop bars.

Most of the document was written by George Mason, a respected statesman nearly twice Madison’s age. But some of Madison’s revisions proved incredibly important.

One in particular stood out.

Mason had written that people should enjoy “the fullest toleration” in matters of religion.

Madison said nah.

Because to Madison, toleration implied hierarchy. For there to be tolerance, someone had to be in a position to tolerate.

Someone powerful deciding who deserved freedom and who didn’t.

Instead, Madison argued that:

“All men are equally entitled to the full and free exercise” of religion.

And if that sounds familiar, that’s because religious liberty would become one of the defining themes of Madison’s political life.

The following year brought a lesson that many ambitious young politicians learn sooner or later:

Voters sometimes just be doing too much.

In 1777, Madison lost reelection, which would be a rare occurence for him.

Why did he lose, you ask?

At the time, candidates were expected to provide food, entertainment, and most importantly, alcohol to potential voters.

Think: less campaign rally, more open-bar tailgate.

As Madison later explained, candidates who refused to play by these unwritten rules were viewed as cheap, arrogant, and/or disrespectful.

His opponent had no problem playing the game.

Madison wanted no parts of it.

So Madison lost.

And judging by the fact that he was still complaining about it forty years later, he never quite got over it.

Fortunately for him, his political career was not about to end.

Later that same year, he was appointed to Virginia’s Governor’s Council, helping advise the governor on executive decisions.

A few years later, Virginia sent him to Congress.

And this is where Madison began developing into the political figure we recognize today.³If you recognize him at all. Don’t worry, I indeed know who my audience is.

During the final years of the Revolutionary War, Congress was dealing with military problems, financial problems, administrative problems, and the general chaos that comes with inventing a government while simultaneously fighting a war.

Madison wasn’t the most charismatic member.

He wasn’t the loudest.

He wasn’t even particularly social.

Which is probably why Congress immediately gave him Hamilton.

One congressman’s wife described him as

“the most unsociable creature in existence.”

But Madison was reliable.

He attended meetings, learned the details, and did the work.

And perhaps most importantly, he learned that losing a vote wasn’t necessarily the same thing as losing the argument.

Because if you couldn’t win the decision itself, you could still influence how the decision got implemented.

And if that sounds like politician behavior…

Congratulations.

We’re starting to meet the real James Madison.

The revolutionary years also introduced him to many of the people who would shape the rest of his life.

Including a young congressman from New York named Alexander Hamilton.

The two men could not have been more different.

Madison was the wealthy Virginia planter’s son who spent his spare time reading.

Hamilton was an immigrant orphan who seemed to arrive in every room at full volume.

Madison spent two years mostly silent in Congress.

Hamilton gave a major speech almost immediately after arriving.

And yet they recognized something in one another.

Both were ambitious, brilliant, and deeply invested in the future of the United States.

Sometimes they were allies.

Sometimes they were rivals.

But from this point forward, neither would be able to avoid the other.

And perhaps the most important thing Madison gained from the Revolution wasn’t a military victory or a political office.

It was a realization.

The United States had won independence.

But the government holding it together wasn’t working.

And Madison was already beginning to think about what came next.

On the Constitution

If Jefferson was obsessed with the question:

“How do we preserve liberty?”

Madison became obsessed with:

“How do we keep this whole thing from falling apart?”

Because after independence, America had a problem.

Actually, several.

The Revolutionary War had been won.

The British were gone.

Mission accomplished.

Except now thirteen former colonies were trying to function as one country, and it was becoming increasingly obvious that the existing government wasn’t up to the task.

States argued with one another.

Ignored national priorities.

Ignored Congress.

Sometimes ignored one another entirely.

And Madison hated it. Not because he wanted a king or some all-powerful central government.

But because he believed a government needed enough authority to actually govern.

Otherwise, what was the point?

At the time, the United States was operating under the Articles of Confederation.

Think of it as America’s first draft.

And like many first drafts?

It had issues.

Congress could ask states for money.

States could say no.

Congress could make decisions.

States could ignore them.

The national government existed, but it often lacked the power to actually do much.

Watching all of this go down had Madison convinced that independence alone wasn’t enough.

The country needed a stronger framework.

A stronger system.

A stronger Constitution.⁴ You see what I did there?😏

So Madison did what Madison always did.

He disappeared into research.

By the time delegates gathered in Philadelphia in 1787 to discuss fixing the Articles of Confederation, Madison arrived with homework completed and extra credit finished.

This man showed up with a PLAN.

Literally.

The Virginia Plan.

His proposal called for a stronger national government with separate branches of power and enough authority to keep the states moving in roughly the same direction.

At the center of Madison’s thinking was a belief that government should ultimately derive its power from the people rather than from kings, nobles, or hereditary privilege.

Which sounds obvious now. But, at the time?

Not so much.

Madison believed the larger and more diverse the country became, the harder it would be for any single group to dominate everyone else.

Different interests would compete. Regions would compete. Factions would compete.

And somehow, through all that competition, freedom would be safer.

Not because people would suddenly become virtuous.

But because nobody would be able to gain enough power to control everyone else.

Whether that actually works in practice remains an ongoing national group project.

But it was a remarkably influential idea.

And while many people contributed to the Constitution, Madison somehow managed to be involved in nearly every part of the process.

He helped draft it, debate it, negotiate it, refine it, and eventually helped defend it.

Because writing the Constitution turned out to be only half the battle.

Now Americans had to be convinced to adopt it.

And that fight was brutal.

Many people worried the proposed Constitution gave too much power to the national government.

Others worried it didn’t protect individual rights strongly enough.

In other words:

The arguing had only just begun.

To help persuade the public, Madison joined Alexander Hamilton and John Jay in writing a series of essays defending the proposed Constitution.

These essays became known as The Federalist Papers.

Think of them as the Founding Fathers’ version of a very long, very nerdy op-ed series explaining why everyone should support the new government.

You know…absolutely nothing like a very long, very nerdy opinion series explaining each President in chronological order.

And if America needed essays, by God, Madison was ready.

Mind you, Madison was writing many of these essays while suffering through one of his recurring stomach ailments.

Which feels relevant because in Federalist No. 19 he described the Holy Roman Empire as being:

“agitated with unceasing fermentations in its own bowels.”

And listen.

I’m not saying Madison was projecting.

But I’m not not saying it either.

Now, one of the biggest objections people had was the lack of a Bill of Rights.

Ironically, Madison initially wasn’t convinced one was necessary.

In fact, he worried that creating a list of protected rights might accidentally imply that any rights not listed no longer existed.

Which…

🤷🏾‍♀️

Fair point.

But politics requires flexibility.

And unlike some people we’ve discussed, Madison could occasionally change his mind without pretending he’d been saying the new thing all along.

Eventually, he became the principal architect of the Bill of Rights itself.

Which feels very Madison.

First he argued against it.

Then he wrote it.

By the time Americans approved the Constitution and the new government officially became reality, Madison had become one of the most influential political figures in the country.

The Constitution.

The Federalist Papers.

The Bill of Rights.

The House of Representatives.

Everywhere you look, Madison’s fingerprints are there.

Which is why many people eventually started calling him the Father of the Constitution.

Not because he created it alone.

But because at nearly every major stage of its creation, defense, and implementation…

James Madison was there.

Usually with a plan.

And almost always with a suggestion for how to improve everyone else’s.

On Washington

Madison first met George Washington in the winter of 1781–1782.

Yorktown had already been won.

The British were effectively beaten.

But wars are funny that way.

Winning on the battlefield and actually ending the conflict are not always the same thing.

Washington came to Philadelphia to coordinate the war’s final stages and discuss what came next.

Madison was there as a young member of Congress.

And the two men clicked almost immediately.

Which isn’t particularly surprising.

Because they brought completely different strengths to the table.

Washington had stature.

Gravitas.

Legitimacy.

When Washington entered a room, people paid attention.

Madison brought something different.

He understood details.

Strategy.

Procedure.

And perhaps most importantly, how to turn ideas into actual votes before anyone else realized the votes needed counting.

Together, they were surprisingly effective.

In fact, Madison became so useful that he occasionally drifted into territory that was almost comical.

At times, he would help Congress articulate its position on an issue.

Then turn around and help Washington draft a response.

Meaning Madison was sometimes writing letters to himself without technically writing letters to himself.

The OG ghostwriter.⁵Or perhaps the eighteenth-century version of ChatGPT. 😜

What Washington valued most was Madison’s ability to get things done.

Madison lobbied, built coalitions, tracked support, and counted votes.

And perhaps most importantly, he understood how to translate broad goals into actual legislation.

Washington trusted him.

A lot.

So much so that Madison eventually helped draft Washington’s first inaugural address and even worked on an early version of his farewell address.

Not everybody was thrilled about this arrangement.

Some politicians became openly jealous of Madison’s access to the president.

One senator complained that Madison was deeply involved in Washington’s business and worried that the people surrounding the president were becoming too influential.

A tale as old as politics itself.

Who has access matters.

Who influences power matters.

And Madison had both.

For a while, the relationship thrived.

In 1792, one of Madison’s most important political projects was convincing Washington to seek a second term.

The country was still fragile.

Washington remained uniquely trusted.

Madison believed America needed him.

So he got to work lobbying, persuading, building support, and doing all the behind-the-scenes things Madison did best.

And Washington stayed.

But by this point, something else was happening.

Political parties were beginning to emerge.

Lines were being drawn.

And Madison increasingly found himself standing closer to Jefferson than to Washington.

The friendship didn’t collapse overnight.

It eroded one disagreement at a time.

First came the Whiskey Rebellion.

When farmers in western Pennsylvania violently resisted a federal whiskey tax, Washington viewed it as a direct challenge to the authority of the national government.

And given everything Madison had just spent years building, you might think he’d feel the same way.

But Madison grew increasingly uneasy with how aggressively the administration responded.

Not because he supported rebellion.

But because he remained deeply suspicious of concentrated federal power.

Then came an even bigger fight.

The Jay Treaty.

A diplomatic agreement with Great Britain that was designed to avoid another war and resolve lingering disputes left over from the Revolution.

Washington supported it.

Hamilton supported it.

Madison did not.

Jefferson absolutely did not.

To Madison, the treaty felt far too accommodating toward Britain and far too dismissive of France, which many Americans still viewed as a revolutionary ally.

And unlike some earlier disagreements, this wasn’t a difference in style or strategy.

This was a genuine disagreement about the country’s future.

Madison opposed the treaty publicly.

Washington supported it publicly.

Neither man changed his mind.

And for perhaps the first time, their political differences proved stronger than their personal relationship.

The result was painful.

The letters stopped.

The visits stopped.

The friendship stopped.

And just like that, one of the most important political partnerships of the founding era was over.

And in a twist that feels very Madison, even some of his own allies thought he hadn’t pushed hard enough against Washington.

So by the end, Madison had somehow managed to frustrate Washington while also disappointing some of his own allies.

Which, as we’re going to see, became one of the occupational hazards of being America’s first politician.

On Jefferson

If Washington gave Madison a front-row seat to power, Jefferson gave him something different.

A collaborator.

A confidant.

A political partner.

The two men first worked together when Jefferson served as governor of Virginia and Madison was a young member of the Governor’s Council.

They would cross paths again in Congress.

And over time, one of the most important friendships in American political history began to take shape.

On paper, they had a lot in common.

Both Virginians.

Both devoted to religious liberty.

Both deeply skeptical of concentrated political power.

Both absolutely incapable of solving a problem without first writing fiftyleven words about it.

But their similarities only tell part of the story.

What made the partnership work was oftentimes their differences.

Jefferson was eight years older.

More famous.

More charismatic.

More ideological.

Jefferson loved big ideas, grand theories, elegant principles, and waxing philosophical.

Madison loved systems, details, and practicalities.

If Jefferson wanted to know how far freedom could be stretched, Madison wanted to know where it might snap.

Again and again, Jefferson would push toward an ideal.

And Madison would gently test it.

Refine it.

Challenge it.

Strengthen it.

Not by dominating the conversation.

But by helping Jefferson think more clearly.

The biographer repeatedly describes Madison as a moderating influence.

More practical.

More temperate.

Less likely to sprint headfirst into an ideological brick wall.

Which meant Jefferson often treated him less like a subordinate and more like an adviser.

Someone whose judgment he genuinely valued.

And perhaps most importantly:

Someone he trusted.

Jefferson frequently praised Madison’s good sense, sound judgment, and loyalty.

A combination he did not hand out casually.

Now, the biographer also suggests something else that may have been just as important.

Jefferson may not have viewed Madison as a threat.

Because if there’s one recurring theme in these early presidential biographies, it’s that powerful men tend to prefer talented friends who are not actively competing for their jobs.

Fortunately for Jefferson, Madison seemed perfectly comfortable operating behind the scenes.

In some ways, he reminds me of the Wizard of Oz.

Not because he was secretly controlling events.

But because he was often standing behind the curtain helping shape them.

Offering advice.

Testing arguments.

Building coalitions.

Helping turn ideas into reality.

And those who know me know this is EXACTLY the role I thrive in.

And he wasn’t just doing this for Jefferson.

Madison spent much of his political career helping other people turn ideas into action.

Which may explain why he occasionally feels less visible than some of his contemporaries despite being involved in nearly everything.

One thing that also jumps out from their correspondence is how differently they thought about writing itself.

Jefferson became increasingly cautious.

Years of political controversy had taught him that letters had a nasty habit of escaping into the wild and causing problems.⁶ You can read ALL about that in my Jefferson post.

Madison took the opposite approach.

He wrote constantly.

Not because he loved writing for its own sake, but because writing was how he worked through ideas.

If Madison had a love language, it was editing.

Even when sick, the man simply refused to stop writing.

During one bout of dysentery around the election of 1800, he somehow produced a twenty-thousand-word defense of the Virginia Resolutions.

🗣️ TWENTY 🗣️THOUSAND

Words.

The dynamic between Madison and Jefferson became especially clear during the fallout from Thomas Paine’s book Rights of Man.

When John Adams got irate about comments Jefferson had attached to the book, it was Madison who jumped into the fight.⁷ Yet another example of Jefferson’s leaky letters. Again I say, read my Jefferson post!

Jefferson may have thrown the punch.

But Madison was standing in the corner wrapping his hands beforehand and yelling encouragement afterward.

As one historian put it, Jefferson struck the blow.

Madison primed him, defended him, and congratulated him.

Which honestly feels like a pretty accurate summary of their relationship.

For decades, the partnership endured.

Political allies.

Friends.

Co-conspirators in the great project of arguing with Federalists.

And when both men got old, their final letters to one another reflected just how much the relationship had meant to them both.

Jefferson wrote:

“The friendship which has subsisted between us, now half a century…”

and described Madison as a pillar of support throughout his life.

Madison responded that he looked back on their long friendship and political harmony with equal affection.

It’s a surprisingly sweet ending.

Because by then they had helped build political parties, shape governments, survive controversies, win elections, lose elections, and fundamentally alter the course of American history.

Together.

And unlike Madison’s friendship with Washington, this one lasted.

Secretary of State

Now, in perhaps the most Madison moment imaginable, he wasn’t even present for Jefferson’s inauguration.

The reason?

Rheumatism. Which is basically like arthritis.

I mean, the man helped build the government, helped elect the president, helped shape the political movement that won the election…

…and then missed the ceremony because he was sick. 😫

But by the time Jefferson became president, Madison wasn’t just a trusted adviser.

That story had already been written.

Now he had a title.

Secretary of State.

And with it came a new challenge:

Figuring out how to be both Jefferson’s right hand and his own political figure at the same time.

Fortunately, he walked into one of the strongest political teams in early American history.

💅🏾 Jefferson.

🔥 Madison.

🏆 Gallatin.⁸ I know y’all don’t know who this man is, but you get the point. Just stay with me.

And unlike Washington’s cabinet, where half the job seemed to involve refereeing Hamilton and Jefferson, this group actually liked each other.

They shared goals, assumptions, enemies, and perhaps most importantly, trust.

And that trust wasn’t accidental.

Part of it came from something we already discussed:

Neither man saw the other as a threat.

Which is impressive when you consider that everyone understood Madison was the likely successor.

The heir apparent.

And that visibility came with consequences.

Because while Madison’s influence was undeniable, he didn’t enjoy the protection that came with being president.

Some critics accused him of being detached and unwilling to get his hands dirty.

Others accused him of being too political.

Still others accused him of selling out the movement altogether.

Which is a fascinating combination of complaints.

Apparently Madison was simultaneously too pure, too corrupt, too passive, and too influential.

The man was collecting criticism like Pokémon cards.⁹ Here comes the Pokémon cards again. And again I refuse to learn about them, to the frustration of my kids. Ooo, but did you know there’s a similar card collecting game called Gaiaton but instead of Pokémon, each card is a different animal? Anyway, Chile, let me get back to this blog. But go Google them!

Meanwhile, Madison’s actual job involved handling America’s relationship with the rest of the world.

Which would have been easier if the rest of the world had been behaving.

It was not.

The Europeans were once again outside acting up.

Britain and France were fighting.

Spain’s empire was wobbling.

And Madison kept getting handed an endless stream of international headaches involving trade, territory, Florida, Louisiana, and Britain’s extremely rude habit of stopping American ships and kidnapping sailors for its navy.

And Madison was in the middle of all of it.

Just spinning in circles trying to keep up.

Now, while much of the Louisiana Purchase story belongs to Jefferson, let’s not act like Madison was sitting quietly at his desk eating snacks.

He was right there helping navigate the negotiations, the backroom conversations, and all the political maneuvering that helped double the size of the country.

Then came the embargo.

Now, if you read my Jefferson post, you already know how this story ends.

Spoiler alert:

Not well.

But here’s the thing…

The embargo was largely Madison’s idea.

Yes.

THIS James Madison.

The careful planner.

The details guy.

Madison believed America could use its economic power instead of military power.

Rather than sending soldiers into another conflict, the United States would stop trading with Britain and France.

On paper?

Pretty clever.

Europe depended on American goods.

America would cut off trade.

Britain and France would feel the pain.

Everyone would come back to the negotiating table.

War avoided.

Problem solved.

In reality?

Britain and France basically looked at America’s master plan and said:

Meanwhile Americans were out here losing money, losing markets, smuggling goods, and getting increasingly irritated.

The economy suffered, smuggling exploded, and people got angry.

And before long, what was supposed to be a strategic flex started looking more like a self-inflicted wound.

As criticism mounted, Madison kept defending the policy in a series of anonymous newspaper essays.

Because of course he did.

The man never met a political controversy he couldn’t respond to with more writing.

But this is where things get interesting.

Because unlike Jefferson, who was approaching retirement and increasingly retreating from public battles, Madison couldn’t simply walk away.

This was his policy.

And suddenly Madison had to live with Madison’s ideas.

At exactly the same moment another challenge was emerging:

The presidency.

Most people assumed Madison would eventually succeed Jefferson.

But assumptions aren’t elections.

His biggest challenge came from within his own party.

James Monroe.

A fellow Virginian.

A Jefferson ally.

A proven political heavyweight.

And, importantly, someone who was not associated with the embargo.

Madison needed to defeat Monroe.

But not destroy him.

They belonged to the same political family.

Jefferson cared about both men.

And everyone involved understood they would likely need one another again.

Which meant Madison had to perform one of his favorite political tricks:

Win the argument while preserving the relationship.

Fortunately, he had help.

Gallatin rallied support.

Jefferson quietly backed him.

And Dolley Madison proved herself to be one of the most effective political assets in America, charming allies and building goodwill everywhere she went.

Which feels like as good a time as any to introduce Dolley.

Madison had married Dolley Payne Todd in 1794, and over the years she became every bit as politically skilled as her husband—just in a very different way.

While James Madison was busy building coalitions, counting votes, and generally being America’s most influential paperwork enthusiast, Dolley was handling the people.

She was warm.

Social.

Memorable.

The kind of person who could walk into a room full of political rivals and leave with half of them liking her.

And in an era when politics often happened over dinners, receptions, visits, and informal gatherings, that mattered a lot.

Madison and Dolley made a surprisingly effective team.

He worked the policy.

She worked the room.

He built coalitions on paper.

She built them in person.

By the time Madison began his run for the presidency, Dolley had already become one of the most recognizable political figures in the country in her own right.

Which is impressive considering women couldn’t vote, hold office, or formally participate in most of the political system.

Yet somehow Dolley still became one of its most important players.

And trust me.

We will absolutely be talking about her again.

By 1808, Madison had done it.

He won the presidency.

At long last, the man behind the curtain was stepping onto center stage.

Unfortunately, the timing could not have been worse.

Because he inherited a divided party, an angry opposition, a deeply unpopular embargo, and a world war that was becoming increasingly difficult to avoid.

In other words:

Madison finally got the job.

And almost immediately discovered why nobody should’ve wanted it.

The President

The Job He’d Been Preparing For

For most of his life, James Madison had been the guy behind the curtain.

The adviser.

The strategist.

The coalition builder.

The man helping other people run things.

Now it was finally his turn.

With a vice president by the name of George Clinton.

Not of Parliament-Funkadelic fame.

Different George Clinton.

And almost immediately, things started going sideways.

Madison entered the presidency with a fairly clear set of principles.

He believed in limited government.

Fiscal responsibility.

Following the Constitution even when it was inconvenient.

Peace whenever possible.

In short, Madison wanted a government that was efficient, restrained, and relatively inexpensive.

Unfortunately, the world had other plans.

Because before Madison could even start worrying about Britain and France, he ran headfirst into a problem much closer to home:

People.

Specifically, the people working for him.

One of Madison’s first headaches involved his cabinet.

He wanted to move his trusted ally Albert Gallatin into the position of Secretary of State.

The Senate said:

Absolutely not.

So Madison ended up appointing Robert Smith instead.

A decision he would spend years regretting.

And here’s where we begin seeing one of Madison’s recurring weaknesses as a leader.

He hated confrontation.

Loved persuasion.

Loved compromise.

Loved patiently bringing people around to his way of thinking.

But firing someone?

Making a clean break?

Looking a grown man in the eye and saying:

“Sir, respectfully, you’re terrible at this.”

Not his favorite activity.

So instead of replacing Smith immediately, Madison spent years quietly covering for him.

Fixing mistakes.

Cleaning up messes.

The presidential equivalent of covering your coworker’s shift while complaining about them the entire time.

Eventually Madison snapped.

And because he was James Madison, he documented the entire thing.

In writing.

I mean, is anyone surprised?

At one point he complained that Smith’s letters were so bad he routinely had to rewrite them himself.

And what’s even more frustrating?

Madison knew Smith wasn’t the right choice.

He had known it for years.

But he kept avoiding the fight.

And now he was paying for it.

As we will soon see, this would not be the last time reality punished Madison for avoiding unpleasant conversations.

---

The War Nobody Really Wanted

One of the stranger things about Madison’s presidency is that he spent years helping create many of the problems he would eventually inherit.

By the time he took office, the international situation was already a mess.

Britain and France were still fighting.

American ships were still getting caught in the middle.

Trade was still a disaster.

And nobody seemed particularly interested in respecting American neutrality.

Meanwhile, the embargo had collapsed under the weight of its own unpopularity.

Which presented Madison with an awkward problem.

Because while the policy belonged to Jefferson’s administration…

it also kind of belonged to Madison.

And now he was president.

Meaning there was no longer anyone else to hide behind.

For years Madison had argued that economic pressure could accomplish what war could not.

Now he had to figure out what came next after economic pressure failed.

And for a while, he kept searching for another off-ramp.

Another letter.

Another meeting.

Another attempt to talk this thing to death before somebody started shooting.

Because despite everything that would happen later, Madison did not strike me as someone eager for war.

He was a systems guy.

A process guy.

A “surely we can all be reasonable here” guy.

The problem was that Britain seemed committed to proving otherwise.

And as the frustrations piled up, Madison found himself facing a question he had spent years trying to avoid:

What do you do when the meetings aren’t working?

When the negotiations aren’t working?

When talking it through isn’t working?

When every off-ramp leads right back to the same problem?

Unfortunately, the answer was beginning to look a lot like war.

---

National Respect and the Road to War

The deeper problem wasn’t really trade.

It was respect.

Or more specifically:

The growing feeling that the United States wasn’t getting any.

Britain repeatedly interfered with American shipping.

Ignored American complaints.

Stopped American vessels.

And forcibly took sailors into the British navy.

Which is a very polite historical way of saying:

Britain was out here kidnapping people.

Now, were there complicated legal arguments involved?

Sure.

There always are.

But for many Americans, the issue felt much simpler than that.

The United States had fought an entire revolution to stop being treated like a subordinate.

And yet Britain still seemed determined to treat America like its annoying little sibling.

Eventually a growing number of Americans reached the same conclusion:

If the country wanted respect, it was going to have to demand it.

Because at some point the conversation stopped being:

“How do we solve this?”

And started becoming:

“How much longer are we supposed to put up with this?”

National pride.

National dignity.

National self-respect.

Madison wasn’t looking for war.

But he was increasingly running out of ways to avoid it.

And in June 1812, Congress declared war on Great Britain.

The narrowest vote for a declaration of war in American history.

Which probably should have been everyone’s first clue that this was not going to be a smooth operation.

---

Reality Arrives

Because here’s the thing.

America wasn’t really prepared for war.

The military? Small.

Finances? Shaky.

The administration? Understaffed.

The national bank? Gone.

And if you’re wondering how America ended up entering a war without a national bank?

Well…

Years earlier, Madison had joined Jefferson in opposing Alexander Hamilton’s national bank, arguing that the Constitution didn’t explicitly give Congress the power to create one.

And congratulations, Madison! Those arguments worked!

The bank’s charter expired in 1811 and wasn’t renewed.

Which meant that when war arrived, one of the country’s most useful financial tools was sitting on the sidelines.

Essentially, Madison’s younger self came back from the grave and voted against him.

And Britain was, inconveniently, one of the most powerful military forces on Earth.

It was basically the geopolitical equivalent of talking trash online and then discovering the other person actually knows how to fight.

Madison seems to have believed Britain was too busy fighting Napoleon to devote serious attention to America.

But unfortunately for him, Britain proved capable of multitasking.

And before long, things started going real bad.

Then, from bad to worse.

Then somehow even worse than that.

Meanwhile, Madison’s health was doing what Madison’s health often did.

Causing problems.

The man seemed to collect illnesses the way other people collect hobbies.

Bilious fever left him bedridden for weeks.

And despite all of this?

He kept working.

Kept writing.

Kept governing.

Which makes me think Madison viewed illness less as a reason to stop working and more as a recommendation to work from bed.

---

Well, This Is Bad 🔥

Then came 1814.

And everything caught fire.

Literally. 🤣

British forces marched into Washington.

Government officials fled.

Chaos spread.

And before long, the British set fire to the Capitol, the White House, and several other government buildings.

This remains one of the most embarrassing chapters in presidential history.

Imagine spending decades helping build a government.

Then watching someone burn down the buildings.

Madison found himself fleeing the capital.

Which can’t be the proudest of moments for a president.

But freeze frame it right here. Because this is where Dolley once again saves the day.¹⁰ See? I told you she would make another appearance.

Because while everybody else was scrambling, Dolley Madison was busy securing important government papers and helping save Gilbert Stuart’s famous portrait of George Washington.

And let me just say:

If there is one thing America’s First Ladies know how to do, it’s save the republic while the men are outside creating avoidable problems.

The British burned the city.

But they didn’t break the country.

And perhaps surprisingly, they didn’t break Madison either.

---

Learning on the Job

One thing about Madison as president? He’s actually pretty good at learning from his mistakes.

Which sounds like a low bar.

But history suggests it is not.

Madison replaced ineffective officials, listened to stronger advisers, improved military leadership, and gradually got better.

And by the later years of the war, the administration looked much more competent than it had at the beginning.

Madison was never going to be America’s most charismatic president.

But he may have been one of its most teachable.

---

The Weirdest Win

The War of 1812 ended with the Treaty of Ghent.

And here’s the funny part.

The treaty basically restored things to where they had been before the war.

No major territorial gains.

No decisive military victory.

No dramatic triumph.

Which sounds suspiciously like a draw.

And yet Americans celebrated.

Why?

Because the point had gradually changed.

At the beginning, many Americans wanted Britain to respect the United States.

By the end, simply surviving the conflict felt like proof that the country had arrived.

The United States had gone to war against the world’s strongest power.

And it had not been crushed.

That mattered.

In a strange way, America won by proving it could take a punch and stay standing.

Which is not the most glamorous definition of victory.

But it counts.

---

One Last Madison Moment

And because Madison remained Madison until the very end, we have to talk about roads.

Specifically, roads and canals.

Madison believed the country needed better infrastructure.

Most people agreed.

Congress finally passed a bill to fund internal improvements.

Roads.

Canals.

Infrastructure.

Exactly the sort of thing Madison had spent years arguing America needed.

And then Madison vetoed it.

I know.

Stay with me.

He didn’t veto it because he opposed roads.

He vetoed it because he believed the Constitution didn’t authorize Congress to fund them directly.

In his view, the country needed a constitutional amendment first.

And if that sounds frustratingly technical, welcome to James Madison!! 😁

The man spent his entire life believing process mattered.

Even when the outcome was something he wanted.

By the time he left office, Madison had helped write the Constitution, defend the Constitution, interpret the Constitution, fight a war under the Constitution, and veto legislation because of the Constitution.

Nobody can ever accuse this man of not committing to the bit.

And honestly?

That’s probably the most Madison ending imaginable.

On Slavery

Welp.

Here we are again.

Because these Founding Fathers love to talk about liberty but want to go mute when somebody asks, “Liberty for who, exactly?”

For what it’s worth, Madison appeared unusually aware of the contradiction.

He understood the problem.

He understood the hypocrisy.

He understood the tension between a nation founded on liberty and a society built on slavery.

But, the issue is that understanding a contradiction and resolving said contradiction are two very different things.

And Madison spent most of his life doing the former.

So, my frustration with Jefferson was primarily his hypocrisy, while my frustration with Madison was his awareness.

Let’s start with one of the biggest examples.

SIGH.

Madison helped create the Three-Fifths Compromise.

Now, if you’re anything like me, you probably learned the term Three-Fifths Compromise in school and immediately filed it under:

“Not good.”

And/or remember it as being about enslaved people only counting as three-fifths of a person. Which…is an understandable takeaway, but not exactly it.

So let’s talk about what it actually is.

When delegates gathered to write the Constitution, they had a problem.

How would states be represented in Congress?

Southern states wanted enslaved people counted when determining representation.

Northern states pointed out a rather obvious problem:

If enslaved people were property, why should they count toward political power?

Southern states essentially wanted the political benefits of counting enslaved people without granting enslaved people any rights.

And the compromise that emerged counted enslaved people as three-fifths of a person for purposes of representation.

Madison helped develop the framework behind that agreement.

The result gave slaveholding states additional political power while ensuring enslaved people themselves received none of the benefits.

And that contradiction would become yet another ghost hanging over American politics for generations.

Because one thing slavery repeatedly demonstrates is that people can become very creative when trying to reconcile the irreconcilable.

Madison spent much of his political career doing exactly that.

In public, he often tried to avoid the slavery question altogether.

Partly because he believed it distracted from other political goals.

Partly because he knew how explosive it was.

And partly because he understood the trap.

How could the self-proclaimed champions of liberty explain holding other human beings in bondage?

The answer, unfortunately, was usually:

By changing the subject.

And people absolutely noticed.

One critic mocked Virginia politicians for “whipping negroes” while simultaneously lecturing the world about the inalienable rights of man.

Even Lafayette eventually pressed Madison on the issue.

Because apparently America’s favorite Frenchman spent his retirement years traveling around asking people uncomfortable questions.

Respect.

But Madison never stopped wrestling with the contradiction.

The problem is that his solutions increasingly sounded like attempts to solve slavery without actually confronting slavery.

By retirement, Madison had developed three major ideas.

And before I tell you what those ideas were, let me save us all some suspense:

None of them involved freeing his own enslaved people.

First came diffusion.

Madison believed slavery could gradually weaken if it spread across a larger geographic area.

Instead of remaining concentrated in certain regions, enslaved people would be dispersed across the expanding western territories.

In Madison’s view, this would reduce the density of slavery, expose enslaved people to larger free populations, and eventually encourage manumission.

To which I say…😒

Sir.

The problem is still slavery.

And slavery doesn’t become freedom simply because there is less of it per square mile.

Second came colonization.

Which was exactly what it sounds like.

Madison imagined a massive national effort to purchase enslaved people and resettle them in Africa.

Specifically Liberia.

He even ran the numbers.

Which feels incredibly on brand.

Because of course James Madison made a spreadsheet for ending slavery.

The proposal was enormous.

Expensive.

Complicated.

And built on an assumption that freed Black Americans belonged somewhere other than the United States.

Which is yet another sticking point for me.

Because both diffusion and colonization share the same underlying premise.

The solution is not Black people being free where they already are.

The solution is Black people being somewhere else.

West.

Africa.

Anywhere but here.

The third possibility arrived in the form of a younger man named Edward Coles, who was a relative of Dolley’s.

Now, Coles did something pretty remarkable.

He took the people he enslaved to Illinois and freed them.

With papers. And land.

You know, actual freedom.

And when he wrote to Madison to tell him about it, Madison praised and congratulated him.

Expressed his admiration for him.

And then…

went about his business without following the example himself.

And that’s the story of Madison and slavery in a nutshell.

Over and over again Madison would prove he could recognize the morality of an action without ever taking it himself.

The biographer spends considerable time describing Madison’s sadness over slavery during retirement.

Visitors reported hearing him lament the institution.

He spoke of its immorality.

Its injustice.

Its incompatibility with American ideals.

At one point he reportedly observed that the Bible opposed slavery but ministers failed to preach it.

At another point he admitted he felt almost despair about the issue.

And I know the biographer wants me to feel something here.

Sympathy, perhaps.

Understanding.

Well…

Because my thing is…

Madison wasn’t some random observer watching history happen from the sidelines.

He was 👏🏾 James 👏🏾 Madison.

Architect of the Constitution.

Former president.

One of the most influential political figures in American history.

And yet when it came to slavery, his ultimate response looked remarkably similar to Jefferson’s.

More concern.

More proposals.

More ideas.

More waiting.

And ultimately?

More inaction.

Madison died in 1836.

He did not free the people he enslaved in his will.

Not a one.

His final hope remained colonization and Liberia.

But the numbers tell the story.

Over nearly twenty years, the American Colonization Society had resettled fewer than three thousand people.

Meanwhile, America’s enslaved population was increasing by tens of thousands every year.

The math was never close.

Which leaves me with the same frustration I felt throughout much of Madison’s life.

The man could identify problems.

Analyze problems.

Debate problems.

Design systems around problems.

But when it came to slavery, he never managed to do the one thing that mattered most.

Act.

The Legacy

If Jefferson was America’s philosopher…

Madison may have been America’s first politician.

And I don’t mean that in a bad way.

At least not entirely. 👀

Because Madison seemed less interested in winning every individual argument than in building systems that could survive disagreement.

Which sounds less exciting than writing the Declaration of Independence.

And it is.

But it’s also incredibly important.

Declarations are easy.

Governing is hard.

Madison understood something that many revolutionaries throughout history eventually discover:

Winning independence and maintaining a functioning government are not the same thing.

And for most of his life, he was obsessed with that second question.

How do you build a system strong enough to survive conflict without becoming a threat to liberty itself?

How do you create a government capable of acting without creating a government capable of dominating?

How do you preserve freedom while still preserving order?

Those questions never really left him.

In many ways, they defined his entire career.

And they help explain one of the most interesting questions in Madison’s legacy.

Madison spent much of his life building a system designed to limit power.

Which sounds great.

Until somebody hands you a war.

Then things get complicated.

Because one of the questions Madison’s presidency raises is whether the same qualities that make someone an excellent constitutional thinker necessarily make them an excellent wartime leader.

Madison spent years trying to balance individual liberty against national security.

Personal freedom against governmental power.

Principle against practicality.

And unlike some presidents who eagerly grabbed additional authority during crises, Madison remained remarkably cautious.

Sometimes admirably so.

Sometimes frustratingly so.

Depending on your perspective.

Reading about his presidency, I kept finding myself asking:

Do we want a president who strictly follows his principles during difficult moments?

Or do we want a president who is willing to bend those principles to get results?

Madison’s answer was usually pretty clear.

The rules still mattered.

Especially when they were inconvenient.

Which is probably why he spent his final days still arguing about constitutional questions.

The man never stopped being himself.

Ever.

In retirement, Madison became increasingly focused on how future generations would understand the founding era.

And because he was James Madison, he had receipts.

Specifically:

Those notes.

So many notes.

Throughout his life, Madison had carefully documented the debates of the Constitutional Convention.

But he refused to publish them.

Not immediately.

Not while the participants were still alive.

Not while people could argue back.

Which is either an act of historical stewardship or the pettiest long game in American political history.

Possibly both.

Madison understood something important.

The longer he waited, the more influential those notes would become.

And once everyone else was gone?

Well.

Nobody could interrupt the narrative, contradict him, or challenge his version of events.

The man was determined to get the last word.

And kudos to you, Sir.

Because those notes would eventually become one of the most important sources we have about the Constitutional Convention.

Not because Madison created the Constitution alone.

He didn’t.

One thing his notes reveal is that the founding generation was not a room full of geniuses calmly agreeing with one another.

It was a room full of strong personalities arguing constantly.

Compromising.

Changing positions.

Building coalitions.

Losing votes.

Winning votes.

And somehow creating a government in the process.

Which brings me back to why I keep calling Madison America’s first politician.

Not because he was the first person to seek power.

Not because he was the first person to compromise.

But because he understood the machinery of politics itself.

Parties.

Coalitions.

Public opinion.

Legislative strategy.

The delicate art of acquiring, sharing, restraining, and occasionally surviving power.

Again and again throughout his life, Madison demonstrated a skill that would become essential to American politics.

He knew how to build alliances.

He knew how to keep them together.

And perhaps most importantly, he knew how to lose an argument without leaving the game.

That may not sound glamorous.

But constitutional government depends on people being willing to do exactly that.

For all his flaws, Madison understood that.

What I’m less certain about is whether those same qualities always translated into effective executive leadership.

Because being a politician and being a president are not necessarily the same job.

Madison excelled at persuasion, coalition building, legislative strategy, and helping groups of people find enough common ground to move forward.

But presidents don’t always get the luxury of operating behind the scenes.

Sometimes they have to make decisions before all the information is available.

Sometimes they have to fire people.

Sometimes they have to act before consensus exists.

Sometimes they have to stop studying the problem and choose.

And so I found myself wondering whether Madison’s greatest strengths occasionally became his greatest weaknesses.

The same caution that made him a thoughtful constitutional thinker could make him hesitant.

The same respect for process that made him a careful politician could make him slow to act.

The same ability to see multiple sides of an issue could make decisive leadership more difficult.

Which isn’t necessarily a criticism.

It’s just the tradeoff.

The qualities that made Madison brilliant at building the system did not always make him brilliant at running it.

That’s part of what makes him so interesting.

And perhaps that’s why his influence still feels so present.

Not because Americans spend much time thinking about James Madison.

Let’s be honest.

Most of us don’t.

But because we still live inside many of the systems he helped create.

The Constitution.

The Bill of Rights.

Political parties.

Congressional politics.

The constant tension between liberty and authority.

His fingerprints are everywhere.

Even when his name isn’t.

Which is probably exactly how he liked it.

And fittingly, Madison’s final recorded words may be the most Madison thing imaginable.

When asked what was wrong, he reportedly replied:

“Nothing more than a change of mind, my dear.”

An intellectual to the very end.

A man still revising.

Still reconsidering.

Still thinking.

Still changing his mind.

Honestly?

A pretty fitting ending for the architect who never quite stopped revising the blueprint.

Random, Interesting Facts

Even though Madison spent most of his life trying to solve America, he did occasionally have interests outside of politics.

Key word here: Occasionally.

First: Madison got his heart broken.

Yes.

James Madison.

Future President of the United States.

Father of the Constitution.

Architect of the Bill of Rights.

Got dumped.

In 1783, Madison fell for Catherine “Kitty” Floyd, the teenage daughter of a New York congressman whose family happened to be staying in the same Philadelphia boardinghouse.

The courtship lasted several months.

And then Kitty married someone else.

Specifically, a medical student much closer to her own age.

Which, you can’t really fault the girl for.

But still.

Madison was apparently devastated.

And in one of history’s more unexpected friendship moments, the person helping him through the heartbreak was Thomas Jefferson.

At the time, Jefferson was grieving the death of his wife, Martha.

So apparently one of the earliest bonding experiences in the Madison-Jefferson friendship was sitting around processing romantic disappointment together.

And speaking of romance…

---

Second: We have Aaron Burr to thank for Madison meeting Dolley.

I know.

We just can’t escape him.

At the time, Burr was handling some legal matters for Dolley Todd, a young widow living in Philadelphia.

He formally introduced her to Madison.

And for once in his life, Aaron Burr’s involvement in a historical event produced something wholesome.

Madison and Dolley married in 1794 and went on to become one of the most successful political partnerships in American history.

So I guess we have to give Burr partial credit for that one.

Just that one.

---

Third: Madison accidentally helped give us the National Anthem.

Sort of.

During the War of 1812, a Georgetown lawyer named Francis Scott Key traveled to Baltimore to negotiate the release of an American prisoner.

While there, he witnessed the British bombardment of Fort McHenry from a ship in the harbor.

Watching the American flag remain standing through the attack inspired him to write a poem called Defence of Fort M’Henry.

That poem eventually became:

🎵 The Star-Spangled Banner. 🎵

Which means Madison’s presidency gave us both a war and the song we still sing about it.

A very efficient use of a historical crisis.

And finally:

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Madison’s presidency gave America its first inaugural ball.

Which feels appropriate.

Because after spending years worrying about the future of the republic, the man finally got an excuse to attend a party thrown specifically for him.

Whether he actually enjoyed it is another question entirely.

This is James Madison we’re talking about.

So, while Dolley was out here being the Hostess with the Mostest, Madison probably spent half the evening mentally revising a draft of something.

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 Madison…

Fave Ranking: #4

I know.

I KNOW.

Put your pitchforks down.

Here’s the thing:

Madison is one of the most important people we’ve covered so far.

He is also, at times, the human embodiment of unsalted grits.¹¹And if you put sugar in your grits…are you okay?

Washington gave me action hero energy.

Adams gave me petty king energy.

Jefferson gave me enough contradictions to fuel an entire book club.

Madison gave me…

thoughts.

Carefully organized thoughts.

Revised thoughts.

Footnoted thoughts.

At one point I genuinely felt like I was reading the biography of a very gifted spreadsheet.

Now, don’t get me wrong.

Had we met in real life?

We probably would’ve been friends.

We could have sat around debating politics, philosophy, and public policy until somebody politely asked us to leave the bar.

But reading about him?

Ain’t it.

Respectfully.

So he lands at #4.

For now.

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Presidential Ranking: #2

Okay.

Now THIS is where people are really going to start arguing with me.

Because I actually think Madison edges out Jefferson here.

Barely.

And I do mean barely.

Washington still holds the top spot. Nobody has come close to knocking him off the throne yet.

But Madison does get second.

Because while Jefferson accomplished some enormous things, Madison spent years helping make many of those accomplishments possible in the first place.

And then, when it was his turn?

He inherited a divided party, a foreign policy mess, a failing embargo, and an increasingly likely war with the world’s strongest military power.

Was everything handled perfectly?

Absolutely not.

Have we literally spent the last several thousand words discussing that?

Yes.

But the country survived.

The government survived.

The Constitution survived.

And America emerged with greater confidence than it had before.

I also have to give him credit for something Jefferson often struggled with:

Consistency.

For better or worse, Madison spent much of his career trying to live by the principles he claimed to believe in.

Sometimes to a fault.

Sometimes to the frustration of everyone around him.

Sometimes while I was actively yelling at the book.

But there was less of the:

“Limited government for thee but not for me.”

energy that occasionally popped up during Jefferson’s presidency.

So yes.

Madison gets second.

And Jefferson slides to third.

Please direct all complaints to the comments section.

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Impact Ranking: #3

And this is where my beloved Adams takes another loss.

Because Madison’s impact is impossible to ignore.

The Constitution.

The Federalist Papers.

The Bill of Rights.

The House of Representatives.

The entire framework of American government.

When Americans argue about free speech, religion, guns, privacy, due process, executive authority, states’ rights, federal power, and constitutional interpretation…

They’re often arguing inside systems Madison helped build.

In fact, there are moments when Madison’s work feels even more present in daily American life than Jefferson’s.

The Constitution isn’t just a historical document.

It’s still shaping political arguments every single day.

Still, Jefferson remains ahead of him here.

Because Jefferson’s footprint extends beyond government into America’s identity itself.

The Declaration of Independence.

The language of liberty.

The Louisiana Purchase.

The very story Americans tell themselves about who they are.

That’s hard to beat.

The Declaration of Independence tells us what America believes.

The Constitution tells us how America operates.

And Madison’s fingerprints are all over the second one.

So Madison lands at #3.

Ahead of Adams.

Behind Jefferson.

And honestly?

I suspect Adams would be absolutely furious about it.

Which somehow makes me feel a little better.

---

Now I fully expect some of y’all to disagree with me. Especially on that Presidential Ranking. So tell me:

Where do you have Madison?

Am I underrating him?

Overrating him?

Has my long-running Adams bias finally become a public health concern?

Let me know in the comments.

And because keeping track of these rankings is only going to get harder from here, don’t forget to check out the Presidential Rankings page.

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And with that, we leave behind America’s first politician.

The note-taking king.

The Constitution guy.

The man who somehow turned overthinking into a governing philosophy.

Next up:

James Monroe.

Last of the Founding Fathers to reach the presidency.

Sometimes referred to as “History’s Forrest Gump.”

War hero.

Diplomat.

Madison’s longtime ally.

And the man whose presidency would eventually become known as the “Era of Good Feelings.”

Which sounds suspicious.

Because if there’s one thing I’ve learned from this project, it’s that whenever historians give an era a name that cheerful, somebody is almost certainly about to start acting up.

See y’all soon.