Happy 269th Birthday, James Madison!

The Story of James Madison
2020 Edition By Corinne Waterstraut
Two-hundred and 69 years ago today (March 16), the future 4th president of the United States of America was born in the Virginia colony. James Madison, Jr. was a scrawny sickly kid, who grew up on his family’s tobacco farm. It wasn’t just any farm though. His parent’s were the largest land owners in all of Orange County. The families money allowed all the Madison kids (11 in all, but some of them died, you know, the 1700s) to study at elite schools with the best tutors.

James was a fan of schooling and reading, which was good because he was a sickly scrawny kid and couldn’t do much else. If you’re sick the 1700s, you’ve got to avoid outdoor activities. There’s so much out there that can kill you! And there’s no video games to play, so James buried his nose in good book after good book. Even doctors told him to lay off the reading, and studying. James, of course didn’t listen.

  By the time he was 11, he had read all 85 books in his dad’s library. He spent the rest of his free time acting as an amateur scientist,  dissecting rabbits and other small animals. By 16, he could read Plato and Aristotle in original Greek, when most people can barely understand Plato in English! Long story short, James Madison will always been a bookish soft spoken guy.

It’s often said James spoke so quietly, with a voice so low and weak, you can’t be heard at all. Reports and quotes by him leave words blank because you can’t hear what he’s saying a lot of the time. He was a wallflower born with his nose in a book.

Even off at college, which will eventually become Princeton, James Madison is excelling at his school work, but falling short on the debate team. If you’re the lacking stock of a debate club at an elite school, you’re kind of the bottom of the barrel as far as nerdiness goes. He wasn’t even good at insults, once trying to knock is opponent off kilter by calling him smelly. That’s the best James Madison could come up with.

The guy wasn’t a social butterfly. Instead, he kept his nose in a book, sleeping four hours a night and spending the rest of his time studying so he could graduate in two years. He’d end up in politics and a member of the Virginia state legislature. James would never have a job outside of politics.


By now, James is in his 20s, but more importantly, we’ve arrived at a pivotal moment in American History: it’s time for a Revolution! You can’t tax us without representation! The red coats are coming!

Sickly, nervous, shy, James who will look like a boy well into his 30s (the guy will top out at 5’4” and 100 pounds soaking wet, making him the smallest of all our presidents) is not exactly the stuff military men are made of. Name an ailment in the 1700s, and James had it: influenza, hemorrhoids, dysentery, rheumatism. He would never see battle, but he would joke he got a nose scar from “defending the country”. The scar, however, actually came from riding horseback in the cold and getting frostbite.

 Instead of leading troops across the Delaware, or holding the flag on the tip, James will stay in Virginia and help where he can, putting his mind to work, serving in the Virginia legislature, and working as a protégé to a little guy you might have heard of, the one, the only: Thomas Jefferson! TJ is impressed by Madison’s knowledge, and that’s something, coming from smarty pants TJ.

We know what happens next, America wins its independence and now we have to make a country! And those countries are going to need some documents, and James Madison will be just the guy to write them. In fact, James Madison’s resume is full of heavy hitting founding father type documents. If it made it into your history book (and the National Archives), Madison probably had a hand in crafting it. His early career reads of US history itself. Let’s just consider him the most famous author of all time.

At 35, James is now the youngest delegate to the Continental Convention. He’s a boy wonder, wise beyond his years, and a passionate US supporter. He believes the US can have great influence in the world.

He helps writing the Articles of Confederation (the pre-Constitution if you will, giving the states some kind of unity before we got it together), and now he was ready to contribute to the Constitution to the new nation. Madison exhaustively studied ancient and modern confederacies and comes to the Convention full of ideas.

 In fact, his “Virginia Plan” would be adopted as the basis for the Constitution, and even soft spoken James will debate  71 out of the 86 days at the Convention. He tells friends to pull on his coat tails if he goes on too long. James will become known as “The Father of the Constitution”. He’ll be one of only two presidents to sign the document (George Washington is the second of course).

Maybe it’s appropriate that James Madison, the guy who doesn’t even want to take too much credit for everything said the constitution wasn’t just his vision but “the work of many heads and many hands”, after all the first three words of the Constitution are “we the people”.

But not everyone is sold on the Constitution, so James Madison gets together with his buddies John Jay, and Alexander Hamilton and help draft the Federalist papers. Basically, it’s the greatest persuasive essay ever written. The Federalist papers are 85 points (articles) on why the states should approve (ratify) the Constitution. Madison knows we need a strong central government to stay united. But he also knows the ability for the government to tax people is going to be controversial.

Of course the Federalist Papers do their jobs, since you know, we have the Constitution. In fact, James Madison was also the only guy to think the actual process of writing the thing is important, and so he takes notes.  Madison’s notes turn out to be the only records we have of the whole process.

Madison doesn’t think the Constitution goes far enough though, and eventually he will make it his mission to add the Bill of Rights, or the first 10 amendments to the Constitution. You know, the reason you can be a shit head on Twitter, carry a gun, and can protest in front of the White House. That’s all because of James Madison! He convinces everyone in Congress yet again that the Bill of Rights is necessary.

James will go on to serve four terms as a member of the US House of Representatives, and write speeches for George Washington, including GW’s very first inaugural address. He’s also going to help TJ form the Democratic-Republican party.

Madison is 43 by now, and he’s got an impressive resume to stay the least. But, he still doesn’t have a wife. He does have his eye on someone: 26 year old Dolley Payne Todd. Dolley was born in North Carolina, into a Quaker family (who have a strict, religious, reserved, peaceful, egalitarian way of life). Because of their Quaker religion, the family deliberately avoids participation in the Revolutionary War, so they give up their slaves and move to Philly.

Her father John’s progressive policies and piety is basically rewarded with bankruptcy and humiliation, and within six years his business in Philly goes belly up, and the Quakers disown him for being irresponsible with money, and then he dies.

But Dolley keeps on keeping on, besides the Quakers kicked the family out, and that’s not so bad. Dolley was finally free to shake off the Quaker rules and never look back. She can be herself!

Dolley gets married to John Todd Jr. and they have two kids. But, now yellow fever is ravaging the country (it’s the coronavirus of its day!), and while people are fleeing Philly to avoid dying, John is an upstanding lawyer who is going to stay behind to offer his legal services to the dying and widowed. It turns out to be a death sentence for John, though, and the couple’s youngest son, William.

Dolley isn’t immune to the yellow fever, but she’s young and she recovers. So now she’s 25, widowed with one son, Payne (full name John Payne Todd), but at least she’s left with some money. Most people would let all of this get them down, but not sociable, bright, pretty Dolley.
She’s back at it looking for love again, and she’s a total catch! She makes a splash in society, and draws attention for her gregarious, kindly nature. If there is a flattering adjective for someone who is beloved by everyone they meet, it’s been written about Dolley. She’s husbandless, and she’s relying on legal and financial advice from a bunch of eligible guys who fly to her like a moth to a flame.
James Madison has heard about Dolley, and he’s intrigued. Turns out one of his buddies, Aaron Burr, knows Dolley and can totally introduce them. Now, Aaron Burr will eventually be Thomas Jefferson’s Vice President, kill Alexander Hamilton in a duel, and then be charged with treason. It’s very scandalous, and you can hear all about it during TJ’s birthday in April, but for now, Aaron Burr is just the New York Senator who is going to introduce Dolley and James.

James Madison is a smart guy, but he’s a guy who has been called “the most unsociable creature in existence”, who “seems incapable of smiling.”  His look is that of a guy who is on the way to a funeral. He always powdered his wig and tied it back, wearing black (worth noting: black PANTS! He’s the first president to trade in pantaloons for regular old pants).

Who knows if it was the brains or the pants that reeled Dolley in. Maybe it’s the whole opposite attracts thing. James is boring, not colorful, withdrawn, sickly, a poor public speaker who shies away from public appearances, and Dolley is anything but. The chatty extrovert Dolley marries the quiet reserved James and they have, by all accounts, a warm and successful marriage.


1801 will be a big year for James. His dad will die, and leave him his Montpellier estate. But, Thomas Jefferson will also be elected president and appoint James Madison as his Secretary of State.

Again, we’ll talk about TJ’s presidency in April, but there are a few important things for James Madison here. First of all, TJ is a widow, and so is Vice President Aaron Burr. So if TJ is going to have any parties at the White House, he’s going to need a hostess. Enter hostess with the mostess, Dolley Madison! She’ll be more than happy to organize your parties. She lives for this stuff, and quickly becomes a respected leader in DC society.

But at the White House, TJ and his Secretary of State James Madison are dealing with hostilities between Britain and France. And now, the antagonistic British navy will not stop harassing US ships. They’re looking for British deserters, but they also force American sailors into duty. It gets really ugly, and then there’s a nasty incident off the coast of Virginia killing 21 Americans.

TJ is held up in bed with migraines, and James is so weak with a fever he can barely make it into their office. But something must be done, but TJ does not want to go to war. So TJ and Madison come up with the Non-Intercourse Act, which later gets replaced by the Embargo Act (I guess because they had enough sense to realize this might make it into the history books, and “non-intercourse” is just a weird word).

Anyway, basically the US is going to suspend trade with all of Europe to stay out of it all. But, this is unwelcome news to a lot of Americans. Farmers export grain to Europe and northern merchants aren’t pleased either.

We’ve arrived at the 1808 election, which will see the Democratic-Republican (aka Jeffersonian)  face off against the Federalists.

Secretary of State is still seen as a stepping stone into the presidency, but it was even more so in the early days of the nation. So after 8 years in office, TJ is ready to retire to “my family, my books, and farm” where he can study and research at Monticello and he hand picks James Madison to take over for him. After all, TJ thinks James is “the greatest man in the world.” High praise coming from Thomas freaking Jefferson.

But it won’t be that easy, after the Aaron Burr debacle, TJ has a new Vice President: George Clinton. And Clinton also wants to be president. He’s got the resume for it. He’s been a member of the Continental Congress, President of the 1788 New York Constitutional Convention, a two decade long governor of New York, and Vice President to TJ after that whole Aaron Burr debacle.

In 1808, were going to select our nominees in a caucus of a bunch of Congressman who will meet to pick a president and a vice presidential nominee. (Remember, we’ve arrived at the package deal part in American history.)

Madison wants to push up that caucus date before the “Madison for President” loses steam and he loses the nomination. He’s like, lets do this wucik before George Clinton can amass any sort of support. And the Clinton guys have the very poor strategy of saying ‘well, that’s wildly unfair we’re boycotting the caucuses’. Madison wants to eliminate George Clinton as a factor in the general election, so they suggest Clinton should be Vice President.  And so, the Democratic-Republicans put James Madison on the ballot for president, and George Clinton on the ballot for Vice President.

Madison may suffer from health issues (he’s 57 now), he has scowling expressions and is bad at basic social skills like eye contact. But he’s extremely bright, he’s always the best informed person in any situation. He’s persuasive, and all convincing (remember the Federalist papers) and has an astute grasp of the problems of the nation, has studied human nature enough to have a good grasp on people. And he’s got Dolley, and people just love her.

 The Federalists need a nominee now too. Enter: Charles Cotesworth Pickney, a South Carolinian Statesman who had served in the Revolutionary War, had been a delegate to the Constitutional Convention, and Minister to France under George Washington.

Charles Cotesworth Pickney isn’t what you’d call a winner. In 1800, he was passed up for Vice President. In 1804, he lost the presidency to Thomas Jefferson in a landslide. The Federalists were pretty sure they didn’t even have a chance, so they threw Pickney in there just for fun.

In fact, the whole Pickney family is a bunch of losers. His brother was also a failed Vice Presidential Candidate, and his cousin General Charles Pinckney was a racist, arrogant asshole (For real, for awhile in my research I thought Charles Pinckney rather than Charles Cotesworth Pinckney was the presidential candidate, and that guy is a disaster).

This election isn’t just about the issues, it’s also about fashion choices. You see Federalists are fancy pants Congressman who dress fancy every day and powder their wigs. The Democratic-Republicans are led by TJ, who likes to answer the door in his PJ’s, they are decidedly less fancy. They wear their hair short and “require little personal attention”.

In 1808, the fancy pants Federalists think they have a chance with Pinckney, after all, Madison is no TJ. He’s not as charismatic, and Madison lacks TJ’s political charm and savvy. But TJ also isn’t super popular. That Embargo Act gets less popular by the day. It’s dubbed the “Dambargo”. TJ is less of a hero and more of “an infernal villain”.

The Federalists cry Madison is a Frenchman, pointing to some honorary citizenships Washington, Hamilton, and Madison received. They’re Napoleon supporters, lets get em! It was rough going for Madison. Not only were the Federalists against him, George Clinton, in his own party seemed to be plotting against him too.

Leading the lets get em charge is George Clinton, who said he had papers proving Madison and TJ were on the French side and hell bent on having an anti-British policy, even at the expense of Americans. It turns out those papers proved nothing, and just made Clinton look terrible and untrustworthy. The papers after all, were supposed to be classified. TJ releases letters proving it’s all BS and it is read in Congress in front of an angry Vice President George Clinton. Basically, this is even more reason we eventually move to a president and vice president running together.

17 states will choose their electors in various ways and on December 7 ballots are cast. Madison wins 122 to 47. For the Federalists, they make some gains in the House and Senate, but fail to get a majority in either. Pinckney got 33 more votes than in 1804, but it’s clear the Federalists are in need of some fresh blood.

Three days before James Madison is inaugurated, Thomas Jefferson leaves him with a parting gift. He repeals the Embargo Act. Instead of suspending trade with all of Europe, we’re going to just suspend trade with Britain and France. American merchants find other trade partners, like the Netherlands, and are overall pretty happy.

James Madison, looking more like an undertaker than a politician with his parchment thin skin and black attire, is sworn in as our fourth president, and at Dolley’s suggestion parties the night away at a ball with a crowd of 4,000 (at a price of $4 a ticket)! It may be a few too many people. Windows have to be broken to let air in. James would “rather be home in bed”, but Dolley is in her element. A party goer notes “She was all dignity, grace, and affability”.

Dolley is going to shine in her new role with her warmth and vitality, after all, she’s an experienced political wife by this point. She was the de facto female voice for the Jefferson administration, and she had been schooled in the Jefferson tradition of entertaining. We’re going to make things simple, not aristocratic, where everyone can mingle, laugh, and tell jokes.

She’ll be a valuable asset to James. He trusts her to advise him, though she does say “politics are the business of men, I only care about people.” More than that, she is going to become more famous at the time, and in history, than her husband.

See, 1808 in DC is basically a sausage fest with nothing to do. DC is only 17 years old, so when Dolley throws the first ever happy hour at the White House two months into James presidency, government officials finally have a reason to bring their wives to DC. Not only that, Dolley is going to invite anyone from any political party. It’s the first bipartisan gatherings outside of Congress!

Politics is also a rather violent affair in the early days in the country, with guys often settling political disputes by way of duel. Dolley would invite them all over and they’d all play nice. We can be in the business of politics and be civilized! Or at least civilized enough not to challenge each other to duels every time we disagree. She’s going to smile, shake hands, and have a conversation with anyone and everyone, even Madison’s political foes. In fact, she even gets a couple of Congressman to call off a duel.

Dolley’s Wednesday evening receptions would become legendary. They’re not stuffy, boring affairs. Instead they’re awesome sociable events, where everyone had an open invitation. There’s cards and chatter with gusto and panache. Dolley’s popping champagne sending corks across the room, using snuff (tobacco) and offering it to anyone and everyone. She organized the parties to help Madison’s career, but she never favored one guest over another. She’d even be friendly with the servants.

Nobody ever felt excluded in the Madison white House from servants to VIP guests like famous author Washington Irvin. Word spread and the parties got a sort of celebrity status, even making the cover of a Philly magazine (in the days when women weren’t mentioned let alone featured in articles), but everyone was still welcome. Dolley Madison: engaging with all, offending none.
It probably helps people can’t take their eyes off Dolley. She enjoys wearing the low cut dresses made of silk and satin, distinctive elaborately folded turbans with bright colored feathers up to a foot high, scarves, emeralds and make up. She is a style icon, a fashion diva, the Jackie Kennedy of her day.

It doesn’t hurt she’s serving ice cream either. Sure, she likes oyster flavor ice cream (gross) but she also introduces everyone to “strawberry bomb glace”, a French delicacy, and the official White House dessert. She also serves chocolate and imported treats, and might have invented the “whiskey sour”. Everyone wants to know what Dolley is serving!

James just gets to stand back, let perky outgoing Dolley get all the attention and be his social shield. He’s got bigger things to deal with. The Embargo change made Americans happier, but it didn’t calm the tension between France and Britain, and the Brits are now stealing US ships and cargo. They’re still kidnapping US sailors and forcing them to serve in the British navy, and now they’re giving Native American weapons to attack American Settlers.

James Madison has tried his best to stay out of war. He likes to really think about things though, and he is delaying any decision as long as possible. He looks indecisive. But he’s just trying to be sure. He believes were unprepared for war (and we are, in part because of Madison’s own anti-military polices), but starting with George Washington, presidents have tried to keep the new country out of war, believing the young US was still to fragile to endure a war.

But most of the country are non “War Hawks”, they want war! In the 1810 midterms there was a Revolution in Congress, where a bunch of aging, creaky old men get voted out and are replaced with a new blood. It’s the blue wave of 2018. The Idealistic young guys are War Hawks, who want to make Britain pay for years of insults. You might have heard about some of these new guys clamoring for war, they include John C. Calhoun and Henry Clay (Henry Clay also shows up to Dolley’s parties, and announces “Everybody loves Mrs. Madison”, Dolley replies with “that’s because Mrs. Madison loves everyone!)

Clay and Calhoun want to defend the US at sea, and drive the British out of Canada, and push Spain (Britain’s ally) out of East Florida and add it to the US (though not the way Andrew Jackson wants to do it, remember he’s down there now killing Native Americans and whoever else gets in his way).

Were at 1812, and everyone knows war is in the war. But also in the air? The Election of 1812!
First of all, in April of 1812, Vice President George Clinton dropped dead. So when James gets the re-nom in May, the Democratic Republicans are going to have to find a new Vice Presidential candidate, and they’re going to pick a “Gentleman Democrat”, a signer of the Declaration of Independence, former Governor of Massachusetts, Elbridge Gerry.

Elbridge Gerry is not so important in his role here, except to note that his energetic redistricting to Federalist voting areas in the Democratic-Republicans favor is where we get the term “gerrymandering”. Yes, structuring districts to benefit one party has been going on for over 200 years. Elbridge Gerry won’t really go down in the history books, but Gerrymandering will.

Most of the country wants war now, and it just behooves Madison to go along with it, so one month after getting the nomination, Congress declares war on Great Britain. They believe Madison needs to take a hard stance, to free the US from Britain once and for all.

For Madison, the war is a benefit to running for re-election. He doesn’t have to worry about his campaign, he’s got bigger fish to fry.

Remember how I said the Federalists are going to need new blood? Well, they won’t even nominate a Federalist guy. With the whole country behind the war, they try and support a candidate they think can be all things to all people: DeWitt Clinton.

Wait, any relation to the barely in the ground, dead ex-Vice President George Clinton? Why yes, Veep Clinton was DeWitt’s Uncle, and Uncle George taught him everything he knows! Yes, James Madison is going to run for president against his dead Vice President’s nephew, his favorite nephew at that.

The Clinton’s (no relation to Bill), were a prominate family. Of course Uncle George was Vice President to TJ and Madison,  and DeWitts dad was a Revolutionary War General (James Clinton). DeWitt is something of a boy wonder, a total overachiever. At age 17, he graduates 1st in his class at Columbia, and gives his commencement speech in Latin (show off!)

By 21, DeWitt is Governor Uncle George’s personal secretary. This early experience in politics introduces DeWitt to all the important people, and Uncle George steers plenty of people to DeWitt’s law practice.

A young grad student DeWitt even lived with Uncle George for awhile in NYC (then capital of the United States). DeWitt knows everyone, including a guy who lives at the end of his street: current President George Washington. Washington doesn’t have the White House to live in right now, so he’s renting from this guy Walter Franklin. Franklin has two daughters. One of them, Maria, marries DeWitt, and another one married DeWitt’s brother, George. It’s a small world in late 1700’s politics.

Maria’s family had some money, which means now DeWitt has some money (customary for the time), and the couple have two homes one in the city, and one in Long Island. They have 10 kids and turn the city house into a school house full of test tubes, plants, stones, fossils, and lots of tools and equipment for astronomy and weather experiments.

DeWitt is a science guy. He likes to be forward thinking. He has a love for natural science and philosophy. If politics doesn’t work out, he’ll surely be a professor of natural science. His hobbies include flowers and plants and collecting rare books. He speaks Latin and Dutch. he’s an intellectual giant who thinks big. But he’s also a physical giant, at 6’3” and 220 pounds. He’s a dynamic guy, and a great public speaker. He’s called “Magnus Apollo”.
Back then, mayors were appointed, and governor Uncle George is going to appoint DeWitt mayor of New York City. H’'s going to be to NYC what Ben Franklin was to Philly. As mayor DeWitt is spear heading new initiatives in physical infrastructure with streets, canals and sanitation.

He’s progressive and imaginative, promoting city public planning, public education, public snatiation, and relief for the poor, instituting lots of programs for the less fortunate.

DeWitt is as clean as they come politically. Sure, Uncle George showed him the ropes, but he’s never taken a bribe or given favors. In gact, he won’t even take a dime in port custom fees, something he was entitled to do as mayor. He lives on Maria’s money and his modest government salary.

Besides being mayor, at the young age of 32 he had been a US Senator for New York, where he worked on the 12th Amendment (so we wouldn’t have another Aaron Burr/TJ debacle), and he reduced the waiting period for immigrants to become citizens (from 14 years to 5). He only resigned to be NYC mayor.

DeWitt is a successful politician, a good looking young guy (he’s 43), but he isn’t a particularily outgoing guy. He’s not winning any “good old boy” competitions, but he’ll command respect. People in New York City are much better off because of DeWitt Clinton, and if he’s elected president the whole country will be better off.

Federalists see his potential. One problem? The guy is actually a Democratic Republican. But, the Federalists see an opportunity. If the anti-war and fancy pants New England Federalists combine forces with the Anti-War Democratic Republicans maybe they can beat Madison. They think the perfect compromise candidate is DeWitt.

Now, the compromise candidate is going to be the beginning of the end for the Federalists (Sorry John Adams, and Alexander Hamilton). It’s ironic, because their ideas are now so ingrained in American fabric. We have a national bank, and standing army, and a strong central government to handle unruley states. But as Americans spread out across the country they look for a broader more democratic view of the new country, instead of the rich and powerful who only seem to care about the rich and powerful states across New England. Their opposition to the War of 1812 is also going to cost the Federalists dearly, and then they try to succeed from the union. It’s not a look and the Federalists fall into obscurity.
DeWitt isn’t perfect. He does have some cons. He’s a risk taker. He’s not afraid to speak on controversial topics (let’s abolish slavery!), and he’s kind of a smarty pants (it’s almost sad we never get to see a Madison, DeWitt debate!). He doesn’t have casual friends. He’s forgetful of people and doesn’t remember people’s names. It’s also kind of hard to carry a conversation with him, because he knows so much he often comes across as arrogant. He’s also pretty quick to duel, and once he gets to the duel, there will be no draws. Instead he insists of going round after round until someone gets shot. If he gets elected he’s going to have to show more tolerance.

In 1812, the burden of getting elected didn’t fall to the candidate, it was a party job. The Democratic-Republicans that support Madison have a unified message and a unified front. It’s time to beat the British once and for all.

But the Democratic-Republicans and the Federalists backing DeWitt Clinton are anything but unified. DeWitt almost becomes a different candidate depending on where he’s running.

Sometimes it’s “Madison and War, or Clinton and Peace” if he’s talking to people against the war, primarily appeasing the north and the Federalists.  If we’re talking about the south, where war was more popular, Clinton was presented as a guy  who liked the war, but would do war better than Madison” (Not an exact quote).

In the end, quiet sickly James Madison benefits from the elections of his day, where candidates don’t have to attend rallies of give speeches. DeWitt will win 7 states, and 89 electoral votes. James Madison will win 11 states in the south, and 128 electoral votes. Not now, not ever, will the United states ever vote a president out of office during war time.

But, there is really something interesting, and rarely recognized, about the electoral map of 1812. It’s split as if the country is giving a preview to the Civil War 50 years later. 120 of Madison’s electoral votes came from states south and west of the Delaware River. 80 of Clinton’s came from states north and east.

The reason Madison is elected? Ironically, it’s the southern slaves who “vote” him into office. There is a famous 3/5 clause in the Constitution, designating slaves as counting as 3/5 of a person. The south used the number to bolster their electoral numbers, even though the slaves could not vote. For 58 of the first 70 years of the United States, slave holding states held the presidency thanks to this rule. In fact without out, Thomas Jefferson would not have won in 1800. And DeWitt Clinton would have been president.
DeWitt might have avoided the Civil War too. He wanted to unify the economies of the north and south, who were separated by static farmers vs. northern merchants. The southerners needed those slaves to run their plantation. But, if they didn’t depend on their slaves tending to their plantation, maybe the Civil War wouldn’t have happened. Remember, part of the reason Lincoln issued the Emancipation Proclamation was so the south would lose all the labor on their plantations. But what if that had already happened? What if DeWitts plans to have a unified, non-competitive economy could have averted the Civil War?

Instead DeWitt will go back to New York, where he will eventually be governor. He pushes for the construction of the Erie Canal, which will join the great lakes to the Atlantic Ocean and open up the western states to goods from the east. Madison isn’t a fan and even vetoes the idea. So DeWitt decides New York will do it on their own, and he uses free (not slave) labor to get the greatest public works project since the pyramids built. While we take the Erie Canal for granted now, connecting those two sections of the United States would prove vital to the prosperity of the country. The day it opened, all the living ex-presidents showed up (Jefferson, Adams, Madison, Monroe), and even recently defeated presidential candidate, Andrew Jackson was there.

DeWitt had backed Andrew Jackson in his loss to JQA, but JQA still offered him a job as Minister of England. DeWitt passed. He was hoping Jackson would win in 1828, and Jackson (one of DeWitts buddies) would make his Secretary of State.

But fate intervenes in February of 1828, 57 year old DeWitt Clinton dies. Of course, we know Jackson wins, and his Secretary of State slot will go to Martin Van Buren, who will go on to become Jackson’s veep, and eventually president. That could have been DeWitt if he had just lived long enough. He could have had a second chance to head off the Civil War.

But, DeWitt was dead, and today he barely registers as a blip on the radar of most people. TJ once called him “the greatest American”, Abe Lincoln is asked who he most wants to emulate and he says “DeWitt Clinton”, but today you say his name and everyone asks “Any relation to Bill?” (No).

Enough of the ‘what if’s though’ we have to head back to 1812 and see how the recently re-elected James Madison is doing with that war with the British. The short answer? Not great. We just aren’t that prepared for war, and we suffer some humiliating defeats.

Dolley will publicly support James though, squashing any question that she doesn’t support the war effort (with that Quaker background and all), she even organized relief for war orphans, because she’s Dolley-freakin-Madison.

James gets it together, guards the ports and sent ships out in groups (safety in numbers). He has no combat experience, but nobody’s going to attack the country on his watch. He will become the first and only president to command on the field while president. The anti-war guy who has never fired a gun before, grabs two pistols, and rides out on horseback to fend off the British. Plus he’s got William Henry Harrison battling the British and the Native Americans in the Lake Erie region, what could go wrong?

Well, in the summer of 1814, the British get serious and they want to capture DC and take the country down. Admiral George Cockburn is getting cocky and he’s going to stroll into town, kidnap Dolley and parade her through the streets of Great Britain.

Dolley is Dolley though. She’s not scared. She’s preparing a dinner party when she gets word from Jemmy (as she called James) that she needs to get out of dodge. And Dolley is like, not without a few things first! She directs the staff to load up and send away important papers, and valuable items. She even had them grab the silverware and some red curtains.

But most iconic-ly she directs them to grab the portrait of George Washington, except it’s stuck on the wall. They can’t get it down, so they break the glass, tear the canvas from the frame and send it off to safety.

Dolley even sends her pet parrot “Uncle Willy” to the French consulate to keep him safe. And she does it all while staying cool, calm and collected. She leaves the White House just in time, and when Admiral Cockburn shows up, dinner is still set at the table. So, him and his men sit down, eat the meal, and then promptly burn the White House and Capitol to the ground.

The next day a hurricane (or just a really bad storm, we don’t know, the early 1800s lacked good meteorologists) rolled into town, putting out fires and causing the British to retreat.

But just a few weeks later, the US will hold off British ships in the Battle of Baltimore. Frances Scott Key will write the Star Spangled Banner, and the war will turn once and for all in the favor of the Americans.
Of course Andrew Jackson will become a “hero” in the Battle of New Orleans, and John Quincy Adams will get the British to sign the Treaty of Ghent ending the war, and the Revolution once and for all (though not in that order of course).

Madison is now the hero who beat the British once and for all, and Dolley’s daring act of saving what is the White House’s oldest possession earns her even greater public admiration. The Capitol and the White House needed rebuilt, and Dolley didn’t bat an eye. She dusted herself off, picked herself up, and gets back to the business of throwing parties, even in her temporary residence while the White House got repaired. Oh, and remember those red curtains Dolley took? Well, she had them made into a dress to wear to functions celebrating the American victory over the Brits.

By 1815, the Madison’s are the ‘toast of the town’, and will help usher in the “Era of Good Feelings” and an economic boom that new president James Monroe will enjoy.

James Madison retires to his home in Montpelier with Dolley, and just a short carriage ride away from his buddy Thomas Jefferson, who he helped form the University of Virginia. He spent his final years financially stretched. Montpelier was seeing poor crops of wheat and tobacco and what money they did have was used to pay off the gambling debts of Dolley’s alcoholic son, Payne.

But a little money isn’t going to stop Dolley from here hostess ways. Instead she’d host so many people, tables would often have to be put up outside to accommodate all her guests.

 In retirement “gloomy stiff creature” Madison came alive. He becomes more playful and jokes around. He takes daily horseback rides through his 5,000 acre plantation over looking the Blue Ridge Mountains. Friends visited with him, and they’d sit on the porch, drink coffee and smoke cigars while James told them stories about all the famous people he had known, with a twinkle in his eye. He was said to be “great fun”, was charming and funny and would rattle off a stream of historical facts. If there is one president I could meet toward the end of his life, it might be James Madison. We introverts have to stick together.

By 1831, James was the last living Founding Father, the last living signer of the Constitution, the sole Continental Congress survivor. He died in the summer of 1836 at the age of 85 of heart failure. He was buried at his Montpelier estate.

Dolley has some good years left (remember she’s 17 years younger than James!) so she moves back to DC. Her terrible son Payne continues to leach off her, and Dolley is so poor visitors to her house leave money for her to later find. But, she is still the most beloved figure in DC. The founding fathers may all be gone, but Dolley is a tangible, beloved link to them.

She is awarded a seat in the House of Representatives (which had never been done before for any American woman, and it’s done so by unanimous vote), She gets to send the second message in morse code (after Morse himself!), and she helps President Polk lay the cornerstone of the Washington monument.

She’s so beloved, until she dies at the age of 81 in 1849, she is seen as the “Queen Mother” of the United States, and it’s customary for new presidents to seek her blessing.

Her funeral is a who’s who of American royalty and she is given a send off fit for an Empress. Current president, Zachary Taylor says she is “Our first lady for half a century” and the term sticks.


As far as James presidency goes, historians blame him for bad international diplomacy, after all, DC did burn on his watch. Maybe he wasn’t a great president. But the guy was a great statesman. His writing ability is impressive and legendary, but his presidency, not so much. He doesn’t pass the litmus test of presidential enduring fame. He only made it onto the $5,00 bill, which has long been discontinued.

Really, what he’s remembered for is being Dolley Madison’s husband. And if you think about it, that’s probably the way Jemmy would have wanted it.