Most Americans know Alexander Hamilton from the ten-dollar bill or a dazzling Broadway show, but his true story is far more extraordinary and often misunderstood. Here on Our American Stories, we’re diving deep into the incredible life of a Founding Father whose journey from obscurity to the heart of American power is a testament to resilience, intellect, and sheer will. Get ready to explore the real action, the profound dramas, and the enduring impact of a man who literally helped build the United States.

Imagine a penniless orphan from the West Indies who, against all odds, rises to become George Washington’s indispensable right-hand man and a chief architect of our nation’s financial system. We’ll follow Alexander Hamilton through moments of personal tragedy and national upheaval, witnessing his brilliant mind at work and his unwavering commitment to shaping a new republic. Prepare for a captivating narrative that uncovers the hidden chapters of this American icon and reveals why his legacy is more vital than ever in American history.

đŸ“– Read the Episode Transcript
This is Lee Habib, and this is our American Stories, the show where America is the star and the American people. And all of our history segments are brought to us by the great folks at Hillsdale College. There you can go to learn all the things that are good in life and all the things that are beautiful in life. Their online courses are free. They’re terrific. Go to Hillsdale dot edu. Few figures in American history have been more hotly debated or more grossly misunderstood than Alexander Hamilton. Ron Chernow’s New York Times best-selling biography about Hamilton became the inspiration for the Broadway hit musical. Here’s Ron with the story of Founding Father Alexander Hamilton.

I think it’s fair to say that nowadays even well-educated Americans are largely ignorant about the first Treasury Secretary. They know that he appears on the ten-dollar bill, although you may notice with something of a Hollywood makeover on the new currency. Hamilton, I think, was the best-looking of the founders, but the Treasury Department, in its wisdom, has decided that he needed some plastic surgery. You’ll notice that they have widened his face, and they’ve given him this rugged, square droid look, as if he were auditioning for a Hollywood action movie. There was a marvelous piece in U.S. News & World Report reviewing the airbrushed images of the Founders on the latest bills. And when the magazine came to Hamilton, it positively gushed and I quote, “And asked for Hamilton, he now looks like a real hunk.” So took us two centuries to get a hunky founder where we have him. Of course, the other thing that everybody knows about Hamilton, or at least used to know, was that he was gunned down by Vice President Aaron Burr in a duel in Weehawken, New Jersey, two centuries before HBO and Tony Soprano took over the nearby turf. Burr, you probably know, was the only vice president in American history ever indicted for murder in two states. Yes, and he actually presided over a famous impeachment trial in the Senate of a Supreme Court Justice while Heber was simultaneously on the lam from the law in New York and New Jersey. Never a dull moment in the life of Aaron Burr. Hamilton unquestionably led the most dramatic life of any founder. He was an illegitimate boy born on the British island of Nevis, and he had suffered through a series of childhood traumas that would have shattered a lesser figure. His father abandons the family when Alexander is eleven. His mother dies of tropical fever when he’s thirteen. He’s then farmed out to a first cousin, who commits suicide years later. Calamity is a biblical proportions seem to find their way to this young man. Now, in 1772, in other words, about a year before the Boston Tea Party, a monster hurricane lashes Saint Croix, and this self-taught prodigy sits down and he pens a description of the hurricane of such precocious force and eloquence that the local merchants, recognizing this wonder in their midst, band together to finance his education in North America. The Wunderkind studied at King’s College in Lower Manhattan, later renamed Columbia, King’s being a slightly awkward and inconvenient name after the Revolution. And already as undergraduate extraordinaire, Hamilton is publishing stirring pamphlets against the British. He takes up a musket, and he drills with his fellow students in nearby Saint Paul’s Churchyard today adjacent to Ground Zero, and he delivers spellbinding speeches to large crowds on what is today New York City Hall Park. But this young man, and through all his palpable ardor, is an ambivalent revolutionary. When a rampaging mob of patriots swoops down on the college, hoping to tar and feather the Tory President Myles Cooper, young Hamilton, who was only about five feet six and rather slight of build, courageously stands in the doorway and blocks their path. The young man craves liberty, yes, but he also dreads disorder, and this is a fine balancing act of recurring tension that will characterize his entire career. Before he has a chance to graduate, this slim, blue-eyed West Indian is appointed an artillery captain for the Continental Army. He slips across the fog-bound East River during Washington’s famous nocturnal retreat after the Battle of Brooklyn. He then rises from his sickbed to cross the icy Delaware to surprise the drowsing Hessians at Trenton. And then just a few months later, Hamilton is just twenty-two. That guy who had been a penniless orphan just five years before in the trading house on Saint Croix is miraculously appointed aide-de-camp to George Washington. In fact, he proved so adept at handling Washington’s correspondence, Washington was able to give him the gist of a message and out pops a beautifully worded, delicately nuanced letter from Hamilton that it almost seems like an inspired act of ventriloquism. You will see in this story that, with almost comical Zelig-like consistency, Hamilton has an act for being where the action is. He is always there when history is unfolding. It’s like he’s parachuted into every major event over a thirty-year period. For instance, Hamilton was there at Benedict Arnold’s house the morning that the treason plot was discovered and Arnold fled down the Hudson River. Hamilton found himself consoling the voluptuous but destroyed Peggy Arnold, who lay in an upstairs bed. She was weeping in this very gauzy and provocative lingerie as she faked a mad scene to disguise the fact that she was in cahoots with her husband. Hamilton, I think, was the brainiest of all the founders, but I think it’s fair to say that around beautiful women he shed approximately 50 points on his IQ and he was suckered in by this masterful performance by Peggy Arnold. Now, surprisingly enough, you would think that after this ghastly Dickensian childhood that Hamilton, aide-de-camp and effectively Chief of Stafford George Washington, would be thrilled at his sudden station in life. But he was Hamilton. No, he was chafing at his desk. He dreamed of battlefield glory, and like so many intellectuals then Andre Now, Hamilton was a daredevil who actually enjoyed courting physical danger. At the Battle of Monmouth, he was horrified to find General Charles Lee in full-blown retreat with his panic-stricken men. The young colonel rides up to General Lee and says, “I will stay here with you, my dear General, and die with you us die rather than retreat.” And you’re listening to Ron Chernow, who wrote the book about Alexander Hamilton and inspired the musical, but also inspired readers to know so much more about their founders. And my goodness, what a story he’s telling here to folks at the Library of Congress. When we come back, more of the remarkable story of Alexander Hamilton here on our American Stories. This is Lee Habib, host of our American Stories. Every day we set out to tell the stories of Americans past and present, from small towns to big cities, and from all walks of life doing extraordinary things. But we truly can’t do this show without you. Our shows are free to listen to, but they’re not free to make. If you love what you hear, go to our American Stories dot com and make a donation to keep the stories coming. That’s our American Stories dot com. And we continue with our American Stories, and with Ron Chernow telling the story of Alexander Hamilton. Let’s pick up where we last left off. Hamilton, of course, has his supreme moment of heroism at Yorktown. Hamilton, after mercilessly badgering Washington, is given the command of the First Infantry Battalion to storm the outer ramparts. Picture the scene. Hamilton rises up out of the trench. He sprints across a rutted wasteland, leading his men with frenzied war whoops. Once at the parapet, Hamilton, whom I said was relatively short, has one of his subordinates, Neil Hamilton, step on his shoulder. He springs up on the parapet, and then he exhorts his men to follow. You could almost picture Tom Cruise in the starring scene. Now, despite crushing daytime duties for George Washington, Hamilton, against all odds, manages to give himself a crash course during the Revolution in finance, history, and politics. From camp to camp, this young autodidact is lugging two enormous folio-size volumes called ‘Malachy Postle Fights Dictionary of Trade and Commerce.’ Not exactly light bedtime fare after a day of heavy-duty correspondence for George Washington. Hamilton also totes along six volumes of Bluetarch’s Lives, and he takes the empty pages of a military paybook, and we see him recording notes on foreign exchange, population growth, geography, even European rivers that he will never set eyes on. In fact, in his notes, very interesting notes called from Bluetarch. We see a young man who seems absolutely bewitched by the bizarre sexual practices of ancient Rome. For instance, Hamilton noted that an ancient Rome, young married women seem to enjoy being whipped by lusty young noblemen. Why? Because they thought that it aided conception. I can tell you, when you study our Founding Fathers, you are led down all sorts of unexpected byways. In fact, Hamilton had such a roving eye for the young women that Martha Washington during the Revolution nicknamed her lascivious Tomcat Hamilton, which must have made for some interesting moments at headquarters with George brumbling Hamilton and Martha calling for Hamilton. Now, Hamilton, as you will know, is a very proud, ambitious outsider without money. He lacked what the eighteenth century referred to his birth or breeding. He knew that he needed to marry into respectable family, and indeed, soon after Elizabeth Schuyler, the daughter of a very powerful New York dynasty, visits the Continental Army in 1780, one of Hamilton’s colleagues reports, “Hamilton is a gone man.” The wedding at the Schuyler Mansion is a very bittersweet affair because Eliza Hamilton has this huge, rich family. It’s teeming with all sorts of Van Cortlandts and Van Rensselaers cousins. Well, Hamilton has only a single friend from Washington’s staff, and of course he doesn’t have a single family member in attendance. I mean, think of the underlying poignancy of that emotional imbalance in that affair. And yet the very, very status-conscious Schuyler family always embraces Hamilton as an adored member of the family. Amazing. When Hamilton then launches his postwar legal career, being Hamilton, his exploits again seemed to verge on the superhuman. At the time, he usually served a three-year apprenticeship period to qualify for the law. Hamilton, being Hamilton, manages to qualify after six months of self-study. In fact, he cobbles together a cribsheet of New York legal procedures and practices. He does it so expertly that it becomes a textbook for a generation of New York lawyers. Wonder Boy! He then immediately does something quite fearless and, of course, quite controversial. Hamilton begins to defend the to who had remained in occupied New York during the British wartime occupation, and those Tory merchants were now being persecuted by returning patriots. Hamilton always feared a frenzy of revolutionary retribution. I fear, in fact, it was realized in the French Revolution. He also wanted to retain the capital and connections and know-how of those Tory merchants in order to rebuild New York. Our city lost somewhere between a quarter and a half of all of its buildings during the Revolution. Now you’ll hear it said, and very often it’s taught this way in school, that Hamilton was a ferocious snob, that he was the stooge of the plutocrats of his day. In fact, it would be desperate with Napoleonic ambitions. And of course, in this particular morality play of early American history, Thomas Jefferson is always represented as the pure and virtuous tribune of the people. The situation was far more complicated than that historical cartoon. Case in point. During the war, it is Hamilton, of course, who champions an audacious plan to emancipate any slave who’s willing to pick up a musket for the Continental Cause. In the 1780s, it is Hamilton who cofounds the first abolitionist society in New York, the New York Manumission Society. Remember that trading firm in Saint Croix that I had mentioned that Hamilton worked for as a teenager. That firm had imported up to 300 slaves per year from Western Africa, and it’s clear from subsequent actions that this firsthand experience of slavery left Hamilton with a permanent detestation of the system. In fact, Caribbean slavery was the most brutal in the world. Even those who managed to survive the Middle Passage, their life expectancy once they started working in the sugar cane breaks of the West Indies was somewhere between 3 and 5 years. So you constantly have these poor people who are perishing in the fields, and this supply had to be constantly replenished. Hamilton, despite the historic stereotype, turns out to have been the most consistent abolitionist among the founders. Barnun. I repeat, barn Nunn. Hamilton, it also turns out, had very enlightened views about Native Americans. There is a college in Upstate New York called Hamilton College. Well, the origins of that school had started out as a secondary school that was supposed to educate Native Americans. Hamilton lent his name and his prestige to that undertaking. Hamilton turns out to have had very benign and enlightened views about Jews. He said in an unpublished paper that the success of the Jews could only be explained by Special Providence. So here’s this man whom we’re taught to regard as this ferocious snob, who again and again shows himself as not only devoid of prejudice, but with a special sympathy for the oppressed. Now, I think, with the clear exception of George Washington, nobody did more than Alexander Hamilton to well the 13 squabbling states into the powerful nation we know today. Hamilton personally drafts the first appeal for the Constitutional Convention. He attends; he is the sole New York delegate to sign it. As Hamilton who dreams up and then supervises the most influential defense of the document ever written, the Federalist Papers. Of those 85 essays, Hamilton manages to draft an astonishing 51. No less astonishing, there are periods where he’s publishing them at a rate of as many as 5 or 6 per week. No less astonishing. He’s doing it as a sideline. He had a full-time legal practice. In fact, we have anecdotal evidence of the printer sitting in the outer office as Hamilton scribbles the final lines of an essay. No single treatise on the U.S. Constitution has been cited more frequently by the Supreme Court than the Federalist Papers, nearly 300 times over the past two centuries. And if you chart the frequency of citation, the frequency of citation actually is rising with time, not decreasing. Hamilton, Boy Wonder. The new federal government is created. He hits the ground running. Hamilton is only thirty-four years old when Washington appoints him the first Treasury Secretary. This instantly makes him not only the most powerful person in America, guarantees that he’ll be the most controversial. Why? Remember Washington’s cabinet—and the term was not used. It was originally called the General Council, of just three people. There was Thomas Jefferson, Secretary of State; Henry Knox, Secretary of War; and Hamilton, a treasury. I think fair to say, pound for pound, the best cabinet in American history. Even the Attorney General Edmund Randolph is a part-time legal advisor to the President, lacking that small thing called the Justice Department at that point. And you’ve been listening to Ron Chernow, author of the definitive biography An Alexander Hamilton, called ‘Alexander Hamilton.’ And what a story we’re listening to. He didn’t have the birth, that is, he wasn’t born to bluebloods, obviously. He was born, well, in Saint Croix with nothing, but he had that talent, that writing talent to start. Remarkably, Hamilton drafts 51 of the Federalist Papers, and he did it in his spare time. He was a lawyer and self-taught and just a prodigy. What’s so fascinating about the Federalist Papers that it’s the most cited document in Supreme Court jurisprudence and in case law than any other document there is, and it continues to be cited with increasing frequency. In other words, the writing of Hamilton more relevant than ever in our nation’s battles that are often settled in the courts. When we come back, more of the story of Alexander Hamilton here on our American Stories. And we continue with our American Stories and with the story of Alexander Hamilton as told by his definitive biographer, Ron Chernow. This talk again came from the Library of Congress. Now, in the early days, Jefferson at State starts with 6 employees. Henry Knox st