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December 29, 2025 58 mins

Disclaimer: These events are told from the viewpoint of this descendant of one of the first American families. One side came over on the Mayflower; the other to colonize for the crown, participate (on both sides) in the Revolutionary War, had Lincoln as an ancestor on one side; slavers on the other, Quakers, quaffers, and a cabal of creatives from TV, movie-making to radio.

Chapter 10: Founding Fathers — Enlightenment Thinkers with Slaves and Syphilis

The American Revolution didn’t just create a nation—it kicked off one of history’s most ambitious rebranding campaigns. Men like Jefferson, Washington, Franklin, Hamilton, Madison—names etched into currency and concrete—crafted a republic from scratch using Enlightenment ideals, French wine, hookers and, where necessary, a flexible definition of hypocrisy.

They talked about liberty, of course. Endlessly. Liberty was the word of the day, the week, the whole century. But the liberty they spoke of was a very exclusive club—strictly gentlemen only. Membership required land, whiteness, and an aversion to paying taxes unless you were the one collecting them.

Let’s begin with Thomas Jefferson, the man who penned “all men are created equal” with one hand while cradling a whip in the other. He owned over 600 enslaved people throughout his life, including Sally Hemings, a woman he legally owned and personally impregnated—several times.

Enlightened? Maybe. Consensual? Less so.

Jefferson was also deeply conflicted about slavery—but in the same way a man is “conflicted” about eating meat while grilling a steak. He wrote pages on the moral rot of bondage... but kept the plantation running because, well, Monticello wasn’t going to weed itself.

George Washington, the general who would not be king, had wooden teeth, which were not actually wood but rather harvested from the teeth of enslaved people. He freed his slaves in his will—after he died—a final gesture of conscience best described as too little, slightly too late.

And then there’s Ben Franklin, the jolly polymath who did everything from inventing bifocals to founding libraries to allegedly contracting syphilis in every available French salon. He started out owning slaves, then had a political epiphany late in life—roughly around the time it became fashionable in Philadelphia to pretend you were an abolitionist. When I was around 13, I met my grandparent’s neighbor (in Englewood Florida), Benjamin Franklin VIII. This later ancestor had the Franklin family Bible which listed in the back Pages the pounds and shillings the original Ben had earned as one of the world’s greatest “Whoremasters”, running his brothel in Philadelphia. It was around that time that I also read this astounding Founding Daddys’ autobiography which was seminal in helping me develop critical thinking skills and lofty opinions.

Alexander Hamilton, Broadway’s tragic antihero, did not own slaves personally—unless you count the human beings his in-laws owned, whom he occasionally rented. A technicality, perhaps, but not exactly the stuff of moral high ground. He opposed slavery, mostly, but also opposed doing anything practical about it.

James Madison, the so-called Father of the Constitution, was five foot four, owned over 100 slaves, and spent his life talking about the delicate balance between liberty and tyranny while sitting comfortably atop the heads of the enslaved.

These men gathered in Philadelphia, drafted documents with florid calligraphy and righteous tone, and created a government “by the people, for the people”—so long as “the people” excluded women, Black people, Native Americans, and anyone without property. They codified freedom with such straight-faced earnestness, you’d almost forget half of them died surrounded by unpaid laborers and unpaid debts.

Yet, despite all this, they built something lasting. That’s the American contradiction: the same men who drew the blueprint for democracy also nailed shut the door on half the population. And we’ve been living in that contradiction ever since—calling it freedom while debating who counts.

We honor the Founding Fathers not because they were perfect—but because they were flawed and audacious.

Enlightenment thinkers with plantation schedules. Syphilitic philosophers who wrote sonnets to freedom and then foreclosed on it.

They were brilliant, brave, and ambitious.

And yet, what they started was real. Fragile. Glorious. Hypocritical as hell (depending on who you are). But real.

So here’s to the Fathers of the Nation:

* Enlightened, but not fully awake.

* Principled, until the mortgage came due.

* And forever inscribed in history—warts, wigs

Mark as Played

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