Nailing History

Nailing History

Introducing "Nailing History," the podcast where two friends attempt to nail down historical facts like they're trying to assemble IKEA furniture without the manual. Join Matt and Jon (or Jon and Matt) as they stumble through the annals of time, armed with Wikipedia, Chat GPT, and a sense of reckless abandon. In each episode, Matt and Jon pick a historical event that tickles their curiosity (and occasionally their funny bone) and dissect it like a frog in biology class—except they're the frogs, and they have no idea what they're doing. From ancient civilizations to modern mishaps, they cover it all with the finesse of a bull in a china shop. But wait, there's more! In between butchering historical names and dates, Matt and Jon take a break to explore the intersection of history and pop culture. Ever wondered if Cleopatra would have been a TikTok sensation? Yeah, neither have they, but that won't stop them from imagining it in excruciating detail. So grab your popcorn and prepare to laugh, cringe, and possibly learn something (though don't hold your breath). With Matt and Jon leading the charge, "Nailing History" is the only podcast where you're guaranteed to leave scratching your head and questioning everything you thought you knew about the past. After all, who needs a PhD when you've got two clueless buddies and a microphone?

Episodes

March 30, 2026 28 mins

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We start with the kind of problem that somehow becomes a full debate: booking flights, planning a long weekend, and deciding whether checking a bag is smart or “low rent.” From airport security rules to the overhead bin hunger games, we talk through the real trade-offs of carry-on travel versus checked luggage, and why airline policies can turn normal people into petty philosophers. We also hit one of the biggest ai...

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An army can survive cold, hunger, and defeat—but only if it learns how to stand. We dive into the messy middle of the American Revolution, where a self-made Prussian “baron” turns drills into discipline, a battlefield prima donna becomes a traitor, and the British learn that holding cities is not the same as holding hearts. From the gray misery of Valley Forge to the furnace of Monmouth, we trace how training, resol...

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A near-collapse on Long Island. A fog that saves an army. A midnight gamble across black water that shocks a continent. We trace the most volatile stretch of the American Revolution—when Washington loses New York, wins at Trenton, and keeps the fragile cause alive long enough for Saratoga to change everything.

We start with the practical mess behind the Declaration’s arrival in Britain before dropping into ...

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What happens when a twelve-hour history epic meets two hosts who love maps, motives, and messy truths? We dove into the first two parts of PBS’s American Revolution and came up with a sharper, more honest read: there’s real value in the battle maps, the troop movements, and the logistics that make Lexington, Concord, and Bunker Hill feel tangible. But there’s also a framing choice that changes everything—less about ...

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We ring in 2026 with fan calls, a messy production catch‑up, and a deep dive into Death by Lightning, using Garfield’s rise and Guiteau’s delusion to unpack the Gilded Age spoils system and a presidency undone by infection as much as a bullet. Chester Arthur’s surprising turn toward reform gives the story its heart.

• 1880 convention deadlock and Garfield’s dark horse nomination
• The spoils system, sta...

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The plan was simple: drive to Charlottesville, see three presidential homes, soak in the views, and come back with a few good stories. What we got was a bracing look at how history is curated, where it gets messy, and how visitor experiences can either illuminate the past or accidentally hide it in plain sight. We start at Monticello, where Jefferson’s clever design choices and meticulous gadgets share space with a ...

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November 11, 2025 29 mins

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The door slammed without warning: our podcast Gmail was disabled, our recording tools broke, and our notes vanished into a limbo we couldn’t even name. We hit record anyway, tracing the chain reaction from a single login error to a full-stack outage and a $24 stopgap just to keep our voices live. What started as a Sunday session turned into a forensic tour of how one platform account can control your publishing, you...

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Ever wondered why a president can send the National Guard into a city that didn’t ask for it? We light the fuse on a late-night, no-bleeps conversation that links today’s deployments to a long trail of precedent—from George Washington’s march during the Whiskey Rebellion to Woodrow Wilson’s 1916 overhauls and the 14th Amendment’s slow centralization of power. It’s not just a rant; it’s a map of how federal authority...

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We announce our ambitious new project covering each state's journey to joining the Union, starting with Delaware and proceeding in order of ratification or annexation. This special series will coincide with America's upcoming 250th anniversary celebration.

• John recaps his experience hosting an office trivia contest where his fashion choice (suit jacket with jeans) became a controversial talking ...

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June 26, 2025 61 mins

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When newlywed John returns from his California nuptials, the podcast takes a refreshingly personal turn as Matt recounts his best man experience and the unexpected drama surrounding the wedding's signature cocktail. The "Simply Peach Juice debacle" becomes a running joke throughout the episode, as the hosts describe their frantic day-before search for this elusive ingredient, only to run out during co...

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Have you ever paid good money for a disappointing experience? In this continuation of our Virginia adventure, we dive into the reality behind the tourism facade of the Historic Triangle – and it's not always pretty.

We pick up where we left off after Sherwood Forest, as our four-man crew embarks on exploring Jamestown, Williamsburg, and Yorktown. What should have been a fascinating journey through Amer...

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When typical bachelor party debauchery gets replaced with historical site tours, you know you're dealing with history nerds of the highest order. What began as an attempt to check off the "Historic Triangle of Virginia" quickly spiraled into a comedy of errors featuring annoyed tour guides, historical mansplaining gone wrong, and the touching of things that should not be touched.

Our journey ...

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History is built on pivotal moments where the outcome could have gone either way—and perhaps no American moment carries more weight than our fight for independence. But what happens when we flip the script and imagine George Washington captured at the Battle of Long Island, the patriots defeated, and the British Empire maintaining control of its American colonies?

In this mind-bending episode, we examine a ...

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Join us on a sartorial rollercoaster as we navigate the hilarities of wedding suit shopping with our friend Emily M, dialing in from her racetrack-adjacent hideaway in the Poconos. As the best man, I recount my misadventures alongside our groom-to-be, John, whose unique fitness regime of daily push-ups didn't quite prepare us for the comedic chaos at the fitting. Emily brings her wit and wisdom on looking weddi...

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January 23, 2025 84 mins

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Ever wondered how a simple Italian-style egg roll could turn a day into a comedy of errors? Join us as we recount our holiday escapades, from the whirlwind of family chaos to the laughter-filled moments at La Scala's Fire in Philadelphia. The trip for an Italian passport turned into a day of surprises, with a humorous "Italianian" T-shirt thrown in by Matt, proving that it's the unexpected twists...

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Ever wondered what Mussolini and Hitler have in common with a good laugh? Join us on a whimsical trip down memory lane as we recount the year-long journey of the Nailing History Podcast. From our hilariously awkward first recording to the notorious internet mishaps that plagued John's connection, we’ve had our fair share of growing pains. Toss in some peculiar historical anecdotes, like the infamous "wee-w...

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December 11, 2024 83 mins

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What happens when global politics, family ties, and the complex world of presidential pardons collide? Join us as we unpack the shocking overthrow of the Assad regime in Syria and the assassination of the UnitedHealthcare CEO, events that have left the world buzzing with mixed reactions. Our journey isn't just about serious headlines—we also share our amusing adventure of getting verified on X (formerly Twitter...

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Ever wondered how the decisions of a century-old presidency still ripple through today's political landscape? Join us for a lighthearted yet insightful exploration as we kick off with a playful exchange about my co-host John's infamous procrastination and his so-called "990 effect." But it's not all laughs, as we dive into the serious impact of Grover Cleveland's presidency on Native Am...

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Ever had a perfectly innocent morning vote turn into a full-blown drama series? Well, grab your popcorn, because Jon's story starts like a Hallmark movie—he breezes into the polling station, votes early, feels powerful, maybe even a little heroic, basking in the glow of democracy. Meanwhile, Matt's day takes a sharp left turn—he finds out his voter registration is as active as a sloth on a lazy Sunday. No ...

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October 31, 2024 63 mins

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Does Christopher Columbus have a secret Spanish Jewish identity? Join us for a thought-provoking discussion as we challenge a long-held belief about Columbus's heritage and delve into the historical context of Sephardic Jews in 1492 Spain. We unpack the cultural and historical significance of Columbus Day, juxtaposing it with Indigenous Peoples' Day and questioning who truly deserves celebration. Along the...

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