September 1, 2025

EARLY EPISODE: The Great Siege of Gibraltar (feat. Josh Boerman)

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The largest battle of the U.S. War of Independence took place in... Gibraltar? On the southern tip of Spain? The rock that the Brits care about a lot? And there weren't any Americans involved? Josh Boerman, friend of the show and host of The Worst of All Possible Worlds podcast and Ill Conceived podcast, joins us for this strange transatlantic chapter of American history.

Check out TWOAPW here!

Comments (46)

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Ellie W · October 2, 2025

Replying late but I'm going to have to do a re-listen because I just found out one of my ancestors fought for the Brits in this. Also apparently at Bunker Hill too. The revolutionary was has to be one of the rare times it would have been good for the Brits to have come out on top really...

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Ben Yardley · September 14, 2025

Progozhin was murdered over a disagreement with Putin about whether the Wagner Group were privateers

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Jake sedberg · September 12, 2025

We need York automaton merch

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ArdenIvyy · September 7, 2025

Tabouli Couscous is actually a G Gundam character

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anthony · September 7, 2025

Born in saginaw, the thumb must be respected!!

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Kathy Carrette · September 4, 2025

Tom, Meagher was the first Territorial Governor of Montana. I see a magnificent statue of him outside the state capitol in Helena every day on my way to work. Legit badass.

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Mitch Guerrerio · September 3, 2025

My great-grandfather came over from Italy and became a mailman. He also had a hotdog cart that he’d just tie to his Buick (or w/e) with a rope… in the Bronx.. in 1940 or whenever

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Mitch Guerrerio · September 3, 2025

It’s an Iberrico Pig

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Mitch Guerrerio · September 3, 2025

I love the Ser Davos Seaworth reference

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Thomas Baltes · September 3, 2025

I had a classmate in college actually come down with scurvy. It is one of the funniest damn things I have ever encountered as a person.

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3 Toed Jim · September 3, 2025

So I’m one of the cleanest people alive. I can not stand the thought smelling bad, but I only lather and rinse my hair one time most of the time. I have a head full of thick hair, but I’ll only wash it again if I feel like I didn’t get it clean enough. However, one wash is plenty most of the time.

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Matthew Nugent · September 3, 2025

I’m pretty sure the ice cream wars in Scotland were primarily different drug running gangs using them as a front. Also I genuinely forgot that you are meant to rise and repeat. Ps finish the last two sharpe films #neverforget

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Dawn McKenzie · September 3, 2025

I hate to "um actually" this very good podcast but just a quick thing: Thomas Meagher was actually the governor of Montana, not Missouri (Tom may be getting his wires crossed because Meagher drowned in the Missouri River). Actually read the book I'm pretty confident Tom is now a while ago, the one another commentor pointed out called The Immortal Irishman. Pretty good pop-history book even if some of the literary flourishes in it get a little too close to ahistoricity for me.

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Demagogue604 · September 2, 2025

Not only did they reek from the onions, they were farting something fierce.

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Statistically Hunk · September 2, 2025

You know why the wind in Michigan always blows towards the south? Because Ohio sucks

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Edward Bartlett · September 2, 2025

Forgive me but hearing Josh on the podcast made me think of something... The defense of Gibraltar as an adventures in Odyssey episode. Whit marching up and down a line demanding the troops gather around so he can tell some long -winded story about how if they just have faith, Jesus will protect them from the Spanish.

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Edward Bartlett · September 2, 2025

So our daughter has been homeschooled from grade four up to grade 8 and she's decided to go back to school for grade nine. So we use the podcast as part of her history education. So we're sitting with a teacher who's here to assess where she's at education wise and the teacher asks her what she knows about his history l. My daughter looks at me and smirks and then proceeds to tell the teacher that she's just recently learned about Bubos maxing and " some kind of universal theory. I don't remember exactly what it was called". I also thought you'd appreciate to know "bobos maxing" Is now in regular use amongst her and her friends. So much so that I had a parent call a couple weeks ago asking what it meant.

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NowhereMan661 · September 2, 2025

The Worst of Alll Possible Donkeys

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Alive Or Trees · September 2, 2025

Fun fact about this one - The British leadership had a choice to send relief to Gibraltar or relief to Yorktown, and they chose Gibraltar. So often Yorktown is taught as a checkmate move by the French and Continentals and it was almost a much more contested fight.

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sasquatch6197 · September 2, 2025

Eating raw onions makes me think of the former Australian prime minister tony abbot

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Mutual Aid Miniatures · September 2, 2025

I'm internet friends with the dude that headbutted him. Absolute legend.

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Sam Blackman · September 2, 2025

Jesus Christ more of naval combat/the world before like 1950 being WH40k irl. “Lewk, platforms, PLATFORMS… our enemies hide in wooden BAWKSES! THE COWARDS, THE FEEEWLS!! we… we should take away… their wooden BAWKSES” -British battery commanded while ordering some starving private who has scurvy so bad he looks like he’s just been punched in the face by prime Mike Tyson to melt his hands and balls while carrying a multi-thousand degree hot cannon ball in a wheelbarrow of sand. https://youtu.be/cO3MttgvHUY?feature=shared

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Sam Blackman · September 2, 2025

I love fighting rock-based WW1 where one side is just firing wildly into the air like a Soviet soldier trying to signal for a supply drop at night in ww2…

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Ribs · September 1, 2025

I would absolutely buy a (legally distinct) “THE Ohio State Blood Feud” shirt.

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Ben · September 1, 2025

As a recent US immigrant to Canada I can confirm it is in fact not a “cornucopia of hopes and dreams” but I am 10-15% happier here any given day than in the States

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LensWipe · September 1, 2025

Sounds like Tom is reading The Immortal Irishman!

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JM · September 1, 2025

Gibraltar Island Ohio https://en.m.wikipedia.org/wiki/Gibraltar_Island

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William Shackelford · September 1, 2025

Fuck yes Digletmaxxing mentioned again! let’s go baby! I’m visibly hype now

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Peggy O'Connell · September 1, 2025

Hey! I was a designer on Thief! Glad to hear it getting love.

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The Worst of All Possible Worlds · September 1, 2025

josh (this week's guest) here! come listen to episode 200 of our show and you can hear how much i love your work lmao

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Dorothy Heinrichs · September 1, 2025

Wait so the British soldiers were wearing espadrilles???

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Snorks · September 2, 2025

Heels or flats?

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Oliver Del Mastro · September 1, 2025

Modern major general is from pirates of penzance not HMS pinafore

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The Worst of All Possible Worlds · September 1, 2025

i blew it

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Al · September 1, 2025

Sold out!

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Duke of New York · September 1, 2025

Wait, the Spanish did commit ground troops- Bernardo Galvez fought a brutal campaign against the British in in Georgia and Florida

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Kaiju and Chill · September 1, 2025

I'm fighting my own revolutionary war. Had Thai last night and it feels like I have to pass a Gibraltar.

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AnnoyingSpanishGuy · September 1, 2025

Very disappointed monkeys don't come at play in this

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Ursanoire · September 1, 2025

Canadian here, I just remember it being referred to as the 7 Years War always in school

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TankerBen · September 2, 2025

In the french regions we learn it as being "The War of Conquest"

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Matt · September 1, 2025

“You don’t look the gift dumpster in the mouth.” Ah yes, the motto of every scrounger.

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Noblese Oblahaj · September 1, 2025

My Colonial Romance, a cover band where everyone is dressed as an emo Beefeater

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Noblese Oblahaj · September 1, 2025

They kept smuggling food in on a series of small plates

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Thomas Layton · September 1, 2025

Something tells me we're gonna get some great names out of this.

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P.A.L. · September 1, 2025

Always happy to hear Josh on.

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Noblese Oblahaj · September 1, 2025

I can only tell the hosts of The Worst of All Possible Worlds apart when they aren't talking to each other