It's great to know that even back then, when the criminal needs to flee somewhere, where do you go?
Florida? Florida, you're so incorrigible, has this kind of like mischievous pirate thing going that I kind of like, oh, Florida, you've gone and done it again. Welcome to Snaffu, the podcast about history's greatest screw ups. I am your host ed helms, and each episode I drag a brilliant guest through one of these disasters and we ask ourselves, what the hell does this tell us about us as human beings today? My guest is one of my oldest and
dearest comedy pals. He's a writing legend snl The Office, co created Parks and rec Brooklyn ninety nine, The Good Place Rutherford Falls, And by the way, he directed tons of all those episodes as well, and oh don't let me forget out of all of us who worked on the Office, he was also the best actor. Yeah, he's the one who brought the legendary Mose Shrewd into all
of our hearts and nightmares. Of course, he just got a very well deserved star on the Hollywood Walk of Fame, and at this point, I'm pretty sure NASA might be trying to name a planet after him. Please welcome Mike. Sure, Hello, Mike. What a wonderful introduction.
Thank you, I mean thank you first of all for highlighting my acting, because I think you know that's the legacy that I hope to leave this earth with more than anything else.
I don't think you get enough credit for your acting, and I don't agree you act enough. I think you need to be in more stuff.
I will take any acting job that requires me to a remain mute and be run along the side of a car like a dog.
Let's talk about most for a second, because what went into your choices, the choices that you made as an actor. Was that something that like the writer's room really kind of broke down and was like, it'd be really funny if he was just sort of spooky and almost like a horror movie character just sort of popping up. Or was that just your own brain sort of chewing on it and then showing up to set and being like, I'm gonna get weird.
Certainly, the way that Greg Daniels and the writers wrote, and I'm putting that in quotes wrote the character of Mo's was spooky and weird and just kind of off. My choice is as an actor, I would describe as coming from a white hot panic, just pure panic. Just no one had told me what to do. I didn't know what to do. I'm not an actor, and I
just did anything. I just did anything that I could think of in the moment, and people kept finding it amusing, and so I just kept panicking and doing whatever came to mind.
I love it. I'm glad you enjoyed it. It was a gift to all of America. So thank you the world, really truly. Sure. Yeah, I'm really eager to dig into
this snafoo with you today. But before I do, I just wanted to tell you something because I was thinking about you know, we've known each other for twenty ish years, and we've collaborated very closely in many different ways over the years, and I've talked about you in publicly in interviews a lot over the years, and I realized there's something that I kind of say when your name comes up in interviews frequently, but I don't know that I've ever said it directly to you. And I was like,
I got to tell Mike this. I got to get on the record with Mike Sure, and let you know that the character Andy Bernard on the Office never would
have clicked for me without you. You were such an instrumental part of like helping me find his voice and shaping who he became, and that whole process, all of our fun little huddle ups and just hard laughs and brainstorming sessions about who Andy Bernard could be and why Andy was funny or what made him funny, And it's just like one of my favorite memories of show business. That's so kind of you to say. I mean, I will say that.
You know, you joined the show in season three and the plot was that, you know, Jim had moved to a different office, and the office that would happened to
be chosen was in Stanford, Connecticut. And I grew up in West Hartford, Connecticut, which is maybe an hour and changed north of Stamford, and I just instantly knew and I grew up with Andy a lot of Andy's and it was a very familiar character to me at the sort of preppy, like good time Charlie guy who went to an Ivy League school and just wanted to be liked and was just desperate for like you know, was maybe a little clumsy in the way that he went about it, but had a good soul and a good heart.
And I just remember thinking the combination of that character description and you as an actor. I was like, oh, I know, I get this, I get this. I know exactly who this guy is. And I do have a lot of as I'm sure you do, specific memories of like little moments of like figuring out the exact right little mannerism or sort of prepster little turn of phrase or something that he would give. There was the episode where you all get drunk in the office having to.
Work late at night.
Oh yeah, and start you start singing an Indigo girls Closer to Find, Closer to Fine song, and then Jim chimes in and you pop up a go tuna, like so excited that he also knows all the lyrics to Closer to Find. I mean, that's that was my childhood. That was exactly my child That was like sitting around with my friends and listening to that album in particular.
That's really where I think our friendship forged. Like that's when I met you, was coming onto the office set and just immediately like you were one of one of that handful of people that put me at ease immediately, and I'm so glad. Yeah, I mean, it's just yeah, it's awesome. It was a good time.
It was a very fun, fun time, and I think all of our lives it felt like we were just in a very creative world with a bunch of creative fun people, and our only job was to figure out what was the funniest thing that could have happened at any given moment.
That's exactly our only job was to make each other laugh as hard as possible. Yeah, And I mean, there's no better job, no better job. Well, Mike, I am thrilled your because today's story is basically a political sitcom excellent, only with a lot more graft, more fistfights, and way more dark money changing hands under the table. Today we're talking about Tammany Hall and the legendary Boss Tweed. Fantastic. Yes, how familiar are you with this story? A fairly familiar, I would say.
In the broad strokes, The Powerbroker by Robert Moses is one of my favorite books ever written, and Tammany Hall is a human part of Robert Morris's origin story. And you know, Robert Moses's story is legendary and have covers many chunks. But he his like understanding of politics was forged in Tammany Hall.
All right, well, let's start with some baseline info here, because I think a lot of people have heard of Tammany Hall, but might be one like, what is it exactly? Was it a building? Was it some sort of club or was it a symbol of something opaque and powerful, maybe even a little bit sinister. Well the answer is actually yes, all of the above. Tammany Hall was indeed a series of buildings in New York City, the most famous of which stood at fourteenth Street in Park Avenue South.
But it is in fact so much more than that. When historians say Tammany Hall, they're actually referring to the democratic political machine that controlled New York City politics for well over a century from the early nineteenth century to the mid twentieth century. Tammany Hall was part fraternity, part mafia, part city council. Think the Sopranos only the front business. Instead of being a strip club, it was city.
Hall, right, Yeah, it was the machine that ran New York.
And a political machine, by the way, was actually the term for this type of It was not just a kind of random metaphor that I'm using, it was actually what these operations were called for over one hundred years. Tammany Hall decided who got jobs, who got contracts, and often who won elections in the biggest city in America. So, Mike, sure, how did it all begin? Well, let's rewind a little bit, shall we back all the way to seventeen eighty nine,
the same year George Washington became president. Coincidentally, back then, there were a number of prominent fraternal organizations like the Freemasons or the Society of the Cincinnati, and these groups tended to be a bit crusty and aristocratic, little snooty like country clubs. The Cincinnatians were even accused of trying to set up a kind of American hereditary nobility, which is pretty rich considering we had just fought a massive war with England to get rid of all that crap.
The most the most American thing, right is you you're like, no more sovereigns, And then as soon as the king has gone, you're like, what if we had a king?
Nobility's nice good points. So the modern version of these clubs, I think is like we see around as like Masonic temples, or or the Shriners. The Odd Fellows, which actually started in England around this time or even earlier, was also happening at this time, and I think that largely, or the Rotary club Lions.
Well, it's not just those, it's also you know, when you're talking about like societies that aim to pull levers of power, you're also talking about like in the modern day, there's Bohemian Grove and there's the Davos Conference, and there's as long as there have been societies, there have been people seeking to form organizations that secretly control things. And so you know that some of those clubs are more civic minded, some of them are more you know, charity minded.
But you're social.
Yeah, but there's it is always the case that there have been people in every society, even ones that purport to be purely democratic or republic or whatever you want to call them, that are like, wait, we're rich, and maybe if we quietly meet in a room somewhere, we can divvy up the society and capital in a way that will benefit us and not other people. So it's a it's as tale as old as time.
Yah. Indeed, what's funny is that is that they're just as dumb as everybody else, but all kinds of conspiracy theories get ascribed to them. And I just think if you could probably get into those rooms, you'd be like, what the oh, these idiots, this is the group of people. It's like, yeah.
My favorite thing in the world is when a billionaire does something stupid and the reaction is like, well that he's probably not doing that. He's a billionaire, and no, I promise he's just as dumb as everybody else.
Of course, all right, so enter into this landscape of sort of crusty aristocratic societies. The Society of Saint Tammany founded in New York basically as a deliberate fuck you to all of these aristocratic clubs. So this was to be a patriotic club for the common man. It was named after taminind A Lenna Lenape chief, mythologized as a patron saint of America and liberty. Of course, the Society of Saint Tammany also massively appropriated Native American attire, rituals
and nannings and you're kidding, yes, yeah. They not not a real progressive, woke crew at this time, but they threw large events, parties and parades. They were rowdy, populous, and kind of a bit campy or silly. They had a big sense of humor and uh and also probably quite a bit cringe as well. Yeah, I would imagine. Yeah, yeah, so, uh, guess who shows up real early in this in this zone.
Who's Aaron Burr? Yeah? Yeah, that guy revolutionary war Vet, the third vice president and yes, the guy who murdered lin Manuel Miranda. He's a national treasure in Miranda.
Does someone fact check these podcasts or should we do it in real time?
Because I I I asked the Internet and they said that there's a video of it.
I swear to you you got the AI overviewed it.
Yeah, that Aaron. This is all AI generated, including me. I am fast asleep in my house right now. Okay, so no, he didn't murder Miranda. He murdered Alexander Hamilton. And Burr is the one who really saw early on the political potential of Tammany Hall. He saw it not as just a bunch of rowdy fund dudes, but as a ready made voter base. And he's the one who really steered Tammany Hall straight into politics. Okay, So now jump ahead to the early eighteen hundreds, New York is
being flooded with immigrants, especially from Ireland. Between eighteen twenty and eighteen sixty, more than one point six million Irish arrived in America, and most of them funneled right through New York City, of course, the famous Ellis Island, right by the Statue of Liberty there in New York Harbor.
Tammany as an organization not happy about this. They were deeply xenophobic, as were all lot of Americans at that time, and they really resisted this massive influx of immigrants and sometimes violently, not a real welcoming, not rolling out the red carpet, not exactly. But this will change, Mike, sure, this will This will completely flip because somebody at Tammany
Hall did the math, all right. Irish immigrants meant Irish votes, and votes meant power, and so Tammany did a one to eighty and they did, in fact roll out the welcome matt and by welcome Matt, I mean jobs, food, social services, and even protection from the angry Nativists movement. In return, the Irish delivered loyalty at the ballot box. By the mid eighteen hundreds, they weren't just part of Tammany's political machine, they were basically the engine inside of it.
Real talk, Mike, sure, do you see this as smart politics or just ugly exploitation or just maybe exactly the kind of two faced move that defines American politics in every era.
It's a familiar story. They were smart enough to understand the way the wind was blowing. It's also a classic American thing to have a bunch of immigrants to come over to this country and then within a generation be like I don't like immigrants.
It's like what what what? Yeah, you're doing?
But they were, and this was the source of all of their power was they were smart enough to understand that there were waves crashing on the shores of America and they could either try to fight them or surf them, and they decided to serf them. And so that is the method, by the way, thank you very much. That's the key to all of these movements is I understand them, and whether they survive or disappear is do you get on board with what is inevitable or do you try
to fight it? And getting on board is a much smarter move politically. You mentioned the Sopranos there's the scenes in the Sopranos where it's Thanksgiving and the guys in the in Tony's carewer like handing out turkeys on Thanksgiving.
Yeah, by the way, Tammany Hall, same thing invented it only handing out turkeys.
Yeah, like that one, like having a giant free turkey Thanksgiving meal is like, that's a year's worth of votes that they just bought for for you know at the time, what like seventy five cents worth of foul Yeah, fabulous insight.
Mike, Sure, I love the way your brain works. We're going to cut all that out though, yeah, yeah, Oh, I assume you're cutting all of this out right. This isn't going to air. So we have now set the stage and here comes our headliner. Are you ready, ladies and gentlemen, please welcome the man who, well, not well, he's not going to join us, he's dead. But welcome to our narrative, the man who would come to embody Tammany Hall's power, greed and epic corruption, William Boss Tweed.
Have you heard of Boss? You know you're familiar with Boss Tweed? What is his name? What is his name? Conjure for you.
It conjures an enormous, barrel chested gentleman who strolls through the streets of New York and everyone knows his name and he is legendary, and people whisper and point and wave and he waves back.
And gosh, you're just it sounds like an episode of Cheers. It basically is.
He's basically norm but on the streets of nineteenth century New York.
And also not afraid to just hit you with an axe. Yeah. Yeah, he's a very complicated guy because he was enormous both in stature and in girth, and by all accounts are very gregarious and jovial guy. Yeah, really like the kind of like you know, backslap in good time, Charlie, but also like capable of like horrific violence.
Yeah, combination of people like breaking into huge smiles and waving and him waving back, and also moms grabbing their kids and hustling them inside when he walked down the street.
That's what I picture, all right, So let's get into old old Boss tweet here. Born in eighteen twenty three on Manhattan's Lower East Side, son of a chair maker, he actually apprenticed at the family trade, but he had much more lofty ambitions. His first step in chasing those ambitions was the rough and tumble, politically connected world of New York's volunteer fire companies. Isn't that kind of interesting?
Kind of interesting? Yeah, because back then, fire companies weren't the noble, Dalmatian loving institutions that we think of today. They were basically street gangs with hoses they or buckets like. Crews would literally fistfight over who got to put out a blaze because whoever controlled the fire fires were so common, and whoever could control the fires had significant control over the neighborhood and then of course all of the political
clout that came with that. So think think of politics by way of pro wrestling, but with a lot more water damage. Yeah. Sure, thank god we don't have to rely on for profit emergency services anymore for now. Yeah. I'm not sure where this airing exactly. So as we were, as we mentioned before, Tweed was a very gregarious guy. He first joined Engine Company Number twelve before helping found
Americas Fire Company Number six in eighteen forty eight. This company was nicknamed the Big Six and their symbol a flashy tiger. Tweed rose to foreman of this fire company, a position he parlayed into membership in the Society of Saint Tammany. Again if there these fire companies were very politically connected because they had it was just all power broker between these sort of rough and tumble figures and politicians and the leaders of the various wards throughout New
York City. So from there he bounced around a few different roles. He was an Alderman congressman for a spell, found that very boring. Came right back to New York City from Albany. He was even a lawyer for a minute, but he finally found real power on the New York County Board of Supervisors as deputy street Commissioner. What a street commissioner? That just sounds mobbed up? It really does the street commission.
Well, Dodger's an image of like, this is the guy who knows all the other people in the neighborhood, right, Like it's a guy who's like, we need sixty people to do some task, and he's like, I got it, and he just goes out and knocks on all the doors and gets rounds up the crew and yeah, yeah, it's a very mob very mobbed up sounding job.
Well as Deputy Street commission. Old Tweed controlled city contracts, jobs and construction. And this is where tweeds genius for corruption truly flourished. If you wanted your cousin on the city payroll, you slipped Tweed some cash. If you wanted your construction company to build a new school, you cut Tweet a slice, or maybe you would just get the contract and never even have to build the fucking school. It's like they were just cranking out all the cash.
So you've been in New York for twenty years and three of your cousins come over from from Dundalk, Ireland, and they don't know what to do. And you go to see Boss Tweed or one of his minions, and you say, we need construction jobs, and they go, here's three construction jobs. You give us twenty percent of your salary or whatever, and you take that deal because the.
Alternative is And by the way, you vote for us, and you vote for you show up and you vote for us, and if we tell you to, you go to the ballot box five, six, seven, eight, ten times. Yeah, you change your name ten times. It was common like they like they were just stack in ballots. I want to be clear. So this wasn't something that Tweed brought to New York City government. This was the culture of New York City government at the time. It was just
a profoundly corrupt apparatus across the board. The group of twenty aldermen and then there were twenty assistant aldermen who were who were a sort of like governing body in the city, and they were known as the forty thieves like that. That's how people were barnd to them. And this was well before Tweed even entered the picture. So he just kind of came in and was like, oh, I get how this works, and just kicked it up a huge notch. He basically industrialized political corruption in New
York City. And oh, don't forget New York City. You know, it's nothing like it was today in scale, but it was massive for the time, and the economy of New York City was on par with entire other countries nations. Yeah. Yeah.
When we were researching parks and rec we learned about a group of people in a city in California that shall remain nameless, that they incorporated the town and then this group of people who'd been living there for a long time. Basically were like, we want to control this forever.
And so the way they formed the government was it was like, you know, there was a planning committee and a sewer committee and a construction committee and everything, and they had it had three members, and the way it worked was, you know, you served like a six year term, but at the end of the term, you it was some mechanism by which like you named your own successor to the committee, and so then they just all they would like just all switch committees. So they just like
it was brilliant. Yeah, so they and they they their name was the Dirty thirty. It was thirty thirty people controlled the entirety of this town for decades. Because there were rules about how you could only serve on these such committees. State laws, you could only serve on the committees for a certain amount of time. So they just were like, all right, we'll only serve on the committee for six years and then we'll just switch and hand
it to someone else. And we just they kept rotating and as a result, they just controlled every single aspect of the planning of the community.
I'm very curious, how do you think how do you think Leslie Nope would do in Tammany Hall not well.
Now, she as a person who believed in fairness and equality and meritocratic system of achievement.
Sure, and also I think she's someone who assumes the best intentions and others. Yes, yeah, I mean she was no fool.
She's certainly in over the course of the show, had to deal with a lot of corrupt people and understood that people's motivations.
Were not always pure.
But yeah, it would Tammany Hall would not have been a good environment in which she could flourish to the best of her abilities.
I'll be honest, I also would not flourish. Yeah. I feel like my brain just doesn't work the right way for that. And I don't mean that in like a oh because I'm a good person. I just mean like I don't I can't track those complex webs of manipulation. And it's like it's so overwhelming to me. It's but someone like Tweet like he's really like an evil genius.
He also was. He had that sort of like Bill Clinton level memory, So he did he had like an uncanny knack for people names that gives you power, And that's something I've never had.
No, I've forgotten your name, like three times during during this podcast.
Yeah, yes, yeah.
Likewise, no, those people who have like an internal ledger where they know everyone's face and name and also where they live and what they owe you and what you did for them, and can recall that with instant clarity. That's a that's a real classic power grab skill that people have, all right.
Well, as well as things were going for mister Tweed, he would become truly unstoppable during the Civil War. So in eighteen sixty three, the federal government has imposed a military draft and New York City exploded into riots. This was an incredibly tragic episode. Poor Irish immigrants were furious at the idea of fighting a war that they didn't feel was theirs, while rich people could buy their way
out paying for substitutes. Also, black people were being unfairly scapegoaded as the cause of the war, and so they were being targeted for horrific violence. Mobs burned buildings and attacked the homes of Republican elites. It was violent, racist chaos, but of course Tweed saw opportunity.
Of course, this, obviously, you might remember, was dramatized in Gangs of New York. There's the famous sequence toward the end of the movie there. Yes, of course, the violence of that movie is so hard for me. It's so visceral verities, of course, as he's like a genius of like just making it that feel visceral. A lot of historical inaccuracies in that movie, but that is this chapter
is exactly how that movie culminates. Tammany started offering loans to working class men so that they too could pay for substitutes in the draft. It was on paper compassionate, but it also meant those families now owed Tweed money, gratitude, and loyalty. The riots quieted down, and Tammany's grip tightened even further. This is feeling like House of Cards on steroids. Yeah, do you see brilliant crisis management or just sociopathic opportunism?
Sociopathic opportunism? Yeah, how do we make everyone more indebted to us than they were before?
Yeah? Well, from here, things like Tweed just consolidated everything even more. Courts, legislature, city treasury, voting booths. Everything bent to his will. And this is also when he earned the name boss. He became boss was a term at the time for like the leader of a political machine and he was definitely the boss. And here's where the corruption it just it scaled up so epically. Probably the most famous example is the New York County Courthouse. Do
you know this story? I don't think so. Now, Okay, the New York County Courthouse, which is down on Chambers Street in Manhattan. It was built at this time, and it was originally budgeted at two hundred and fifty thousand dollars, which is a ton of money for the time. By the time Tweed and his cronies were finished, the bill had ballooned to twelve million dollars, which is roughly two hundred million in today's money.
Wow, So what what is that? Forty x the original cost or something? Yeah, forty eight x the original bid price?
Great? How does this happen? How does someone pull this off? Well, it's actually pretty simple. Tweed's friends padded every single contract, carpentry, plastering, furniture, even the brooms for janitors, all built at cartoonishly astronomical rates. One carpenter supposedly got paid three hundred and sixty thousand dollars for a month's work. By the way, that's that's in eighteen sixty money. It's million million dollars a plaster
pulled down half a million. The courthouse became less a civic building and more of a pinata stuffed with taxpayer cash, just repeatedly whacked by Tweed's gang and just grabbing all that cash. And that's just one project. And by the way, they didn't even finish They just this. This courthouse went unfinished for for like decades later. Tweed would actually be tried in this very courthouse, which is ironic, but we'll
get to that. By eighteen seventy one, Tweed and his all of his buddies had skimmed off and estimated two hundred million dollars total, which was more than four billion in today's money.
Man, man, they really knew what they were doing, and didn't they they did?
He? Yeah, so he became the third largest landowner in Manhattan. He owned two yachts. I guess yachting was a thing then too. At what point, Mike, sure, does corruptions stop being shocking and just become like slapstick comedy. I mean, this is like when your carpenter is making more in a month than Apple makes in a quarter. Are we still talking about corruption or is this just like Marx Brothers.
Well, it gets to it gets to the cartoonish level where eventually collapse is inevitable because no one ever, ever, ever says, I have enough. Now, I'm going to stop. I'm going to like take what I have and just enjoy my life. It's never enough for folks in this position, so they just push and push and push and push
until they're finally caught or brought down somehow. This is the story of all of these folks, especially the New York folks who were you know, who had this massive pool of human labor and the ability to kind of consolidate power at a time when when the country was
still young and cities were still young. Every movie is about this too, right, It's like the person who's like amassing, amassing, amassing, and then at some point if they just said, all right, I'm good, I'm going to retire, they could live their life there, and generations of their families could live their
lives in wealth and security forever. They just never do, because it's it's a psychosis that just pushes them to the point where inevitably they push too far and someone comes along and takes them down.
And that's what happened to him. But the other thing to keep in mind is that this isn't just something that's kind of like making a fool out of the City of New York. It's also there are financial repercussions
to this. The money is coming from somewhere, it's coming from the city's coffers, and a lot of the city's money is also, you know, been purchased by international investors who are starting to sniff around, like what is going on, Like the it's starting to have real raise a lot of like real financial issues for the city.
Yeah, they're all it's all essentially Ponzi scheme, right. It all depends on this endless influx of new people and new stuff coming in so that there's more jobs, and then there's more construction and there's more schools and more buildings, and at some point it's not fundamentally different from something like Enron or whatever, where like the people at the top are they're going to get away with it as long as the like confidence in the system sustains itself
and then something comes along. In Enron's case, it was the dot com bubble bursting that suddenly, like when the flow of new investors is cut off. Suddenly someone goes like, well, wait a second, now, where has all this money gone? And then they when people start looking into it, finally, that's when the whole thing collapses like a house of cards.
Tweed was really good at kind of shoring up his support for exactly these reasons. Sure, he knew how to play the game, so a lot of the money that he was getting through corruption, he was also giving to charity, so he would so Tammany Hall would sponsor public services like hospitals and schools, and that, of course won him a lot of fans. He would remain incredibly popular within his ward in New York City well after he toppled,
which we're about to get to. He just had a ton of fans, particularly in the working immigrant communities, who finally felt like someone in power had their backs right. So for a while, Boss Tweed looked untouchable. He had the votes, the jobs, the contracts, the courts, even the legislature. But if history teaches us anything, Mike, sure, it's that when Karma and Hubris square up for a fight, the smart money and Karma. Am I right loud of that one. I'm proud of that good. Yeah, you can have a
nice little little line there. You can use it. Okay, all right. So Tweed's operation finally began to crumble thanks to a very surprising thing, and that is the power of satire. H yeah, wait for it. Okay, this is really interesting. So the New York Times had begun publishing a huge expose on the city's finances and all of
this corruption. We're talking reams of evidence that showed the courthouse scandal and dozens of other padded contracts and what ultimately brought the details of Tweed's abuses of power to light. It would take this extra push to really spread the news of tweeds corruption throughout the city. Enter political cartoonists Thomas Nast. So you probably have an actual image of Boss Tweed in your mind, and almost certainly it is
rooted in the cartoons of Thomas Nast. Nast worked for Harper's Weekly, a magazine with a huge circulation for the time. He drew Tweed as a grotesque vulture feasting on the city of New York. He drew him as a giant bag of money with legs. He drew the Tammany tiger devouring actual democracy. And these doodles as it would turn out were devastating. There we go, there we go.
Yeah, that's what I think of as the bulging stomach, like the vest with the buttons about to pop off because of the bulging money bag stomach.
Yeah, and ironically a Tweed suit. M Now here's what's fascinating about these cartoons. Tweed's reaction was like he was furious about the cartoons, and he said, this is a quote, stop the damn pictures. I don't care much what the papers write about me. My constituents can't read, but they have eyes. And he was exactly right. You know, so many of the working population of New York City were just didn't have access to education and so but these pictures,
they were devastating. They were on the covers of things, they were all it just was, they were everywhere, and everyone could sort of immediately understand, oh, this is boss Tweed, and he is corrupt.
This is not this zain't good. And that's say that a picture was worth a thousand words in this case.
Like nine hundred maybe something north of the one hundred, like a lot of words. Yeah, now it's worth noting Nast himself complicated figure. He was virulently anti irish and anti Catholic. Many of his cartoons dripped with prejudice, but when it came into tweet, he was relentless and it worked. He's Boss Tweed. So what does he do? He tries to bribe The New York Times sure to stop with all of this. One founder of the New York Times was allegedly offered five million dollars to spike the stories.
Adjusted for inflation, that's well over one hundred million dollars just to keep quiet. That's wild and insane amount of money. Like how who I can't just can't even imagine bribes at that level in this. I'm sure it's happening, but yeah, it's just wild. I mean a Katari jet is worth what that's worth, that's like a round hundred million. Yeah,
kind of a bribe. I don't know. But here's the amazing thing that that New York Times publisher refused the money, saying, quote, I don't think the devil will ever be higher for me than that. Wow, that's a line too. So the pressure, all of this pressure kind of a guy coming down on Tammany Hall and right onto Boss Tweed himself, it just became untenable and the machine finally cracked. The city comptroller himself, caught up in the scandal, turned state's witness.
He flipped and he testified against Tweed, who was ultimately indicted on two hundred and four counts of fraud and corruption. And I'm sure that was like just the stuff they could actually, yeah, that was just the stuff they could document. He was convicted, sentenced, and jailed, But old Boss Tweed, he wasn't done scheming. In eighteen seventy five, he escaped custody.
But now this is kind of an interesting thing, Like custody was kind of a loose thing, like they were they were still letting him like go out to dinner with go home for dinner with his family and stuff. This was like they didn't want to be rude. Well yeah, I mean he had been. He had given so many Christmas turkeys. That's so like they were just like, yeah, go have dinner with your family. At one point, just come back. You got to come back, though, you got
to come back. Well, one night he didn't come back, and he disappeared from New York City. He made his way down to Florida and under an assumed name, and then to Cuba and then he got on a ship to Spain.
It's great to know that even back then, when the criminal needs to flee somewhere, where do you go Florida?
You just go to Florida.
It's just been the haven for criminals and misfits for since at least the mid nineteenth century. I like knowing Florida is nothing of not consistent. There's something I don't know. There's something like I have this like.
Like like Florida, you're so encorurrigible, scoundrel. Yeah, you scoundrel has this kind of like like mischievous pirate thing going that I kind of like, it's Florida. You've got it on it again. Avenue. It's like people running giant bags of cocaine and shooting each other. But then in the afternoon they just like have their moheedos, turn on the Jimmy Buffett and.
Just get out a fan boat and down some tequila and hang out in Florida.
Yeah, man, come on, look, listen, we're incorrigible. What do you want Florida Weather's so good? Come on now, all right. So he made it to Spain, and this is really wild because the cartoons still haunted him. According to some accounts, Spanish police recognized him because of Nast's caricatures, and which is also a testament to the scale of this news. It was breaking it what really was international news, and it was setting off alarm bells in financial markets around
the world. But yeah, Spanish police likely recognized him, and they called their American guys and them were like, hey, we're sending them back. So he got sent back to the United States, imprisoned again, ultimately died behind bars in eighteen seventy eight, age fifty five.
I mean, for a guy of his earth in that time period, it's yeah, you know, that's not terrible.
The Tammany tiger had roared its last roar, so even with Tweed gone, Tammany Hall did not vanish overnight. The machine limped along for decades, turning out mayors and deal makers well into the twentieth century. But when FDR was on his road to the presidency in the early nineteen thirties, he campaigned as an anti Tammany New Yorker, and his win was basically the final wrecking ball for Tammany Hall. The clubhouse doors finally shut for good in the mid
twentieth century. Mike sure. That is the story of Tammany Hall and Boss Tweed, the biggest, baddest, most corrupt machine New York City ever built. Do you have any sort of larger, big picture takeaways? For me? I was really struck by the role that media played in this story, and particularly the role of comedy cartoons. Right. It wasn't the cops or Congress or even rival politicians who brought down Boss Tweet. It was journalists and cartoonists.
I'll say a couple of things. Number one is one of the best things about this country, this screwed up, messed up, messy complex country that we live in, is that in the First Amendment, it says very clearly the government cannot put you in jail for or prosecute you in anyway for speaking up and saying what you believe.
And it also says that the media is free. And because of that, we have a system by which newspapers in history, and television shows and radio programs and other media outlets are allowed to point out and make fun of and highlight corruption in government. That has always been true. It is in theory, I would say, still true today. When I worked at Saturday Night Live, which was my
first job. Jim Downey, who's probably the greatest political satirist, He's the Thomas Nast of his day, really wrote the famous debate speeches sketches between Bush and Gore in two thousand and you know, the famous the first debate sketch involved, you know, summarize your campaign in one word in Al Gore Darryl Hammond as al Gore said lock box and Will Ferrell, as George Bush said strategiery. And that line
stuck to George Bush so thoroughly. He did have a lot of malaprops in his day, but there's a large number of people who believe that he really said that, that he really said strategicy. At one point, there's a lot of people who believe that Sarah Palin said I
can see Russia from my house, she did it. Tina Fay said that as Sarah Palin on SNL, and that that tradition that is very much in the Thomas and As tradition, right is there's a difference between the way people understand the world we live in and the country we live in from dry media reports about fraud and corruption everything else and the way that we see it through comedy and comedy is often a more powerful weapon and a more direct way to make people understand something
about government and corruption and fraud and whatever else is going on than actual news. And that's while I was thinking of as you were telling this story, is is thank goodness that this country allows us to do that, because I believe that is the most effective way often for people to come to understand what their political leaders are doing. And that's what Thomas Asked did to Boss Tweed, and that's what Jim Downey and other folks have done to politicians through SNL cold opens over the years.
Do you think that culturally we actually kind of underestimate the power of Joe folks like can Humor still land a knockout punch? I'm thinking about south Park right now. Yeah, is really appears to be puncturing the armor of this administration in a very startling way.
I mean, the media landscape in which we currently live is so much more fractured. You know, at the time, Harper's Weekly was probably the most powerful an important institution in media, and obviously there's you know, there's barely newspapers anymore, and now there's barely kind of TV. There's no monoculture in TV anymore. We're now in this TikTok Instagram snapchat world where things are very, very fractured. Everybody has their own algorithm. So the question to me isn't whether humor
can be as potent a tool anymore. It's whether the delivery mechanisms that we are employing now can actually deliver a piece of satire to the world that way, or whether people are so siloed off that they'll that, you know, people a large majority of the public won't ever see the same thing.
That's my fear. I know exactly what you mean, and I feel that sense of sort of fractured culture that you're speaking to. But I still have this feeling and it may start be transitioning into more of a hope at this point, but a feeling that truly exceptional work, whether it's a South Park episode or you know, a particularly keen clip of stand up like the cream still rises to the top, and it does, it can still like sort of permeate those I.
Would hope so, because I think if the story of Boss Tweet teaches us anything, it's that, you know, that is what is needed in these moments. What's needed is a voice of satire and clarity and perspective that can cut through and present in a single picture or a single comedy sketch or a single joke. What it would take a scholar, you know, hours to properly relay a picture of a greedy person as a vulture devouring democracy.
Is a lot more effective in a single blow, in a single coup than you know, a lengthy article or a six part series in the New York Times or something like that.
That feels like a perfect place to wrap this up. Can you share what you're working on? I'm dying to know what the latest Mike Sure project is.
So Amy Poehler and I are back together again. We're making a new show called Dig that will be on Peacock sometime next year, we don't know when. Very exciting. Amy and I wrote the pilot together and we're working in the writer's room now. And the extra fun thing is that my wife, jj Fhilban is co show running the show with me, so it's amazing we're ever working together, which is very exciting. And then in a couple of weeks we start work on Man on the Inside Season
three in the writer's room. Season two will drop in November. We're getting a head start in season three the show with Ted Danson on Netflix. So I've got a full a full dance card, as they say. But I would not for a second even think about missing the chance to talk to my old pal at Helms on this podcast, which I really love. By the way, it's a truly, truly entertaining and delightful Well, thank you very much.
Wait, can you give us any like a logline or a teaser about this show Dig with Amy which sounds just utterly delightful, So, Eddie.
It's based on a book called Excavations that Amy read and really liked. It's about a group of women who work on an archaeological dig site in Greece. And it's four women ages nineteen, twenty nine, thirty nine, and forty nine, so four women from four slightly different generations, and they work on this dig site in Greece and they slowly, over the course of the show uncover a sort of like little conspiracy and they all left it.
Did some die sours murder each other? Oh, you've seen it, you've read the book. I mean, what else? What are you gonna find? And a dig it's a dinosaur homicide. It just sounds like so much fun and all the people that I love. Yeah, it should be very fun. I'm very excited about it. Great congrats on that, Mike Sure. I'm so grateful for your time and just for the great hang today.
Thank you so might Hang buddy. Thank you for having me and I truly do love this podcast. Thank you for inviting me on right on. I love you, buddy, Love you soon.
Bye. Snafu is a production of iHeart Podcasts and Snaffo Media, a partnership between Film Nation Entertainment and Pacific Electric Picture Company. Our post production studio is Gilded Audio. Our executive producers are me Ed Helms, Mike Falbo, Glenn Basner, Andy Kim Whitney, Donaldson, and Dylan Fagan. This episode was produced by Alyssa Martino, Tory Smith, and Carl Nellis. Additional story editing from Carl Nellis. Our video editor is Jared Smith. Technical direction and engineering
from Nick Dooley. Our creative executive is Brett Harris. Logo and branding by Matt Gosson and the Collected Works. Legal review from Dan Welsh, Meghan Halson and Caroline Johnson. Special thanks to Isaac Dunham, Adam Horn, Lane Klein, and everyone at iHeart Podcasts, but especially Will Pearson, Kerrie Lieberman and Nicki Etoor. While I have you, don't forget to pick up a copy of my book, Snaffoo, The Definitive Guide to History's Greatest screw Ups. It's available now from any
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