smells like tweed spirit
Or, the unhinged and unrelenting grift of noted dirtbag Boss Tweed.
Hi friends!
US midterm elections are creeping closer by the day, which means I get to indulge one of my favorite hobbies: tracking the weird and wacky scandals of people running for local government. And if we’re looking back at the great sweep of US history, few local-government dirtbags are more distinguished than the subject of this fortnight’s newsletter. That’s right, it’s the granddaddy shitheel of the New York State Legislature:
Boss Tweed, AKA Senator Crimes-A-Lot Himself
I heard of Boss Tweed briefly in 10th grade US history, but honestly the only thing I remembered about him was that a bunch of A+ political cartoons were involved somehow. Friends, dirtbags, countrymen, let me tell you: upon further reading, this guy suuuuuuuucks. And he sucks in exactly the way I enjoy: weirdly, brazenly, and without giving a single fuck. So buckle up, and let’s get into it.
William M. Tweed was born in Manhattan in 1823 to a family of Scottish chair-makers. (Which, I learned today, is a real profession.) In his early 20s, he began indulging what would prove to be a lifelong passion for joining secret cabals of rich powerful white men, becoming not only a Freemason but also a member of something called the Independent Order of Odd Fellows.
Reader, if you think I didn’t get sucked down a hell of a rabbit hole learning about the Odd Fellows, you don’t know me at all. I mean, look at this occult symbolic shit:
It’s like if the White Mom Decor section of Home Goods did a bunch of acid. I’m fucking obsessed. What are the bees for.
But this newsletter is not about the Alice in Wonderland Acid-Trip Beehive that is 1840s secret societies. It is about THE INTERNAL POLITICS OF VOLUNTEER FIRE DEPARTMENTS!!!
No really. It is.
AVFDAB
In 1848, Tweed and some friends formed the Americus Fire Company No. 6, one of many volunteer fire departments roving New York City at the time. Now, these are not the “get the lost cat out of the tree” firefighters you might be expecting. These departments were basically rival street gangs who also happened to own 19th-century fire trucks, and who spent just about as much time beating each other up as they did fighting any actual fires.
Tweed quickly rose to prominence as one of the lead axe-swinging, ass-kicking firemen-gangsters on the Lower East Side. In fact, he made enough connections through this work to get himself elected as an alderman in 1851 at age 27. He whipped through a few more elected offices over the next ten years: New York County Board of Supervisors, US House, New York Democratic Chairman, New York State Senate. Yawn, right?
NOT YAWN.
Because Tweed was doing all this as a high-ranking member of the Tammany Society, an organization that was half-political party, half-secret society in the style of the Freemasons. (Told you this guy fucking loved secret societies.) And as a Tammany Hall rep in his various offices, Tweed started using the society’s considerable political clout for his favorite activities: bribery, embezzlement, and other assorted money crimes.
In other words, he was skimming 15% off the top of basically every government contract. By the end of the 1850s, this asshole had grifted his way into literal millions.
Separately, Tweed also set up a law office and started raking in huge legal fees from his clients, despite the little wrinkle of knowing nothing about the law and being exactly 0% qualified as a lawyer. Frankly, I admire this con and intend to try it out myself someday.
This is also when he started having people call him “Boss Tweed, Grand Sachem of Tammany Hall,” which, besides being wild, is a big ol’ anti-Indigenous-racism yikes.
Carpetbags Through the Ages
By the mid-1860s, Tweed’s political influence had gotten so big that the governor, the mayor, the city council, and every single alderman were essentially on his payroll. What’s more, he’d perfected the art of the grift to a science. Most contractors Tweed hired to do work for the city were encouraged to “multiply the amount of each bill by five, or ten, or a hundred,” and then after paying what the work would actually cost, Tweed would divide the extra millions among himself and his friends.
He did this with the help of his personally appointed city comptroller, “Slippery Dick” Connolly, a name I am presenting entirely without comment.
City contractors leaned the fuck in to this opportunity to make a crooked buck: one guy working on the ceiling of the New York City Courthouse charged $2 million in today’s dollars for about 18 hours of work.
The guys working on the contract for the Brooklyn Bridge were even more dramatic, giving Tweed and his ring of alderman cronies $21 million in today’s money to make sure they got the contract, HAND-DELIVERED IN A CARPETBAG under dead of night. As a Chicagoan, I know a thing or two about alderman-led embezzlement rings, but even so, I can’t help but admire the level of dirtbaggery at play here.
At this point, Tweed was rolling in it. At last, he could kick back and enjoy his secret societies and the fruits of his grift ring. Which he did. Like, a lot. An incomplete list of silly and unnecessary things Boss Tweed did with all his illegal corruption money:
Bought one of the first professional baseball teams
Became one of the single biggest property owners in New York City
Wore giant tacky diamonds pinned to the front of his shirts
Scammed his way into owning the Erie Railroad
Bought a whole flock of canaries from a pet store and had them follow him from room to room in all his mansions
None of the sources I consulted for this newsletter would provide me any details at all about the canaries, which is frankly rude of them, because it’s currently all I want to know about. I’m choosing to picture it like this:
Jingle All the Way
Tweed’s reign of corruption wouldn’t last forever, though. In the end, he was brought down by two things: a pissed-off cartoonist and a one-horse open sleigh.
Thomas Nast, cartoonist for Harper’s and the New York Times, had been simmering with anger about Boss Tweed for the better part of a decade, and in the 1870s, he really upped his game. Political cartoons about Tweed’s stranglehold on city government started flooding the papers, and they were—let me just say—iconic. This is the one you may have seen before:
But this one is hands-down my favorite:
They’re all half biting-satirical-critique-of-capitalist-corruption-of-the-democratic-process, half acid-trip-nightmare-fuel. I love them. Seriously considering ordering a print of the “Boss Tweed as a Cowering Vulture on a Lightning-Stricken Mountain Surrounded by the Bones of New York State Government” framed for my living room.
Boss Tweed was pissed as hell about these cartoons, reportedly saying “Stop the damned pictures! My constituents can’t read, but they can’t help seeing the damned pictures!” I’m not going to make any comment about the modern-day relevance of a quote like that. I’m just going to leave this here and then move on:
Anyway, the other thing that undid Boss Tweed: a wintertime horse disaster. In 1871, Assistant Comptroller James Watson got his head smashed in by a runaway sleigh, and before Tweed could appoint a handpicked replacement, an auditor snuck in and got all of Watson’s financial records, revealing the extent of the grift. Discontent brewed, a riot broke out, and eventually, Tweed was arrested later that year for bold and ridiculous financial crimes.
Tweedle-Dee and Tweedle-Done
Tweed was released from jail on a $1 million bail, which given that his crime was “embezzling hundreds and hundreds of millions of dollars” does not, to me, seem to be nearly enough dollars. As luck had it, he got out just in time for the 1871 New York State Senate election.
I will give you one guess who won the 1871 New York State Senate election.
Yes. Of course he did.
Senator-ship didn’t do much for Tweed as far as rehabilitating his image went, especially because he 100% bought the senate seat, which did not help. He was arrested again two years later, though once again he was released on bail because the bail was too damn low. Finally, he actually went to trial, at which point he was sentenced to one year in prison and fined $12,000.
If you are absolutely screaming at your computer right now, I mean, plus ça change, am I right?
After his release from prison, New York State kept bringing civil suits after him, trying to reclaim some of the TWO HUNDRED MILLION DOLLARS of state funds that Boss Tweed embezzled. (Which, with inflation, is about $7 billion dollars today. Bruh.) To escape prosecution, Tweed pulled what I can only describe as a “Catalina de Erauso move” by sneaking onboard a ship and fleeing to Spain in disguise as a common sailor.
Unfortunately for Tweed, folks in Spain quickly recognized him from Thomas Nast’s cartoons. (I can only assume this is because he’d replaced his head with a big sack of money.) He was sent back to the US, finally actually given substantive prison time, and died in Ludlow Street Jail in 1878.
Well, that’s all for this time, folks. Thank you as always for joining me for another fortnightly journey through history’s shittiest corners.
Until next time, be well, and if you are a member of the Odd Fellows please call me and tell me everything,
-Allison
American political history: sigh.