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On October 27th, 1871, William Tweed began the morning as he did every day, with a cup of coffee and the newspaper. There, below the masthead, was yet another headline excoriating him as a thief, a fat cat, and a robber baron. All he could do was shake his head and take another sip of coffee. But as he raised the cup to his lips,
He heard a knock at his townhouse door and a gruff voice call out, Police! Tweed had always known this day would come. His arrest was years in the making. Estimates vary on just how much money he embezzled from New York taxpayers. Some put the figure at around $25 million. Others say up to $200 million. And now, justice was finally about to be served.
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Today, we're covering the life and crimes of notorious operator William Boss Tweed, the head of the infamous political machine Tammany Hall. In this episode, we're exploring one of the largest and most effective corruption rackets to ever exist. Next week, we'll look at how this power may have been leveraged to make a New York State Supreme Court justice disappear. Stay with us.
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Boss Tweed is a name synonymous with political corruption and scandal. At the height of his power, he was the head of Tammany Hall, the democratic political machine that controlled New York City, and he leveraged that power and influence to become one of the richest men in the country.
His portfolio of ill-gotten assets included stakes in mining, railroad and gas companies, all of which were awarded valuable contracts by Tweed himself. He was the third largest landowner in Manhattan and a director of not one but two national banks.
Tweed grew obscenely rich as the city and its taxpayers suffered, which was an ironic turn. Before he was the king of New York City, he grew up in a working-class family in Lower Manhattan. William Tweed didn't experience a particularly charmed childhood. In 1834, at the age of 11, he left school to apprentice under his father, a chairmaker,
But it was in the streets where he learned to wheel and deal. Tweed was raised in the Five Points District, one of the deadliest neighborhoods in New York City. It was a violent, poverty-stricken area teeming with gangs.
Tweed himself was associated with the Bowery Boys, anti-immigrant, anti-Catholic, and anti-Irish young men roving the streets in stovepipe hats and silk vests. Ironically, Tweed would rely heavily on Irish and immigrant support during his later career, but it was from the nativist Bowery Boys that Tweed got his street smarts.
He would sit on stoops with his buddies all night until the sun rose, guarding their territory. Brawls with rival gangs were common and often devolved into riots. Their main hub was the neighborhood firehouse, since, like many of the other local gangs, the Bowery boys were firemen. It was one way to stake territory and to make a little clean cash.
At the time, when there was a fire, whichever firehouse's team got there first would collect the payment from the city. What happened naturally was that the warring gangs would brawl on the streets, fighting for the privilege of putting out the blaze. It wasn't the most effective system. Sometimes by the end of the fight, the building would be nothing but a smoking pile of debris.
But it was in this chaotic environment that Tweed first distinguished himself. Even as a teenager, Tweed was large and imposing, and he was often the first man off the horse-drawn fire engine. He'd usually carry an axe with him, unafraid of using the blunt end to knock a rival gang member to the ground. By the time he was in his mid-twenties, Tweed was a respected leader in his local fire department.
He was violent and ruthless, sure, but he was also charming with a larger-than-life personality and a loud laugh. And most importantly, he told people what to do. It was no surprise then that when Tweed's first volunteer fire department disbanded, he became the foreman of a new gang called the Big Six and chose the image of a roaring tiger as its symbol.
Then, he caught the eye of the local Democrats. At the time, the Democratic Party bore little resemblance to what we know today. Throughout the early 19th century, Democrats were in favor of slavery and a small government, while Republicans, the anti-slavery party, were in favor of increasing government oversight.
And if anyone was against government oversight, it was Boss Tweed. Democratic leaders began inviting him to dinners, even drinks, and late night chats at men's clubs. They were so impressed by this young man that in 1851, they encouraged him to run for the board of Aldermen, the predecessor to New York City Council. He won, though only after using a little vote buying and intimidation.
Even before Tweed's rise to power, New York City politics were exceedingly corrupt. The malfeasance only increased once Tweed had a seat at the table. He and his aldermen were soon referred to as the "Forty Thieves."
Their brand of corruption at this point was low stakes and consisted mainly of extortion. For example, they might tell a business owner, usually an immigrant, that they couldn't open their doors until they paid a new business fee. A fee that didn't actually exist, and one they pocketed for themselves.
During Tweed's era, an alderman was an unpaid position. So from their point of view, the money they collected from these scams was simply their salary. Tweed's first lucrative scam as alderman occurred when he was put in charge of purchasing fireworks for a citywide party. The fireworks show was so grand and impressive that when he put in the final bill, no one questioned the $4,100 price tag.
The actual cost of the display was $500. In today's money, he fraudulently charged New York City over $160,000. Using a city fireworks show as an opportunity for graft is shameless, but it gets worse. Not even school teachers were immune from extortion. As a self-appointed member of the New York City School Board,
Tweed forced teachers to pay a fee to register for a position, which of course went directly into his own pocket. Then, as now, teachers were not well compensated, and the fee amounted to about a third of their salary. Tweed usually collected those fees in person. At 300 pounds and with a reputation for violence, he wasn't the kind of guy you wanted to cross.
So even if someone suspected they were being cheated, there wasn't much they were willing to do about it. Despite Tweed's hardline ways, or more likely because of them, he was elected to the U.S. House of Representatives as a Democrat in 1853. He spent an undistinguished two years in Washington, where it became clear that he wasn't a backbench pencil-pushing bureaucrat like many of his fellow congressmen.
He was a shot caller. When he returned to New York, Tweed became an official member of Tammany Hall. The Tammany Hall building, located in the Union Square neighborhood of Manhattan, was the headquarters of the Society of St. Tammany,
It was founded as a social club in 1789, but by the time Tweed arrived, it was the democratic powerhouse of the city. It had gained the status by catering to the freshly arrived immigrants flooding the neighborhood. For these immigrants, Tammany was the only organization that stood up for them in a city that was generally hostile to newcomers.
Many had no idea how to navigate New York City, how to find jobs, and some couldn't speak English or even read. The immigrants were lent a sympathetic ear by the Tammany Democrats, but that sympathy came at a price. Before they lifted a finger to help, the politicians required a commitment that the new immigrants would vote for them.
For the immigrants, it was a no-brainer. In their native countries, few had ever been helped by any elected official, much less been given the opportunity to vote. By collecting votes for their chosen political candidates, the organization built an almost unbreakable network of elected officials throughout all levels of New York government. Tammany Hall functioned almost like a union.
Members of the organization had to be nominated, pay dues, and prove that they had sway with certain voting blocs, notably, of course, immigrants. In return, the leaders of Tammany Hall fought for their politicians and won.
The machine became unstoppable. Almost every Democrat candidate in New York politics came out of Tammany Hall, and for over a century, their nominees never lost. That was no coincidence. Tammany Hall's power went beyond the voting booths. They had endless political influence. They granted favors, and they had a lot of money.
Soon it was less of a union and more like a mafia. And just like a mafia, it wasn't afraid of using violence. On July 13th, 1863, rioting broke out in the streets of downtown Manhattan. It came in response to the Enrollment Act, an order signed by President Lincoln initiating a military draft.
The act also allowed for draftees to pay a commutation fee of $300, almost $7,500 today, to avoid military service, an amount no one but the wealthy could afford. Not only did many white working-class New Yorkers oppose joining the Union Army at the height of the Civil War,
They feared that in their absence, their job would be taken by black Americans who, because they were not considered citizens, were exempt from the draft. This frustration led to angry mobs, especially the Irish gangs, roaming the streets and attacking any black people they could find. They burned and looted buildings, including the local draft office and the Colored Orphan Asylum.
Several pro-war newspaper offices were destroyed. Throughout the chaos, the Tammany Democrats fanned the flames by riling up their base and railing against the draft order. It's unknown if they encouraged the violence, but they don't seem to have done anything to prevent it. Finally, after four days, the riot subsided. In the aftermath, 120 people were found dead. Throughout the ordeal,
Tammany Hall backed its members, even offering to pay their commutation fees. As a result, allegiance to the organization grew stronger, attracting the loyalty of German immigrants. Also growing stronger was William Tweed's power and influence. By the time the riots broke out, he'd worked his way up to the very top of Tammany's ladder, and he had a plan to expand their reach.
even further. Throughout the 1850s and early 60s, William Tweed shot to the top of the Tammany Hall political machine. By 1863, the 40-year-old Tweed was firmly in charge. He was given the title of Grand Sachem, the head of the organization. This, not surprisingly, is how he earned his nickname, Boss Tweed.
In his new role, Tweed controlled Tammany Hall's nominations for all city positions. He had to approve each and every candidate. And once he had someone in mind, their victory was a lock. Tweed once quipped, I don't care who does the electing, as long as I do the nominating. Tweed knew that he could count on the loyal immigrant and working class New Yorkers to
and he proceeded to fill the city government with friends who would do his bidding. While Tweed certainly exploited his immigrant base, he also rewarded them. He provided jobs and oversaw the construction of shelters, soup kitchens, orphanages, and hospitals. While a great deal of taxpayer money went into his pocket, much of it also went to Catholic schools and charities. Nevertheless,
Tweed was more concerned with growing rich than children getting a good education. Tweed could also count on loyalty from his inner circle. In return for this, his friends were appointed as the district attorney, the comptroller, the city recorder, packing the city government with friendly faces.
Sometimes he would simply make up jobs when he wanted to put someone in power. And of course, they were all exactly as ethical as the boss. As Grand Sachem, Boss Tweed created a small executive committee within Tammany Hall nicknamed the Tweed Ring.
The Tweed Ring was New York's all-star team of corruption. They overcharged businesses, they billed for services not rendered, they bribed voters, businessmen, and politicians. They actively undermined the economic progress of the city by siphoning off all its money. And all the while, they treated themselves to some very expensive lunches.
At this point, Tweed began to simply buy entire businesses, which he would hire to do work for the city and award with lucrative contracts. Tweed purchased the New York City Printing Company, which naturally became the city's printer for everything from flyers to billboards. He bought the Manufacturing Stationers Company, an outfit that provided all the paper for the printing company, at a significant markup, of course.
and all of it fueled by taxpayer money. The Tweed machine also controlled construction of parks, streets, bridges, hospitals. Architects knew that if they wanted the job, they had to pay Tammany Hall for the contract. In fact, Tweed's most spectacular and audacious act of corruption was the construction of the Tweed Courthouse.
Because of the influx of new citizens, New York needed more municipal buildings. And since Tweed had a seat on virtually every city board, construction of a new courthouse became his pet project. It broke ground in 1861, but would take nearly 10 years to be completed. And during that time, Tweed found every way he could to line his pockets with city funds.
The contracts Tweed awarded and skimmed from were almost comical. Originally, $250,000 was earmarked for the building, worth more than $8.8 million today. By the time construction was completed, the cost was 56 times that.
A single carpenter earned over $360,000 for one month's labor in a building that contained very little woodwork. The plasterer, who happened to be a Tammany Hall functionary, received a staggering $133,000 for two days work. A furniture maker received nearly $180,000 for three tables and 40 chairs.
I wonder how much Tweed's chairmaker father would have charged. If this wasn't flagrant enough, Tweed was also part owner of the quarry that provided the marble for the courthouse. By the end, it's estimated that the Tweed ring embezzled a total of $14 million during the project, equal to a staggering $358 million today.
And as his empire grew, so did his wardrobe. He wore bespoke suits and always accessorized with his trademark, a 10.5 carat diamond stick pin on his shirt front. Not everyone was awed by his sartorial choices though. Tweed's clothing was mercilessly satirized in the press. So were some of his other habits. While he wasn't a drinker or smoker,
Tweed was an indulgent eater who spent lavishly on heaping portions of oysters and duck a l'orange. As a result, the Tweed ring was jokingly referred to as the lunch club. But despite the criticism from the press, by the time of the election of 1868, Tweed had more power and influence than ever. The election is what really propelled Tweed to new levels of infamy.
And he did it through an old, trusted tactic. Voter fraud. The Tammany Hall politicians didn't care if the immigrants voting for them were documented or not. In fact, they made an active effort to recruit undocumented immigrants. To do so, they simply recorded their names, then printed hundreds of fake citizenship cards, on tweed paper, of course, to ensure their participation.
But most importantly, they paid them to go out and vote. On election day, well-heeled young men from Tammany Hall strolled through the immigrant neighborhoods wearing new suits and carrying pocketfuls of money. As soon as they confirmed a loyal immigrant voted for their candidate, the wad of cash got a little lighter. It was a practice they called "walking around money."
Tammany also hired assistant policemen. To all outward appearances, these men, unqualified for the uniforms they were wearing, were on duty to prevent electoral fraud. Aside from that which was sanctioned by Tammany Hall, anyone who questioned the men from Tammany Hall were unlikely to get a straight answer. Anyone who interfered was arrested and barred from voting.
Even the sheriff, James O'Brien, received a generous kickback for looking the other way. But many refused to look the other way, especially the local press. Newspapers referred to the election results as a "nice little arrangement for Tammany Hall."
All of Tammany's nominees won in New York, except for their presidential candidate, Horatio Seymour, who lost to Republican Ulysses S. Grant. The 1868 election was just one part of a larger plan. It all culminated in a document called the Tweed Charter, which would give control of the city's finances, among other things, to the Tweed Ring.
Eleven years earlier, the state of New York had ratified a charter that put the city finances in the hands of metropolitan boards, which were much like the board of a corporation. The more metropolitan board members, the harder it was for Tweed to bribe them all. When the Tweed Charter passed in 1870, it disbanded the boards and gave full control of the city's purse to the Tweed Ring.
They were the only people who could access the treasury. To create the illusion of oversight and transparency, the Tweed Charter also stated that any expense in the city had to be approved by a board of audit, which was, you guessed it, the Tweed Ring. I bet you could also guess that the charter passed through the legislature as the result of bribery?
The Tweed Ring had no supervision from anyone else in the city. They were able to embezzle as much as they wanted without fear of retribution. Not that they seemed particularly worried before. The resulting graft and fraud robbed the city of millions of dollars. Certainly the equivalent of billions today. Tweed's most loyal supporters fell into two basic camps.
working-class immigrants who were swayed by his all-for-show charity donations, and the politicians who benefited from his rule. However, stress in the political machine was beginning to show. The city's economy was failing, crime rates were up, properties were in disrepair, public spaces were run down,
And the only places the city was developing were properties in which the Tweed Ring had a financial stake. The Tweed Ring became a regular target of the press, and Tweed's public image was taking a beating. And when the truth of his corrupt empire made its way to those faithful supporters, it would all come crumbling to the ground.
In 1870s New York City, Boss Tweed oversaw a sprawling fiefdom of shameless corruption and easy money. The Tweed Ring filled 12,000 city jobs and controlled every penny spent for public services. They also ran the city's government.
Tweed was not only the boss of Tammany Hall, but according to the New York Times, he was also the school commissioner, assistant street commissioner, president of the board of supervisors, and chairman of the New York Democratic Committee. And now people began to wonder why the city's treasury was drying up, particularly the reporters already familiar with the Tammany machine.
For the most part, Tweed was seen as a flamboyant curiosity. But the graft became impossible to ignore. Journalists printed story after story accusing him of corruption. But Tweed characteristically dismissed the accusations and they did nothing to sway the support of his loyal base. A bigger problem was that Tweed was the favorite subject of political cartoonist Thomas Nast at Harper's Weekly.
In one of his famous portraits, Tweed was depicted as a huge man in a fancy suit with a bag of money for a head. These drawings did more damage to Tweed's public image than anything else. While many of his constituents didn't know how to read, they did know how to interpret those cartoons.
But cartoons and incendiary journalism alone wouldn't bring down Tweed and his massive network of corrupt politicians. Nope, the breaking point came when their bookkeeper died. In January 1871, James Watson, the county auditor and Tweed's paymaster, was kicked in the head by a horse in a sledding accident. He died a short time later.
By a stroke of terrible luck for Tweed, the position of auditor was appointed by one of the few elected officials in town who wasn't Tweed's crony. When Watson died, Tweed didn't get a say in who replaced him. The replacement auditor, Matthew J. O'Rourke, was not in on the crime ring, and he was now in possession of some very damning paperwork. O'Rourke immediately noticed the books didn't add up,
Incensed by what he saw, he quit his job in protest, but not before copying down a few particularly incriminating ledgers. The tweed ring offered O'Rourke a bribe to stay quiet, which he flatly refused. Instead, he brought the proof of embezzlement directly to the New York Times. On July 29th, 1871, the headline ran in big bold type,
Gigantic frauds of the ring exposed. Tweed knew his time was up. In short order, he started handing over his assets and investments to family members. He wanted to make sure his wife and 10 children could keep themselves afloat when it all sank. Tweed and the Democrats controlled most of New York City politics, but there were some high-ranking Republicans who were just waiting for something like this to break.
and in the state capital Albany, there were even more. In the immediate aftermath of the New York Times exposé, these Republicans and numerous Democrats who had fallen out of favor with Tammany Hall met to discuss the political reform they'd been dreaming of. They needed to strike while the iron was hot. They cut off the city's funding and essentially overturned everything the Tweed Charter had put in place.
Within a few weeks, they formed a new board called the Executive Committee of Citizens and Taxpayers for Financial Reform of the City. It's an elaborate name, but their mission was clear. Rebuild the city's finances and repair the damage done by years of criminal activity.
A new comptroller, Andrew Haswell Green, was appointed. He immediately freed up assets for the strapped city departments and New York could finally breathe a sigh of relief. William Tweed could not. The fateful knock on his door came in early August of 1871. He was charged with larceny and over 200 misdemeanors. He was later released on a million-dollar bail.
He still had friends with money, after all. During his trial, which ironically was held in the courthouse Tweed had built, the jury was unable to reach a unanimous verdict. As a result, Tweed walked free. His freedom, however, was short-lived. The state of New York brought a civil suit against Tweed in November of that year for the same charges, and this time he was found guilty.
He was forced to abandon all of his city positions, resign from Tammany Hall, and relinquish every cent he'd stolen from the city treasury. Without any money to pay what remained of his debts, he was sentenced to 12 years in debtor's prison. Just like that, Tweed went from being one of the city's richest and most powerful men to one of the poorest and weakest.
As a condition of Tweed repaying the hundreds of millions he stole, he was allowed to visit his home once a month, presumably to make arrangements for selling businesses and assets. On December 4th, 1875, Tweed escaped during one of those visits home. He fled to Spain and began working as a sailor.
But in a grimly humorous turn of events, Tweed was turned over to the authorities at the Spanish border because he was recognized from Thomas Nast's cartoons. Tweed was returned to New York and went right back into the slammer, where he would die three years later. With his last breaths, he blamed his downfall on the New York State Attorney General and the governor who rose to power as Tweed went down.
He said with a smile, "I hope they are satisfied now." In the end, Tammany Hall outlived Boss Tweed by nearly a century. Even after being purged of its most corrupt elements, it remained an important fixture in New York City politics. The organization experienced a major resurgence at the turn of the last century.
the ethnic communities it had originally manipulated had morphed into a powerful block of working and middle class voters. This reliable faction allowed Tammany Hall's politicians to once again occupy nearly every office in the city and even extend their reach to the state capital. But the organization failed to endorse Franklin D. Roosevelt in the presidential election of 1932
A mistake it never recovered from. As its influence began to wane, several Tammany-backed politicians were found guilty of, among other things, tax evasion, fraud, and bribery. Once again, Tammany Hall became a symbol of everything wrong with politics.
In the late 1950s, Tammany leader Carmine DiSappio's relationship with Frank Costello, who at the time was the city's most notorious gangster, brought even more scrutiny onto the organization. And in 1967, after nearly two centuries of graft, racketeering, and fraud, on a scale that's hard to imagine, Tammany Hall finally dissolved.
Thank you for listening to Conspiracy Theories, a Spotify podcast. We are here with a new episode every Wednesday. We'll be back next time to explore the mysterious disappearance of a Tammany Hall associate, New York Supreme Court Justice Joseph Crater. Be sure to check us out on Instagram at theconspiracypod.
If you are listening on the Spotify app, swipe up and give us your thoughts or email us at conspiracystoriesatspotify.com. Until next time, remember, the truth isn't always the best story and the official story isn't always the truth.
This episode was written by Anna-Kira Stinson with writing assistance by Kate Gallagher and sound design by Alex Button. Our head of programming is Julian Boirot. Our head of production is Nick Johnson and Spencer Howard is our post-production supervisor. I'm your host, Carter Roy. This episode is brought to you by Hills Pet Nutrition.
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