July 23, 2026

William 'Boss' Tweed | Knives Out | 4

William 'Boss' Tweed | Knives Out | 4
William 'Boss' Tweed | Knives Out | 4
American Criminal
William 'Boss' Tweed | Knives Out | 4

By the spring of 1870, William Tweed had almost complete control over New York – not just the city, but much of the state, too. And with his wealth increasing by the day, he knew that he was nigh untouchable. Money could be used to end political careers, bribe judges to look the other way, or even buy nuisance publications that wouldn’t play ball. But there were a few men who couldn’t be bought. Bill understood plenty about America’s political system, but he didn’t understand that.

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It's just after sunset on a late July day in 1871. At the New York Times building on Park Row, George Jones walks down a quiet corridor.

A few minutes ago, George received a note from a tenant on this floor, asking for an audience with him as soon as possible. As publisher of the Times, George feels a responsibility to take care of the building's tenants.

He stops outside the office of the man in question, a lawyer, and knocks. Seconds later, the door swings open, and George is ushered through the main reception space and into a smaller office with a window looking out onto the street.

A man stands facing the window, his broad shoulders obscuring much of the view. As the lawyer announces George's arrival, the other man turns, and George recognizes him at once. His thin smile, wide chin, and downturned eyebrows are unmistakable.

It's Richard Conley, New York City's comptroller and a member of Bill Tweed's notorious ring. George takes an impulsive step back, telling the lawyer that he wants nothing to do with Conley.

His newspaper has been actively investigating corruption and possible theft committed by Conley and his comrades. Just a few days ago, the paper's editor, Lewis Jennings, came into possession of documents that seemed to prove the ring's guilt.

Before George can get away, though, Conley calls out, asking to be heard. George stops his retreat and stares at the comptroller, gritting his teeth. He waves his hand, indicating that he should go ahead and say what he has to say, quickly.

Sixty-one-year-old Conley takes a small step forward and says that he knows about the documents George has in his possession. He timidly asks, well, begs, really, that George forego publishing them.

He allows that this is a big ask, but says he hasn't come empty-handed. He's willing to offer George five million dollars in exchange for his silence. George snorts at the offer.

It's an astronomical amount of money, adjusted for inflation. That would be about a hundred and thirty-five million dollars today. But George can't be bought.

He studies Connolly for a moment, noticing the nervous way he's wringing his hands, the light sheen of sweat on his forehead.

George tells Connolly that he's sure even the devil himself wouldn't be able to offer him that much money to betray his morals and his city. Still, he's not interested. He bids Connolly and the lawyer a good day and strides from the room.

If he ever had any doubt as to Connolly's guilt, it's well and truly gone. 10 minutes ago, he had plans to go home for dinner. Now though, he heads back down to the newsroom.

They have to get this story published as soon as possible before Tweed and his cronies can find a way to shut them down. From Airship and Evergreen Podcasts, I'm Jeremy Schwartz, and this is American Criminal.

By the spring of 1870, William Tweed had almost complete control over New York.

4:00

Tweedʼs Empire

Not just the city, but much of the state too. As a member of the Senate, he examined every measure introduced in either house of the legislature to make sure that nothing got past him.

No charitable handouts, no valuable sinecure, no capital infrastructure, without the proper price being paid. In this case, the proper price was an extra 30 percent on top of any bill paid by New York City or County.

Vendors were expected to artificially inflate their quotes, and then direct the extra money to Boss Tweed's infamous ring, Oakey Hall, Richard Conley, and Peter Sweeney.

Bill had gathered these men around him to consolidate his already powerful position. He himself was both an elected official and the head of Tammany Hall, the Democratic Party's chief operational unit within the state.

Oakey Hall was the man he chose to fill the empty mayor's office, after Bill had the previous one elected governor. Conley was the city's comptroller, which basically meant he was the chief financial officer and auditor for New York.

Peter Sweeney was a former district attorney and had one of the best strategic and legal minds in Tammany Hall.

In April 1870, Bill ran through a new charter to remove New York City from control of state lawmakers and hand it directly to the members of the ring. And the city cheered him for it.

No one knew that Bill's ultimate goal wasn't the improvement of New York or the betterment of its people. He just wanted to make it easier to raid the piggy bank. And with his wealth increasing by the day, he knew that he was nearly untouchable.

Money could be used to end political careers, bribe judges to look the other way, or even by nuisance publications that wouldn't play ball. But there were a few men who couldn't be bought.

Bill understood plenty about America's political system, but he didn't understand that. And that failure, as much as his greed, would be his downfall. This is episode four in our four-part series on William Boss Tweed.

Knives Out. It's mid-April 1870, about a week after Bill Tweed's new charter was signed into law by the governor. At Delavan House, a six-story hotel in Albany, Bill's hosting a meeting of his three most trusted allies, Hall, Sweeney, and Connolly.

Bill keeps a suite of his own at the Lavish Hotel, using it when he's in town to do his duties as state senator. He sometimes invites fellow lawmakers there for teter tets, which often involve hefty bribes.

But tonight's agenda is more formal, so Sweeney is hosting in his suite instead. Earlier this year, this is where Sweeney himself drafted the charter that redefined who has control over New York City. Now, the Tweed ring are about to do it again.

Soon after New York City's new charter goes into effect, Bill and his accomplices meet behind closed doors to finalize the tax levy bill, which sets the city budget for the year. They have two main goals with this bill.

The first is to extend funding to Catholic parochial schools. This is in defiance of a rule outlawing public funds being used for religious institutions. But it will be a boon for New York's sizable immigrant population.

Essentially, they're doing something nice for their voter base. The second, much bigger goal is to close their collective fist around the city with several key measures. The first makes the position of comptroller and appoint of one.

Until now, comptrollers have been elected. With this change, the mayor chooses who's comptroller, and they hold the office for five years. The next measure formally strips the city aldermen of their financial oversight power.

Essentially, shutting them out of the city's budgetary concerns. It also means aldermen won't be able to demand graph payments of their own by withholding their votes.

And finally, they add wording to the bill that eliminates the County Board of Supervisors. And it's that last bit that gives the Tweed ring the opportunity to do something even more devious.

You see, the Board of Supervisors is sitting on a bunch of unpaid bills from the last couple of years. And we're talking over $6 million worth of charges here.

Oakey Hall suggests that they pay off those bills now, so that everything is wiped clean once the Board no longer exists. And that makes sense, right? Except that these guys aren't really interested in tying up loose ends.

They want the money that can skim from the top of all those padded out bills. Remember, Bill Tweed didn't invent the act of artificially inflating costs and taking the extra under the table. Other politicians have been doing it for years.

So, all these unpaid invoices are just sitting there plump and juicy and ripe for the taking. But even that's not enough. They decide that they'll inflate each bill by another 50% before they disperse the funds.

Each member of the four-man ring will take a fifth of that extra money, with the rest being split among two other men essential to pulling off the scheme.

James Watson is a county auditor who works under Conley at the Comptroller's Office, and Albert Woodward is a clerk for the Board of Supervisors. Or he was until Bill and his friends eliminated it.

Bill trusts both men completely, and it's their job to distribute the funds to the vendors. They also ensure that the extra money is then funneled through multiple accounts and eventually lands in those belonging to the ring members.

Now, obviously, all this money has to come from somewhere, right? There isn't just a bottomless pit they can pull cash from to hand out whenever they want. But no one wants to raise taxes either.

That'll make voters angry, and it might make people ask questions about where the money's all going. So, instead, Conley starts borrowing money on the city's behalf, mostly by selling bonds to banks and overseas investors.

While all of this thievery is going on, Bill and the Ring are still running the city. Together, they authorize infrastructure upgrades around New York, including widening key thoroughfares and constructing brand new roads.

But even in this, there's an ulterior motive. Because with all his millions of pilfer dollars, Bill buys up land and parts of the city right before improvements are announced, then watches the value of his land investments rise.

This isn't something that goes unnoticed, mind you. The New York Times even prints a piece pointing out that whenever Boss Tweed buys land, the neighborhood is in for some kind of upgrade in the coming months.

But by this stage, Bill's just seen as one of the city's wealthiest men, and people don't really question where that money comes from. And if they did, he can point to his involvement in numerous successful ventures.

He's a director of the Erie Railroad, the 10th National Bank, and the New York Printing Company. He sits on the board of the Brooklyn Bridge Company, the 3rd Avenue Railway Company, and the Harlem Gaslight Company.

He's the president of the Guardian Savings Bank, proprietor of the Metropolitan Hotel, and is the third largest land owner in New York City. He even owns his own newspaper, The Transcript, which he bought in 1869.

Now, it receives a healthy amount of advertising money from the city. Not all of these positions are things that Bill's actively involved in.

In fact, he bribed or sweet-talked his way into some of them, and was likely handed others because of the red tape he could help clear. And there's not a lot of red tape that Bill Tweed couldn't deal with these days.

But like I said earlier, there are some things that he can't control. And they are about to start causing him a lot of trouble. In June of 1869, almost a year before the Tweed ring enacted its new charter, Henry J.

12:45

Times Investigation

Raymond died of a heart attack. He was co-founder of both the Republican Party and the New York Times. Following Henry's death, his partner George Jones took over as the paper's publisher.

Then, in January of this year, George hired 32-year-old British journalist Lewis Jennings as editor.

Now, both George and Lewis side with the Republican politicians in most things, so it's unsurprising that they're opposed to the actions of Bill Tweed in the ring.

But it's worth pointing out that Lewis' personal anti-Irish bias might play a role in his dislike of the leader of Tammany Hall, an institution that by 1870 has become almost synonymous with the Irish community.

But whatever their true motivations, what's important here is that the two men helming the New York Times have been eager to go after the Tweed ring for months, especially when they see the cartoons of Thomas Nast appearing in Harper's Weekly.

When he turns his pen to the ring, Nast's cartoons depict Tweed with his protruding belly, receding hairline and downturned mouth. Nast is one of the only people in the entire city actively drawing attention to Tweed's corruption.

Most of New York's other news publications have lucrative deals with the city to publish government updates each week. And few publishers want to risk that income, so instead they sing the praises of Tweed, Hall and the rest.

As for the Times, George and Lewis have been held back, at least in part, by their board of directors. One of its three members is a guy named James B. Taylor, and he's a co-owner of the New York Printing Company.

Well, who's one of the other co-owners, you ask? Bill Tweed. And while the ring is in power, the company is making millions of dollars from public advertising bought by the city.

So it seems likely that Taylor has been using his position at the Times to keep any mention of Tweed positive. But late in the summer of 1870, James Taylor dies. And not long after that, the Times makes its first open assault on Bill Tweed in print.

The editorial in question asked Bill for advice on how one can go from having spent all of one's money on a failed political campaign to having millions of dollars in just five or six years.

The article goes on to allege that people on the street are whispering about Bill Tweed's corruption. And that's only the first shot fired. After this opening salvo, the Times swerved slightly.

It is by and large a Republican newspaper, so repeated attacks against Tweed and his Democrat cronies could be dismissed as partisan grumblings. Most newspapers are full of them.

Lewis knows this, so he turns his attention to the numerous Republican politicians who've sided with Tweed in the ring. Some of them have accepted positions within the city government.

Others have no doubt accepted bribes in exchange for their votes in Albany. Their complicity has allowed the ring free reign over the city and its money. Now the Times goes in hard, attacking what's essentially its own party.

This tactical decision makes it difficult for Tweed or any other Democrat to denounce the accusations. It also means Tweed can continue ignoring the editorials for a little while longer.

But in the lead up to the 1870 election, the Times makes a public request that can't be ignored. See, as comptroller, Richard Connolly is expected to issue a report on the city's finances at the start of each year.

But he never delivered one for 1870. And the Times demands that he allows someone to inspect the books. Well, that's something that Tweed is all for.

So he appoints a special committee of investigation to do exactly that. Members of the committee include multimillionaires John Jacob Astor, Moses Taylor and Marshall O. Roberts.

This group of men spend about six hours looking at the city's ledgers and accounts, which seems like a short amount of time to conduct a thorough investigation. But they're not interested in thorough. They're just doing as Boss Tweed tells them.

He's the one position to grant political favors after all. So Astor and friends just look at the material Connolly lays out for them, see that the numbers all tally up from column to column, and that's about it.

They don't dig into where the money is going or how much is being spent. They published their report on the eve of election day, declaring erroneously that they've inspected everything and found nothing incriminating.

They even declared that the city's debts will be wiped out after 12 years under Connolly's management. But not everyone buys what the Committee of Investigation is selling. A few months ago, William Copeland started seeing red flags.

He's been working in the comptroller's office for most of the year. He got the job thanks to his friend Jimmy O'Brien, who's a longtime member of Tammany Hall.

Almost immediately, Copeland noticed that figures in the books just weren't adding up, and that the city seemed to be paying ridiculous amounts of money for just about everything. Nothing should be costing as much as they're paying.

He went to Jimmy to tell him about his concerns, and Jimmy asked him to make secret copies of anything suspicious.

Jimmy used to be the New York County Sheriff, but after he opposed Bill's new charter for the city, he was frozen out of Tammany's inner circle. Now, he's gathering intel to use against them.

And while that's happening, some of Tweed's most devoted lackeys decide to show him just how devoted they are. Headed by a judge, Shandley, a committee is formed to raise funds to erect a statue of Bill.

Men who benefited from Bill's rise to power give readily to the cause, but a donation of just nine cents has the biggest impact of the campaign. That's how much Thomas McHugh sends, along with a letter to The Sun newspaper.

He's a poor working man who can't afford more than that, which he says is because Boss Tweed has defrauded the public of millions of dollars.

Thomas ends his letter saying he hopes the statue is built, so that his children can point to the man who robbed them of their futures. Shortly after this letter appears in The Sun, Bill seems desperate to do some damage control.

So when he's asked to give to a fund set up to buy Christmas dinners for needy families, he pledges $5,000. When he's needled into giving just a little more, he adds a zero, upping his donation to 50 grand.

Adjusted for inflation, that would be over 1.2 million today. But to Bill Tweed, it's nothing. Unfortunately for Bill, his largesse backfires.

In The Times, Louis Jennings writes about the donation under the headline, some stolen property returned. And then he goes on to accuse Bill of making $75,000 to $80,000 a day.

Then he alleges that this kind of generosity is designed to keep people from asking questions, to stop anyone from wondering where Bill Tweed got all that money from.

And despite Bill's best efforts to squash them, those sorts of questions will be answered soon enough. It's January 31st, 1871 in New York City. A week ago, County Auditor James Watson was trampled by a horse in a freak sleigh accident.

At first, it looked like he'd be fine. A doctor put a bandage on his head, and he came home to his Madison Avenue mansion to rest. But things took a turn, and his words started getting around that James might not make it.

People started showing up at the family home. These men are mostly members of Tammany Hall, and there's been at least one somewhere near James' bedroom for days now.

Whenever someone arrives to visit James, the men stand up and draw close to the door. It's like they're listening in on whatever conversations are happening around the house. But the Watsons hardly care about that now.

James' closest family members are in the room with him as he takes his last breaths.

In the still quiet that follows James' passing, the only sounds come from these men muttering to one another in the hall as they put on their coats and head for the front door. They've done what they were ordered to do.

They ensured James Watson made no deathbed confessions about what he knows. And now they're heading back to Boss Tweed to tell him that he has nothing to worry about. The death of James Watson is troubling for Bill Tweed.

Not only has he lost a man he might call a friend, he's also lost a trusted ally in his years-long plot to swindle the people of New York.

James kept private copies of all the transaction Tweed's ring oversaw, and was the one to move money through various accounts once the city released funds. He was a valuable cog in Bill's machine. And now he's gone.

But perhaps, Bill thinks, that's a good thing after all. With the New York Times coming at him with some new accusations every week, one less person who has to keep their mouth shut is probably for the best.

After a while, his mind drifts to other concerns. There's plenty he has to juggle to keep his operation running smoothly, and that includes the occasional personal engagement.

At the end of May, Bill's daughter, Mary Amelia, gets married in a lavish ceremony, followed by a party like the city's never seen. It's a happy day for Bill and his family.

But the next morning, at least one journalist writes a detailed list of the extravagant gifts showered upon the happy couple by Bill, his political allies, and the many wealthy wedding guests.

The estimated value of these gifts printed in the Herald is $700,000. If you adjusted that amount for inflation, it would be $19 million today on gifts.

As a reminder, it was just 10 years ago that Bill spent his entire $100,000 fortune running for New York County Sheriff. He had nothing left after that race.

Now, he's one of the richest men in the city and people come to his daughter's wedding to pay tribute to him. And for the most part, no one's talking about this. For years, the city's newspapers have benefited from doing business with City Hall.

Speaking out against Bill or even asking questions could make those lucrative advertising contracts disappear. So, when people come directly to news editors with supposed proof of the Tweed ring's corruption, they're hesitant to touch it.

Just look at Matthew O'Rourke. He's spent the last few months working in the Comptroller's office following James Watson's death.

On the same day Bill's daughter got married, he quit and has spent the last few weeks calling on different editors with evidence that something's not right.

The document he offers to a number of newspapers show that the county has been renting a collection of 10 old stables for a total of $85,000 a year.

On paper, the stables are marked for use as armories, but really, they've never been used for anything. Still, the county authorized over $400,000 worth of repairs to the buildings. But there's no evidence that those repairs were ever even done.

It's a lot of taxpayer money being paid for empty buildings. And who is the county renting those stables from? Members of the Tweed ring.

Still, Matthew O'Rourke seems to have trouble finding anyone interested in printing what he's got. So Bill's in the clear for now. Of course, Matthew's not the only one who's gathered evidence of Bill's crimes.

It's been almost a year since William Copeland came to his friend Jimmy O'Brien to tell him about what he's seen in the city ledgers. Copeland spent months making copies of just about anything that came across his desk and brought them to Jimmy.

Now Jimmy brings them directly to the Tweed ring, hoping to make a deal. Jimmy was one of the people inside Tammany who tried to thwart Bill's plans to consolidate his control over New York.

As punishment for this rebellion, Bill ensured Jimmy lost his bid for re-election to the Sheriff's office. That cost him at least $350,000 in fees he could have collected on the job.

If Tweed and his cronies agree to pay him for that lost money though, he says he'll destroy the copies of the ledgers. The amount Jimmy's asking for is a pittance compared to how much money Bill and the others have.

But for whatever reason, they decide they're not willing to part with that sum to buy Jimmy's silence. So Jimmy walks into the New York Times building and hands the evidence to editor Louis Jennings.

Two days later, Matthew O'Rourke does the same thing. And when word of this gets back to the members of the Tweed ring, they start panicking. Suddenly, parting with 350k isn't looking like such a hardship.

Bill dispatches Connolly to deal with the Times, ordering him to offer publisher George Jones $5 million to not print the ledgers. But George won't be bought. He walks out of Connolly's attempt to negotiate an acceptable bribe.

Around the same time, someone within the ring, maybe even Bill, sends a lawyer to take care of Thomas Nast. His cartoons have been their own brand of trouble lately.

Because while the reporting in the New York Times contain specific accusations, the Nast drawings leave a more lasting impression. What's more, anyone can understand Nast's cartoons, even if they can't read English.

And that includes plenty of Tammany Hall's strong base of immigrant voters. Anyway, a lawyer approaches Nast, and tells him that a very wealthy man wants to pay to send him overseas to study art under the European masters.

A man with Nast's talent needs to be nurtured, he explains. Nast walks away. But then a week later, an officer from the Broadway bank appears on his doorstep.

He tells Nast that he's heard about this offer, and advises him to accept. Continuing to prod at the Tweed ring will only bring him trouble, he warns, before telling Nast that he could probably ask for as much as 200 grand for the trip.

When Nast asks the banker if he thinks he could get 500, the man nods vigorously and tells him that of course he can. 500,000 in gold. But Nast turns him down, says he's made up his mind to see Tweed and the others put in jail for their crimes.

The banker shakes his head and goes to leave telling Nast to be careful. There's every chance that he could end up in a coffin before he puts those men behind bars.

The desperate attempts Bill and his buddies make to try and silence the New York Times and Thomas Nast start to make sense once the Times starts publishing records from the copied ledgers.

29:11

Evidence Published

Now the figures don't all show money flowing directly from the city's accounts into Bill's or Conley's, but they clearly prove that the city's been overpaying for services and products, often to the same few firms over and over and over again.

Here's an example. A plasterer was paid $138,000 for two days work on the New County Courthouse. Two days!

His total bill for various jobs is a little under $3 million. Again, if we adjust that number for inflation, that would be about $77.5 million today. And that's just the tip of the iceberg.

You remember Ingersoll and Company? They're who Bill used to make a killing from some benches he bought from a community hall, and then sold them back to the county at a huge markup.

The owner of the firm was friends with Bill's late father back in the day. Well, the record showed that he's been paid close to $5.7 million to furnish the new courthouse.

The New York Times continues publishing the evidence in daily installments, keeping the public outrage for a couple of weeks.

The story is so popular that once they put out everything they have, they release a special supplementary publication that covers the entire story from start to finish, in both English and German, to ensure that the city's large German population

knows what's going on. And through all of this, Thomas Nast has been lampooning Bill in the ring with more piercing caricatures.

His cartoons are the talk of the town, with Harper's Weekly circulation soon jumping from 100,000 to 300,000 copies per week. Gradually, the rest of New York's press abandon their defense of the ring. The tide is clearly turning against Bill Tweed.

And editors throughout the city know better than to stay on this particular sinking ship. Even Bill recognizes that the situation is dire.

With his grip to power looking tenuous, he starts to transfer ownership of his vast real estate holdings to his son.

Still, although Bill's corruption is on display for everyone to see, stopping him and his accomplices from doing more damage isn't gonna be easy. They've consolidated their power so completely that there's no simple way to check them.

But it is doable. In early September, a public meeting is held at the Cooper Union on Third Avenue. Anger is in no short supply at the meeting.

With more than one person calling out for Bill and the others to be hanged. But after the furious roars of approval die down, calmer heads prevail. They don't need to resort to violence to deal with this.

The assembly appoints a 70-man executive committee to act on behalf of the people, to make sure that Bill Tweed and anyone who's helped him is prosecuted.

A couple of days later, this committee files a lawsuit to prevent the office of the mayor, as well as any position beneath him, from collecting taxes. The suit also seeks to stop the payment of any city funds to anyone for any reason.

It's a solid first step, in theory. But as the city wakes up to what's been going on, lynching suddenly seems like it might be the easiest way to deal with the problem after all.

Bill's packed every level of the government, from the daily street workers all the way up to the highest courts. This includes Judge George Barnard, who will be presiding over the case brought by the committee.

He's a long time friend of Bill's, and it's anyone's guess whether he'll side with his buddy or the public.

When it comes down to it though, Judge Barnard grants the restraining order, and the shock of this betrayal takes its toll on 48-year-old Bill. People around him report that he starts having occasional hysterical outbursts in the wake of the ruling.

He himself will later admit to contemplating suicide around this time, too. But while Bill's spiraling, his accomplice, Mayor Oki Hall, takes action. Or he tries to anyway.

He writes a letter to Connolly asking him for his resignation, then reads it to him at the ring's regular lunch meeting. Hall says that as comptroller, this is all Connolly's fault.

It's hard to be sure of what Hall's thinking is here, but given that there's still no hard evidence that any of the ring members are receiving funds directly from the city, he might be hoping that sacrificing Connolly will appease the masses and

everything will die down. But Connolly refuses to resign. He can see that his former allies want to pin this whole thing on him. And if that's their plan, he's not going to make it easy for him.

The next morning, Oki Hall sends his letter to the press, making his demand for Connolly's resignation public. But all this does is let everyone know that the Tweed ring is divided. But here's the thing, though.

Hall, Sweeney and Bill can try to voice the blame on Connolly all they like, but they snookered themselves.

Remember how they did away with the Board of Supervisors, took away most of the powers of New York's aldermen, and made the comptroller a position by appointment?

Seemed like a great idea at the time, because it made all of them harder to remove from office. But that was when they only anticipated hostile attacks from political rivals. They never expected to be turning on each other.

That lack of foresight is the final domino that'll bring Bill Tweed's empire crumbling to the ground.

35:32

Ringʼs Collapse

It's September 18th, 1871. It's been about two months since the New York Times first began publishing evidence of Bill Tweed's corruption.

Mayor Oakey Hall is sitting at his desk, head in his hands, when his secretary knocks on the door and then rushes in without waiting for a response.

Hall looks up, angry to be disturbed, but he takes the note as secretary hands him anyway, his eyes scanning the paper quickly. He can feel his heart start to race as he reads. It's a letter from Richard Connolly.

He writes to inform the mayor that he's nominated one of his deputies to carry out his duties as city comptroller. There's an obscure provision written into the law that allows him to designate his own temporary replacement, and he names Andrew H.

Green as that person. Hall drops the letter on his desk, his hands flying up to the side of his head where his fingers curl into his hair. Shaking with rage, he yanks, pulling small clumps out.

The hairs fall from Hall's grip, landing on Connolly's letter on this sign of betrayal. After OK.

Hall turned on Richard Connolly and publicly demanded his resignation, Connolly went to see Samuel Tilden, a lawyer, power broker within the Democratic Party and longtime rival of Bill Tweed.

Tilden is also a member of the Committee of Seventy, assembled to seek justice for the Tweed Ring's crimes, and Connolly's hope was that by agreeing to cooperate, he could buy himself leniency.

It was Tilden's idea to have Connolly step aside for one of his deputies, one of Tilden's allies. That way, the Committee of Seventy would have complete access to all records within the Comptroller's office. But OK.

Hall refuses to accept Andrew Green as the new Comptroller. He issues a memo to all heads of department ordering them to ignore any directives coming from either Connolly or Green.

He then tries to appoint a Comptroller of his own choosing, a former Democratic presidential nominee. But his choice refuses to accept. And by this stage, Hall seems to accept that he's lost this round.

Andrew Green gets to work right away. First, he does something virtually unheard of in government at the time. He sends out an edict to all city and county employees, ordering them to actually show up to their jobs every day.

The time of the sinecure is over. Government employees are also forbidden from accepting payoffs or kickbacks. This is the last stop for the gravy train.

Greene then instructs the clerks in the Comptroller's Office to count how much cash the city has in its vaults. There's 2.5 million, but come November, New York needs to pay 2.7 million in interest to their many creditors.

And that's to say nothing of the many unpaid bills the city is accumulating. The restraining order against the use of city funds has meant the city's employees have been going without pay for weeks.

School teachers, laborers, clerks, police officers, all people who are owed several paychecks, and plenty of them with families to support. That's the most pressing issue.

But in a turn of events few people could have ever seen coming, a group of banks steps in to save the day.

The heads of 10 of New York's largest banks come together to advance the city an unsecured loan of $500,000, based solely on Andrew Green's handshake.

With the most pressing issue taken care of for now, Samuel Tilden pays a visit to the Broadway bank. This is where Bill Tweed, the other members of the ring, and some of their closest associates all have accounts.

Tilden and a team of analysts go through the bank's records, but can't pick up the trail of money after it leaves the government accounts. That is until they find the Kaiser warrants.

The details are complex, but essentially Tilden and his team find a set of warrants or payments issued for work on city armories and the now-infamous county courthouse. All of these slips of paper feature the initials EAW or the name EA.

Woodward, which leads them to Edwin Woodward, who was once Bill Tweed's clerk at the Board of Supervisors. He's also one of the two men Bill trusted to take care of moving the ring's payments around. The other was the now-deceased James Watson.

Looking at Edwin's personal accounts, Tilden and Co. trace money moving from government accounts into Edwin's, and then bouncing around a series of intermediaries before finally landing in Bill Tweed's and those of his accomplices.

It's exactly the evidence that the Committee of 70 has been searching for, and Tilden takes it directly to New York Governor John Hoffman. An arrest warrant is issued for Bill Tweed soon after this.

And as news of the warrant flits around the city, Bill holds up in his law office on Duane Street, burning his personal records in the fireplace. But that won't save him now. When Bill Tweed is arrested, his bail is set for $1 million.

That would be $27 million today. The amount is put up by a group of wealthy businessmen and close acquaintances of Bill's, which leaves him free to continue his campaign for re-election. Oh, did I forget to mention?

Bill managed to be nominated for the state senate again, even in the midst of the scandal. So he announces to the world that he's innocent of the fraud charges against him, and vows to win a senate seat too. And he does just that.

He wins the election in November 1871, thanks in part to his personal popularity and history of making large public donations to charities. But Tammany Hall, the political group he's become the face of, takes a battering with the voters.

As for Bill's accomplices, they abandon him one by one. Richard Conley had already turned against him before Bill's arrest. And by mid-November, Oakey Hall starts cooperating with the Committee of 70.

Conley officially resigns his post as comptroller, and Hall agrees to appoint Andrew Green as his replacement. But despite his cooperation, 61-year-old Conley doesn't escape punishment.

He's arrested on November 25th, and no one steps forward to pay his bail. He has the money himself, but he just can't use it, or else it'll be seized by the authorities.

Peter Sweeney flees the country before any warrants are issued for him, as do some of the people who enabled and benefited from the Tweed Ring's corruption. Furniture maker JH.

Ingersoll, bookkeeper Albert Woodward, and even Andrew Garvey, who made millions as the Ring's plasterer of choice for the county courthouse. As for Bill, he's indicted by a grand jury, re-arrested in mid-December, and makes bail once more.

This time, just $5,000. By the end of the year, he's resigned all of his public and private offices except for his Senate seat. That he wants to hold on to.

A few days later, Connolly finally makes bail, and he hops a ship to France, never to return. Mayor Oakey Hall is a different story. Like Bill, he's arrested and is brought to trial in October of 1872.

But when a juror dies, they have to start again. The second jury can't reach a verdict, and he's eventually acquitted at his third trial. But his political life is over.

He'll eventually return to his career as a lawyer and spend time working as a journalist. Bill's trial doesn't get going until January 1873. There are 220 charges against him, and the jury can't reach a verdict.

At his second trial, though, he's convicted on 204 of those charges, and he's ordered to pay a fine of $12,750. And he's sentenced to 12 years in prison. But this sentence is eventually reduced to just a single year behind bars.

When he's released, the state of New York files a civil suit against Bill to claw back the $6 million he's alleged to have stolen. Unable to pay the money, he's locked up in Ludlow Street jail, which is essentially a debtor's prison.

From there, Bill's allowed home visits for dinners with his wife and grown children, the ones he never had time for during his career. And it's on one of these visits that he decides to make his escape.

He sneaks out of his family home and boards a boat to Cuba. But his final destination is Spain. The US government finds out where Bill's heading and sends word to the Spanish authorities to look out for him.

Unluckily for Bill, the cartoons of Thomas Nast aren't popular only in New York. He's recognized almost as soon as he arrives in Spain, thanks to Nast's many drawings of him in the recent years. He's put on a US warship right back to America.

By this point, Bill's a broken man. After a life of excess, his health has finally caught up with him. He's in his early fifties, but he's growing weaker every month and desperate not to spend any more time in jail.

So, in July of 1877, he agrees to testify before a special committee of New York's aldermen about how the Tweed ring operated. His expectation is doing so will earn him his release.

But although he speaks in great detail about his life and crimes, Bill Tweed doesn't win the freedom he's so desperate for. The Attorney General insists that Bill's testimony offered nothing new to the state and wouldn't result in further arrests.

As for the state's newest governor, Samuel Tilden, he's inclined to agree. He makes no move to offer leniency to his former Democratic Party rival. After that, Bill's hopes of freedom die.

He spends the last months of his life accepting visitors to his cell, waving to people on the street outside his window and otherwise resigned to his fate. On April 3rd, 1878, Bill turns 55. But it's not a happy occasion.

He's feverish, suffering from bronchitis, pneumonia and kidney failure. A little before noon on April 12th, he dies. In the hours after Bill Tweed's death, news of his passing spreads through the city he once ruled.

Some people insist that it's a hoax, that Bill's faked his death in another bid for freedom. But it's true. Boss Tweed is gone.

His legacy, though, that lingers. In the years and decades after William Tweed dies, his figure is twisted and pulled, molded to suit all kinds of political villainy. In the end, the collective memory of him is that of the archetypal political boss.

His weight and figure are mentioned almost as often as the details of his crime, as if his size was some kind of revealing tell about his true nature. It's true that Bill Tweed was a greedy man.

He craved wealth and comfort, and the power that enabled both of those things. He took what he wanted, barely sparing thought for how his actions would affect the city he claimed to love.

At the same time, he understood that his power was derived from the people whose money he stole. So he gave generously to charity, and ensured that the government did too.

He oversaw capital improvements to New York, helping to modernize the city during his time at the top. He didn't invent the kind of corruption that made him rich. He simply perfected it.

Like other politicians of the time, he often won office through showmanship, cheating and bribery. And when he was caught, he refused to admit his guilt. You have to wonder what a man like that could have accomplished if he played by the rules.

Would his legacy then be as one of the country's great political minds, or was it only his corruption that allowed Bill Tweed to succeed? And if that's the case, what does that say about the great American experiment? I'll let you decide.

From Airship, this is the final episode in our series on William Boss Tweed. On the next series, how a former heroin addict built one of the most lucrative drug empires New York has ever seen, and how it all fell spectacularly apart.

We use many different sources while preparing this episode.

A couple we can recommend are Boss Tweed, The Story of a Grim Generation by Dennis Tilden Lynch, Boss Tweed, The Rise and Fall of the Corrupt Paul Who Conceived the Soul of Modern New York by Kenneth D.

Ackerman, as well as Reporting in the New York Times. This episode may contain reenactments or dramatized details. And while in some cases, we can't know exactly what happened, all our dramatizations are based on historical research.

American Criminal is a co-production of Airship and Evergreen podcasts. It's hosted, edited and executive produced by me, Jeremy Schwartz. Audio editing and sound design by Sean Ruhl-Hoffman.

Music by Thrum. This episode is written and researched by Joel Callan. Managing producers are Emily Burke and Sarah Willgrube.

Executive producers are Joel Callan and Lindsey Graham.