July 30, 2026

William 'Boss' Tweed | How History Made the Man | 5

William 'Boss' Tweed | How History Made the Man | 5
William 'Boss' Tweed | How History Made the Man | 5
American Criminal
William 'Boss' Tweed | How History Made the Man | 5

If the story of William Tweed has taught us anything, it’s that corruption in politics is nothing new. But nor is corruption the only thing that affected the course of Boss Tweed's career. We're joined by historian, lawyer, and author Kenneth Ackerman to talk about the life and legacy of William Tweed, the impact of the Orange Riots on New York City, and the way history echoes through the ages.

Listen to all 4 episodes of 'William 'Boss' Tweed' wherever you get your podcasts, or to get early, ad-free access to the entire season first, subscribe in Apple Podcasts, Spotify, or at ⁠⁠Americancriminal.com⁠

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From Airship and Evergreen Podcasts, I'm Jeremy Schwartz and this is American Criminal. So by now, it's probably clear to you that corruption in politics is nothing new. If the story of William Tweed has taught us anything, it's that.

Bribes from businessmen, bribes to other politicians, secret kickbacks for approving contracts, nothing was off the table even 150 years ago.

And these holes in the political system, as well as in the laws that were still being written, allowed plenty of men to accumulate unchecked power. But rampant corruption wasn't the only reason people called William Tweed Boss.

Nor was it the only thing that contributed to his downfall. Okay, so you probably noticed that history is never simple. And as much as we try to include every important chapter of a person's story, we can't always get into the weeds on everything.

That's why we enlisted the help of someone who knows the life of William Tweed very well. Kenneth Ackerman is a historian, writer and lawyer.

And his book, Boss Tweed, The Rise and Fall of the Corrupt Paul, Who Conceived the Soul of Modern New York, was an invaluable source of information when we were putting the series together.

Ken was kind enough to sit down with producer Joel Callan to talk about the influence and legacy of William Tweed, the major events that shaped his life and successes, and the pieces of the puzzle we couldn't quite get into in our full series.

Ken, first of all, I'm very excited to get to chat with you because I really enjoyed reading your book all about Boss Tweed. It's such a fascinating time in American history.

But before we dive into the Boss Tweed a little, I wanted to get to know you a little bit more because you've published a few books now. But you're not a full-time historian or writer. You're an attorney, right?

Yes.

I've been a lawyer for 50 years, but I don't practice as much as I used to. I live in the Washington, DC suburbs in Foster's, Virginia. And I came to Washington to go to law school in 1973.

It was the height of Watergate. That summer were the Irving Committee hearings. And I was very much drawn by the politics, all the stories, the drama.

And so I came to Washington to go to law school. About halfway through law school, I started working on Capitol Hill for one of the congressional committees.

And for the next 25 years, I worked in different capacities as a lawyer for different government agencies. I did two rounds of jobs on Capitol Hill for different senators and committees. And then I worked in a couple of different government agencies.

And then I left government in 2001 and joined a law firm, but realized I didn't really enjoy actual practicing law that much. So I went on a spree of book writing. And ever since, I've kind of divided my time between those two worlds.

So yes, I'm a lawyer and a writer, and I wax and wane between which one I'm doing more.

I love that you're able to sort of pick and choose and go, you know what, I'm a little tired of this area of my life right now, so I'm going to go over here and do this for a while. I like that.

It took some negotiation with my law firm and clients, but it worked out.

Okay, good. I'm glad. It worked out for us too.

Because, yeah, your book was a fantastic read, and it was very helpful for our research.

4:11

Early Historical Works

But Boss Tweed wasn't your first book. Your first book was published in 1988.

Correct.

And it was about an incident from 1869 when, to make a long story short, two speculators tried to corner the US gold market. What was it that drew you to that specific incident and wanting to write a book about it?

This is a little bit of a long story, but I'll try to tell it very quickly.

During the 1980s, when I was a very young lawyer, I worked for a government agency called the Commodity Futures Trading Commission, which oversees the derivatives markets, basically the commodity futures markets.

And during that time, I was assigned, as were many other people at the agency, to what was the premier financial scandal of the era, which was the Hunt Brothers, and their attempt to corner the silver market, which occurred in 1980, their alleged

attempt to corner the silver market. I was involved in one of the investigations of that incident. And on our group of lawyers, I was assigned to write the report. And what resulted was like an almost 700-page report.

It was a very complicated affair. But I got my writing juices very worked up on this story. It was a wonderful story, just of intrigue, of the strategies of the financiers on the different sides, the interplay of the markets and the regulators.

But when the report was ready to come out, I was very proud of this report I put together, the agency lawyers looked it over and they told me that it was full of confidential trading information and that it had to be redacted.

So I had to spend several days with a black magic marker because that's how you redacted things. Basically, taking out all of the good parts, all of the interesting parts, because that was private parts. And it was a very frustrating experience.

And after that, I decided I really wanted to find a way to tell this story in a way that I wouldn't get sued very legitimately by people on different slides.

So I happened to come across, I was genuinely aware of the story of Jay Gould and Jim Fisk from high school American history. And so at one point, I went into the Library of Congress. I lived on Capitol Hill back then in Washington, DC.

And I went into their newspaper reading room and pulled up a copy of the New York Times from the day of the market crash in 1869 and started reading. And it was a very eye-opening experience.

Newspapers back in the 1860s, not just the Times, but the Tribune and the Sun and the others, they were written in a very alive, breathless, in-the-moment style. And it just brought me into that world.

And the Fisk and Gould story was such a good analog, you know, a set parallel piece to the Hunt brothers and the silver market. Two guys cornering the New York City metals market.

But it also had an extra twist to it, because in the story of the Hunt brothers, a lot of that evolved government regulation, the role of the people supposedly in control of the markets, the SEC, the CFTC, the Federal Reserve, or the Treasury

Department. But in 1869, when the Fisk and Gould were doing it, there was no such thing as regulation. There were no rules. It was the Wild West.

And so the level, the intensity of the strategies and counter strategies and game play, and the level of the story was very, very intense. And so that was where that book came from.

I wrote it up as a magazine article, then I got the chance to show it to a book agent and he sold the book.

There's a couple of things I wanted to come back to on that. The first is the way that newspapers used to be written in the 1800s, even up until mid 1900s. The writing style was so much more pros than it is today.

And I love going back through historical newspaper archives when I'm doing deep dives for the show and finding these beautifully written pieces that today would just be very short and to the point and just facts.

But they were cramming as many words they could into the newspaper like inches that they had, which I just find fascinating.

So I'm glad you brought that up because I think it's something that not a lot of people realize is when you go back through the newspaper archives, the way that these stories are written is so evocative.

Well, with the Tweed story that we'll get into, the editor of the New York Times who was brought in when they started their investigation of Tweed was a man named Lewis Jennings who had written for the British tabloid press and he was brought in to

New York and he had that sensitivity. So his prose was described as acid. If you were on his wrong side, he would go after you. Some of the other papers, the New York Sun in particular became one of my favorites.

It was almost like watching cable TV, cable TV news. The reporters would go to the scene of an event. They would try to find the key players and interview them on the spot and get down their reactions for Beto.

So it's almost like watching live interviews of the direct players in a very exciting moment, and getting it very unvarnished, unfiltered.

Yeah. And it's interesting reading these historical pieces because something I like to do in our show is try and include like people's ages and because then you can understand the passage of time a little better.

You can understand where they maybe were in their life. And I think I spent a couple of hours one day trying to figure out how old one person was when he died for this series. And I couldn't do it.

I couldn't find his grave anywhere. I couldn't find any death records. All of the newspaper articles that were about, oh, he was in this sleigh accident.

All of these, they had like, here's how much his house cost, here's how much his horse cost, here's how much his second horse cost, and here's when that horse died.

No one would tell me how old this guy was because I got the impression that a lot of these reporters were just getting their information from people on the street.

There wasn't that sort of slavish devotion to like, here are the absolute facts that we have today. It was very different.

Now, you brought up Bill Tweed, I'm glad you did, because Bill Tweed was sort of tangentially involved in this incident in 1869.

He wasn't one of the men trying to manipulate the market, but he did sort of come into the story sort of more towards the end, as I understand it.

Is this what first brought him into your line of sight as someone of note that you wanted to learn more about?

Actually, yes, this was my first real introduction to Tweed. I knew he existed. I knew he's a very famous man, but I didn't really have a sense of who he was until I got to meet him through Fisk and Goad.

He became a patron, actually, of Jay Gold and Jim Fisk during the time that they were getting ready to corner the gold market. He became their friend.

Fisk and Goad were the upstarts picking fights with people like Cornelius Vanderbilt and the other very establishment Wall Street characters who were also very ruthless people, especially when it comes to money.

But Tweed became their patron in their various battles. And just before the gold quarter, Golan and Fisk brought Tweed onto the board of directors of the Erie Railroad, which was their power base on Wall Street.

So Tweed was very directly involved in the backroom discussions. As you say, he wasn't on the front lines of it until the end, when the issue ended up in the New York courts. And Tweed controlled the law in New York City by controlling the judges.

And so he managed to rescue Jay Golan and Jim Fisk when they were really deep in the big muddy by having one of his judges intervene on their behalf. But that was my first real introduction to Tweed and then what he was all about.

I'm curious, have you always been like a history buff? Did you take any history classes at college or is this something you just came into as more of a, as you explained before, it was just a way to tell this story?

Or were you always doing deep dives like this?

I was always interested in history. I took a few history courses in college, but I didn't start doing deep dives like this until first the gold ring.

And then after that experience, a few years later, I had the chance to write a book about James Garfield and then Tweed.

Working on Capitol Hill and working in government, you become very aware of history, of precedence to anything that's going on today.

I mean, to understand anything going on in Congress, for instance, you need to have some sense of history, how it fits into a flow of events. And that's been very helpful to me over the years.

13:04

Researching Boss Tweed

Okay, so Bill Tweed, your third book is about him, and it was published in 2005, I believe.

Yes, 2005.

Okay, so yeah, just like 21 years ago, happy birthday to the book.

Unlike your first book, which had sort of a key event as its anchor, this one, Boss Tweed, is about the sort of sprawling life and influence of this one person.

And I'm curious as a writer and a researcher, how did your process of research and writing differ between those two subjects?

Okay, that's an interesting question. Every one of my books, even my long biographies, tends to be of a slice of a person's life. I like the idea of building a story.

Every book, every story has a basic narrative arc. It starts at point A and point B. On the Tweed book, you'll notice that I make very short shrift of the first 40 years of his life.

I really introduced him when he's in his early 40s, during the Civil War. And what drew me to his story was very much how he, in the last decade or so of his life, he grasped power in a very big way and then lost it.

And that rise and fall was something that fascinated me, how someone could reach that pinnacle and then lose it. Also with writing a book like this, you're very much driven by the materials you have, by the research.

And I was very lucky to find a couple of things that opened conceptual doors to me.

When I started doing some actual serious digging into Boss Tweed and what he was about, one of the first things I came across was a congressional committee report on the election of 1868.

1868 is probably the most crooked election held in our country's history. And in New York City, it was the year that Tweed consolidated power.

That year, I think the numbers were something like out of about 150,000 votes cast in New York, about a third of them, 50,000, were either fake or fraudulent or repeat voters or made up. And the level of fraud was astounding.

There were people voting literally 10 or 20 times with the help of the local sheriff's office. They naturalized something like 40,000 citizens right before election day so that they could vote on election day.

So that year, the frauds were so flagrant that Congress appointed an investigating committee. They went to New York and they took testimony for several weeks.

And the result was a transcript about 600 pages long of interviews, testimony, sworn testimony from dozens and dozens and dozens of people, from Tweed and Samuel Tilden at one end to the actual repeat voters.

And some guy off the street who was asked to vote 20 times, and he would describe how he went about it, how he registered in 20 different places, and how he was read all at around by the sheriffs.

The people who were selling fake naturalization papers to get a few extra people in the door. Now, all these people were testified, and I had their stories and their voices in my hand.

That was the first piece that kind of fell out of heaven for me as a writer. At first, I thought of maybe making the entire book just about election day that year. And then I found a couple of other things.

I found Tweed's testimony to the Committee of Aldermen after he had been arrested, after he had escaped to Spain, after they dragged him all the ways back from Spain.

He had made an agreement with the prosecutors that if he gave a full confession, they might be open to releasing him. At that point, he was older and in bad health, so that he could die at home.

So he gave a full confession in his own voice, in his own words, to the Committee of Aldermen. And that now exists. It's about a five or six hundred page transcript that I had in my hand.

The prosecutors, of course, broke the deal. Tweed died in prison after he produced on his side of the bargain. And one other thing on sources, because this is how you shape a book based on what you have.

I came across Samuel Tilden, of course, who plays the role in this story. He is the lawyer who steps in after the New York Times exposes the secret account books of the Tweed ring. Tilden is brought in to try to figure out how to bring a legal case.

In his papers at the New York Public Library, there are two or three boxes of all of the bank material he got on Tweed that he used to figure out the cash flow of the Tweed ring.

It includes hundreds of canceled checks, hundreds of deposit swaps, dozens of these handwritten spreadsheets showing bank account balances moving from one bank account to another to another.

Holding Boss Tweed's personal check in your hand is a very cool experience.

Yeah, I can only imagine.

It's in pen. These are physical objects. It's not online.

When you look at them, you can see this check is for, this is paying the grocer, this is paying the doctor, this is paying a bribe to the city alderman, this is paying a payoff to Jim Fisk, this is for furniture, this is for my wife's doctor, this is

another bribe. It just makes it very human. And from that, I was able to get a good grasp of, and one of the overhanging questions of this whole story is, to what extent was Tweed actually guilty?

And how guilty were the other people, the other Tweed-ridden members, who did not spend time in jail? So those are probably the three things that shaped the book.

The Boss Tweed All right, you're listening to American Criminal. We're here talking with Ken Ackerman, author of Boss Tweed. We are talking about William Tweed and the Tweed Ring.

I'm glad you talked about, you know, finding those kinds of sources and being able to hold them in your hand, because I was going to ask you about, you know, choosing your sources for your work, because you're typically writing about subjects that,

you know, are from like 100 plus years ago. So it's not like you can go out and interview people who lived through it typically. And so, you know, in that case, you are sort of limited with your sources.

But I guess it is sort of going in and finding these historical documents that sort of leads you through the process.

Yeah, it's a very interesting thing. When you write about someone who lived that long ago and was controversial, you're better off not talking to people, in a sense. I find this even more so with the book I wrote after this was about J.

Edgar Hoover, the head of the FBI, almost anyone alive who knows him or knew him. And there are plenty of people who knew him, either hates him or feels, has a bias one way or the other. And those biases cover what they tell you.

With someone like Boss Tweed, who was vilified so heavily, both during his lifetime and after he died, secondary sources are just heavily unreliable. The only thing that you could really trust were contemporary first-hand accounts.

And particularly, sworn testimony, is there people have to tell the truth, or at least we hope they have to tell the truth, or else documents. So it means more digging, but it makes it more interesting.

Because when you look at things from the contemporary point of view, it's often very different from the legend that's created later.

You know, every now and then we'll get... People are able to comment on our episodes on Spotify, and every now and then people will sort of ask us a question about something.

They'll say, oh, why didn't you write about this part of this person's life? Or, you know, you didn't cover this crime when you're talking about this person.

And more often than not, it's because this is a rumor that has been started, and there's no actual, you know, evidence to back these things up. Or people will conflate two different criminals because they were around the same time.

And so I think what you're saying is a really important lesson, people, because we just, you hear something, especially with how much stuff is out there on the internet, you can sometimes just hear something or read it written down, and you just kind

of assume that it's true. So a lot of my research, as you know, I'm reading a lot of books, I'm watching a lot of documentaries, I'm reading a lot of newspaper articles, and I'm then having to sort of sift through all of my notes and all of the

information I have, and trying to figure out like, where is the truth in all of this? And often, you know, we'll have a source from a criminal themselves.

And I will every now and then need to remind myself, but we'll also want to remind our listeners that, you know, this is what this person has said, and they are the only account of this story that we have.

So keep that in mind because they're telling their version as they remember it, or as how they wanted to be remembered. And that's not always the same as what actually happened.

With Tweed, he suffers under an even worse situation in that what people mostly remember about Tweed are the Thomas Mast cartoons. Because the Thomas Mast cartoons, for one thing, they are so good as cartoons. I mean, the drawings are so effective.

But they are propaganda. They are trying to make Tweed look ludicrous, greedy, fat, arrogant. And that's the way the cartoons are drawn.

And most people, when they think of Tweed, they think of the cartoons. Even shortly after he died, more people had seen the Thomas Mast cartoons of him than they had ever seen actual photographs of him, or ever seen him as a living person.

People are kind of surprised when you tell them that for most of the time he was in power, Tweed was very, very popular. The New York Times had started attacking him almost a year before they actually got their hands on the evidence.

And during that time, people didn't believe it. They didn't want to believe it. They felt they had a good deal.

Now, yes, there was corruption in New York City, but there's always been corruption in New York City. So, yes, living in a big city means there are pickpockets in the alley and the streets are dirty, but so it goes.

But Tweed kept taxes low for wealthy people. He kept property values rising for wealthy people. For poor people, he provided jobs and services that others did not.

And so when the truth came out about the crimes, and I don't want to sugarcoat this, the crimes were real. His amount of spilling and fixing and election fixing is mind-boggling. The crimes were real.

But people viewed him, in many cases, as a source for good. The way he empowered the working class, he brought the immigrants into the political mainstream.

The way he built the city was new sidewalks and Central Park, the Brooklyn Bridge, other things. So there are a lot of clashing images with Tweed. The easy way to put it is, but for the stealing, he would have been a great man.

But the stealing is what defines him.

Yeah, it's something that we mention at the very end of our episode four is, what could he have been if he hadn't corrupted his own career? Like, he was clearly a very good politician. He was great with people.

He was great at remembering names. He was great at negotiating and making deals and offering this person this or get this from the other guy.

And it makes you wonder, like, he could have joined the pantheon of, like, the great American politicians, but he chose to go a different way instead.

And so he is remembered in a lot of people's minds as this Thomas Nast, like, archetypal political boss.

And it's something that I wrestled with a lot in writing about him, especially towards the late chapters, the late part of his story, when he is brought down, when he was very much a subject of prosecutorial abuse.

And when you talked to lawyers and explained to him how he was treated, the fact that he was jailed over civil suits, the fact that he was convicted of 204 counts of fraud, but they were misdemeanor fraud.

The fact that of all the Tweed ring major players, he was the only one who was successfully prosecuted. All of those things. My feeling is that you have to view the person as a package.

If he had been an honest man in that sense, he probably would not have been as good a politician. The way the world worked back then, it was a very edgy time. Politics was a very corrupt field.

At the time Tweed was stealing his money, there were plenty of people in Washington, DC involved in scandals of their own. The whiskey ring, the credit mobile, yay, and it's a long list of the grant era scandals.

One historian calls it the age of good stealings.

It started right during the Civil War, the amount of graft of cheating the government, selling the government shoddy, rusty arms, rotten clothing, rotten food for exorbitant prices, price gouging against the government during the Civil War when the

country was enthroned, was embattled, is kind of shocking. But that's the atmosphere, the environment that Tweed learned his craft in. And he was better at it than other people, for good and for bad.

Again, that's something that we took care to mention in our episodes was that he didn't invent this idea, but he definitely was one of the men who perfected it, who really turned it into a craft.

Okay, while we're still on the subject of Bill Tweed, is there a chapter of Bill's life that you find especially interesting?

Or if we're going to put it another way, if you're at a dinner party and Bill Tweed comes up, what's the story that you go, oh, you want to know about Bill Tweed? Let me tell you about this one time or this one part of his life.

There are certain things that people just don't know about him and assume about him. And we talked about the prosecutorial abuse and the fact that Tammany Hall actually did a lot of good for people.

I guess the one thing I would mention is that people don't know about is his role in the Civil War. In trying to write about someone like Tweed who lived in this period of the Gilded Age, most Americans, we are not good with history.

The level of ignorance about so many things is very high. But people who do know history, they generally know about two or three things. They have a pretty good understanding of the Civil War and know it pretty well.

They know World War II pretty well. They're generally aware of Franklin Roosevelt and the New Deal.

But that vast set of, what, 80 years between the Civil War and Franklin Roosevelt, and maybe Theodore Roosevelt, they have some sense of in the early 20th century. But a lot of the rest is a blur.

For instance, the lack of knowledge about World War I in America is kind of shocking, really. And especially that the line of presidents after Lincoln, between Lincoln and Roosevelt is very much forgotten.

So to talk about Tweed, I thought it was very important to place him in the Civil War. Because people understand if you could say, if you could tell where someone was in the war. Were they on the Union side?

Were they on the Confederate side? Were they serving the Army? Were they pro-slavery?

Were they anti-slavery, pro-secession, anti-secession? It tells a lot about them and it helps the reader understand who they were. So with Tweed, Tweed actually, even though he never got near the front, he played an important role in the Civil War.

He had to deal with the New York Draft Riots, which happened on his doorstep, just as he had become the chairman of the Democratic Party in New York, the chairman of Tammany Hall's General Committee.

It involved his voters and the Irish Catholic voters who were the base of Tammany Hall. But it was at a time when he had steered Tammany to support the war.

He was a pro-war Democrat in a city crawling with copperheads, anti-war Democrats, and immigrants who didn't understand why they had a stake in fighting, and who felt that the draft laws were extremely unfair, which, objectively, they were.

In the draft laws during the Civil War, you could, a wealthy person could pay $300 and get out of survey, while a poor person would have to give their life on the battlefield. And so the draft riots in New York erupted in the middle of 1863.

And at the time, the governor of New York, Horatio Seymour, a long forgotten name, was, he was very much a copperhead against the war, against Lincoln. He was in charge of handling it, and he failed miserably.

At the end of the riots, during the riots, it was Tweed and his circle, who were out on the streets, who were visible, trying to keep things calm, keep things under control as best they could.

And after the draft riots, it was Tweed, along with a Republican named Orson Blunt, who worked out a deal with the Lincoln administration to keep the draft functioning in New York while finding a way to satisfy poor people who got stuck in the

middle. And it's really what put Tweed on the map and made him very, very popular over the next 10 years, both among wealthy New Yorkers and poor New Yorkers. And it's something that people don't know about him at all.

By the time he becomes extremely corrupt, you know, it's four or five years after the war.

And we're back with Ken Ackerman, author of Boss Tweed. We're talking about William Boss Tweed and the Tweed ring of the 1870s. Yeah, the draft riot is such a fascinating part of his life.

It was a complex story to tell. You know, we have a limited amount of time in our episodes to tell these stories. And it was such a complex thing.

So I'm glad you brought it up here, because we did cover it.

But I don't think it can be overstated, like how important that event was in shaping the trajectory of his career and his popularity in New York, which, as you said, there was a lot of conflicting and complicated dynamics going on about supporting

the war, because at a state level, New York was on the side of the Union. But a lot of people within New York did not support the war, because there were a lot of immigrants who just didn't understand what was going on and why they were being asked

to go and fight. And a lot of people who did business with Southern states and Southern businesses or who had family in the South. And so it was a very, very complicated period.

So it's something that if people are interested in it, I think you should look into it because it's fascinating and very complex.

33:31

Orange Riot Aftermath

I think it was about eight years after the draft riot. So Bill Tweed is very, very popular, but he's about to start the downturn is when we see the orange riot happen. And that's like a lot smaller than the draft riot.

And it was something that we just didn't have room for when we were sort of, you know, we were trying to explain to everyone, like here's how, you know, he was brought down and here's what was going on.

But I'd love to talk about the orange riot with you, because it felt to me like another moment that's quite important in Bill's story. Would you mind giving us like a quick rundown of what the orange riot was?

This is one of those forgotten moments in New York City history, but it was in a way is kind of a subconscious scar on the psychology of the city because it was a very violent event and very large event.

New York in that period, the mid-1800s had a number of riots. It had outbursts of violence that were quite striking. There was several in the 1850s, and then the draft riots during the Civil War, and then this one.

The actual immediate cause was there was something called Orange Day, which is the anniversary of the Battle of the Bourne from 1690, which was a battle in Ireland, between basically between Protestant and Catholic.

The battle was won by the Protestants. It was William of Orange who was fighting James II for any vicious tree buffs in the group.

But it was a dividing line between the tensions between Northern Ireland and the rest of Ireland that have persisted over centuries. That dividing was established at the Battle of the Bourne, and the Protestants won that battle.

So every year for the last 300 years, or today it would be 400 years, in Northern Ireland among Protestant Irishmen, on that day they have a celebration. And in New York, they had an annual parade.

For the Catholic Irishmen, who were the large majority of the Irish population of New York, they found this parade a terrible insult. The religious hatreds and tensions were very intense on both sides.

The Catholic side vastly outnumbered the Protestant side on the island of Manhattan. So every year, the Protestant Irishmen would have a march.

Every year, there would be riots, and bricks would be thrown, and a few people would end up at the hospital. And every year, the violence would get a little worse and a little worse and a little worse.

Finally, in 1871, and the reason the date's important, because as you say, this was after the New York Times and Thomas Nast had been attacking Tweed for about a year, but they had no evidence, so they were very ineffective.

And Tweed remained mostly popular in the city. But the city was on edge. There had been a couple of labor strikes that year.

It was going on at the same time as the Paris Commune across the ocean, and people would have parallels.

When they were getting ready to have their march, the Catholic Irish were threatening massive violence, and the city leaders were unsure what to do. So Oakey Hall was Tweed's mayor, a mayor of New York City under the Tweed regime.

He refused to give them a parade permit. And so what this happened, the Protestant side cried foul, free speech. We have a right to have our parade too.

So Tweed, excuse me, Hall was at the last minute overturned by the governor, John Hoffman, who was another Tammany Hall creature, overruled the mayor. And so at the last minute, they decided to have the parade.

The parade consisted of about 150 actual Protestant Irishmen participating. And thousands of police. The police, national guard, all called out to surround the small number of actual marchers.

And one of the police, one of the national guard's troops that day was Thomas Nast, just to put him in context. So they marched down, it was 8th Avenue.

When they got to around 20th Street, they ran into a solid wall of Catholic Irish, both out in the streets and in all the buildings surrounding them, just raining rocks down on the police and the marchers.

Raining rocks, throwing garbage out the windows, taunting them. And at one point, somebody, no one really knows who, but somebody, and you have thousands of armed people in a tense situation like that, somebody pulled the trigger, a shot rang out.

When once the shooting started, the National Guards and Police, they suddenly had to defend themselves. So several volleys rang out.

And by the time about 20 minutes was done, there were between 35 and 105 people dead, and dozens more injured lying on the ground that day. It was a very bloody day.

It's hard to make sense of the injury reports, as by some, it was as many people were killed that day as in the New York Draft Riots a decade earlier. But most of the reports were around 30 to 40 dead.

In the aftermath, both sides were furious about it. The Irish Catholics felt that Tammany Hall had betrayed them, that they had mismanaged the whole situation because of all the confusing on again, off again management.

The Protestants declared it as a victory over the rabble. And so the level of tensions suddenly just rose very high. And the anger against Tammany Hall on the machine rose very high very quickly.

It was in that environment, literally about a week after the riot, that the New York Times got its hands on the secret accounts of the Tweet ring.

You know, what became the scoop of the century, the actual evidence, and started running it on their front page, in their famous secret accounts disclosures. And so that was the environment that it was dropped in, right after this orange day riot.

And as you say, it's something that's largely forgotten, even in the histories of Boss Tweed. It's not mentioned that often. But it's right there in the public record.

You know, when we were talking before about how important chronology is, this is what happened in the week before the disclosures.

Yes, I'm very glad that we found time to discuss it here, because it was something that was just, it was gonna take so much effort to sort of stop the episode and be like, okay, now we're gonna explain this one thing.

But it is really an important thing, because, you know, in my head, I'm reading this, and then, you know, you read about how these reports are then coming, like these attacks are starting in earnest, and then you get the evidence come out, you know,

about a week later. And so you have these attacks that are just coming one after another of like, you know, people from their base blaming Tammany and Tweed for what's gone on. But then you also have evidence of this corruption.

And so I was wondering, and, you know, feel free to speculate with me if you want, do you think that the Tweed ring might have withstood the Times' exposé of their corruption had they not also had to withstand the battering they took over the Orange

Riot? Riot?

41:17

Ringʼs Final Days

That's an interesting question.

I don't know that the Orange Riot itself is what tipped the balance, but it's easy to make the case that the Tweed ring could have withstood the New York Times exposure. Because even after the New York Times exposure, they were still legally immune.

The New York Times exposure showed that somebody had stolen a lot of money from the government. But at that point, there was still nothing that connected the theft directly to any particular person.

And to bring a criminal indictment, you need to show that somebody committed a crime. Here you knew that somebody did it, but you didn't know who. Also, Tweed still controlled the legal establishment.

He controlled the judges. He controlled the police. There were a couple of things that happened that kind of showed the Tweed ring losing its nerve during these couple of days.

For one thing, one of its judges, Judge George Barnard, one of Tweed's tools on the bench, was threatened by the reformers. And he issued an injunction on freezing city finances, which started the ring on its downfall.

Second, once the disclosures came out and people found out that all this money had been stolen, it created a panic among the bankers.

One of the things people don't realize with the Tweed ring is that the thefts were not thefts of New York City money.

Tweed financed his regime by borrowing, by issuing bonds and stock through Wall Street, sold by, bought by investors, yes, a lot in New York, but everywhere around the country and in Europe.

New York City bonds sold on the Berlin Stock Exchange and the London Stock Exchange. So when the disclosures came out, the bankers were suddenly afraid that New York City would default and they would be holding the bag.

And so that was what prompted New York's respectable elite to finally get together and realize they had a problem to bring Samuel Tilden into the mix to try to figure out how to legally overthrow them.

And then finally, Connolly, Richard Connolly, who is a controller, a key player in the ring, because as a controller, he controlled the actual bank accounts of the city and county of New York.

You can't do theft, you can't do corruption without Connolly controlling the money. And at one point, Samuel Tilden, representing the reform movement, put a lot of pressure on Connolly. There was a lot of finger pointing within the ring.

They did not hold together very well. And Connolly at one point turned tail and went to Tilden and made a deal. In exchange for what he thought would be immunity, which he never got, he gave them the ring, the keys to the controller's office.

He gave Tilden control of the controller's office, which gave Tilden suddenly access to all the books. Not just the stolen secret accounts, but to all the books. And that was what Tilden used to be able to make a case.

So if Connolly hadn't turned chicken, put it that way. If Barnard hadn't turned chicken, to put it that way. And the Tweed had held together, potentially they could have weathered this.

Not that that would have been a good thing for the world.

No, no, exactly, no. It's just, it's interesting to think about, you know, these decisions and the way that history can look very different just based on the way people decide in any given moment.

There's one final thing that I wanted to go over with that we didn't have time to cover in our episodes, but that was fascinating to me, was the way the Tweed ring tried to strike back at the New York Times, you know, in our episodes, we mentioned

when they tried to bribe the publisher of the Times right before the evidence was about to be published, and there was also the attempt to bribe Thomas Nast, which didn't, there wasn't anyone specifically from the ring that was like directly involved

Oh yeah, the pressure on the New York Times and Harper's Weekly by Tweed and his group was intense.

There was physical intimidation. They had detectives follow Lewis Jennings and the Times reporters down the street. He was arrested a number of times.

It was very conceivable that you could throw someone in jail back then for some trumped up charge of defamation, civil action and have them thrown in jail. They tried that several times.

The Harper and Company, the corporation, Harper Brothers Corporation that put out Harper's Weekly and employed Nass. They were the largest corporation in New York at the time. They employed 500 people.

They were the largest publisher in the country. One of their biggest customers was the city of New York, to whom they sold textbooks. And at one point, the ring cut off Harper Brothers Company from selling textbooks to the city.

A major financial blow to the company. At one point, the Harper Brothers thought about firing Thomas Nass, because they were in such a hole. Three of the Harper Brothers, they had a meeting, the four Harper Brothers, three of them wanted to fire him.

Fletcher Harper, who was the publisher of Harper's Weekly, he basically said of Nass goes, then I go. And he stood up to his brothers and kept Nass on the fold. On the New York Times, they did a number of things.

They tried to throw them out of their building, over on some question about their ownership of the New York Times building. And they tried to take over the stock.

It was not an unusual thing, especially with Jay Gould and Jim Fisk and the games they were playing on Wall Street, that if you managed to get just one or two shares of a company's stock, you could go in front of a judge, especially if it's a judge

that's been bribed. And again, this was not uncommon back then. And have the company put in receivership and get your own favorite person named as receiver. They threatened several times to do that to the New York Times.

It's kind of reminiscent to what's going on right now.

I don't want to get into modern politics, but there were a couple of shares of New York Times stock that were owned by people who it was feared might be open to sharing them with members of the Tweedry.

Shortly before the final secret accounts were published, the Times managed to buy the last 30 shares of publicly owned stock in their own company in order to avoid the company being bought out.

There was a very real scare because if Tweed wanted to buy out the Times, he had the combined fortunes of Jay Gold and Jim Fisk and the Erie Railroad and City Hall behind him.

I mean, if it was a fight of who had the most money in the banking cap, Tweed would win. But Times managed to control the last couple of public stockholders to sell their stock in order to protect the company.

It was very bicey, the kind of pressure that was put on both of those companies.

Yeah, because they were really the only ones at first who were sort of pointing out this corruption, and all the other newspapers were shouting them down.

And sort of the other newspapers were saying that, you know, Harper's and the New York Times were the corrupt ones. And then slowly the other newspapers all sort of fell in line once they sort of realized that the Tweed ring was going down.

It's worth mentioning that at the time, one of the ways that the Tweed ring controlled the newspapers was through advertising.

And several million dollars per year, and million dollars in 1870s equals, you know, tens or hundreds of millions of dollars today. Basically, buying off newspapers.

If you were friendly to them, then they would pay millions of dollars to advertising your pages. It's a kind of bribery. They cut off the New York Times and Harper's Weekly, but several other newspapers subsisted on payouts from the city government.

So a couple of times in our chat today, you've mentioned, you know, your experience in, you know, the American political system and you briefly eluded to it a few minutes ago, just sort of with the idea of modern American politics.

And I'm curious to know, you know, when you're telling these stories from America's past, what kinds of patterns or echoes have you noticed in how things play out, either like in society at large or in the political system?

50:15

Corruptionʼs Enduring Relevance

Well, you know, it's a funny thing.

The Tweed book came out, I wrote it about 20 years ago. It's been out there for that time. Over the past 20 years, I've frequently had the chance to give talks about Boss Tweed.

And there's almost never a time when political corruption isn't on the front pages in some way, shape or form. He's always relevant.

One can argue that the situation today, again, I don't want to get too political, that the level of corruption today is reminiscent of the Tweed era. But he's almost always been relevant.

These questions of what constitutes corruption, how much of an infection on the body politic is it, how dangerous is it, have always been there.

The oddity about Tweed, that the question he poses of us is stealing is bad, even when it's done by someone who's a nice person. And Tweed is an attractive character to write about because his personality is such a contradiction.

In his personal dealings with other politicians and people he would beat, he would often have to make promises and commitments. And he had a very strong reputation for honesty, for personal honesty.

If he gave you his word, he would do something for you, you could count on it. And this coming from the most prolific municipal thief in American history, it's very stark, but it shows the vagaries of human nature.

He is a very human character with strengths and weaknesses and a lot of shades of gray.

Ken, I've so enjoyed talking to you about this. I could chat with you for hours and hours about Boss Tweed because it's such a fascinating, complex story. I feel like we've barely scratched the surface, but I'm going to leave it here.

And before we say goodbye, I want to ask you, do you have another project that you're working on, like another book or an article we should keep an eye out for? I know before you said that Boss Tweed is being republished this year. Is that right?

Yes, four of the books that I wrote 20 years ago, Boss Tweed, Young J.

Edgar Hoover, Dark Horse, my book about the Garfield assassination and the Gold Ring, are all going to be republished by a new publisher in the next couple of months. It's my way of taking these old books and giving them a place for posterity.

So they will all be coming out with a new publisher. And I'll have an announcement hopefully about that soon.

Great, excellent. Well, we'll make sure to leave a link to your website in our show notes, so everyone can go and visit your website and keep an eye out on those things. But Ken, it's been such a delight talking to you.

Thank you so much for taking the time to chat with us here at American Criminal. We really appreciate it.

It was really fun. Thanks for having me.

That was our producer, Joe Callan's conversation with Kenneth Ackerman, author of Boss Tweed, The Rise and Fall of the Corrupt Paul Who Conceived the Soul of Modern New York. It's available in print, e-book and audio wherever you buy books.

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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.