1. Humble origins

William Tweed was born on the Lower Eastside of Manhattan in 1823 to a Scottish-Irish family. He came from humble enough origins, as his family hacked it out as furniture makers, and hoped that William would become the fourth generation to run the family business.

Wikimedia Commons

He left school at age 11 with every intention of doing just that but decided it wasn’t for him. Instead, he reentered school and studied accounting, which would prove very valuable in the future when he started siphoning money out of the New York City Treasury and into his pocket.

2. Engine No. 6

The life of an accountant was not in William Tweed’s future, and his rise to power actually came when he joined a volunteer fire company. Fire companies back in the 1850s did not resemble the ones comprised of trained, brave individuals that we have today, and acted as much like a gang as they did as firefighters.

Wikimedia Commons

Eventually, Tweed helped form Americus Engine Company No. 6 and adopted a fierce Bengal tiger as its logo. Tweed soon maneuvered his way into a position as a foreman and then used strong-arm tactics to make sure Engine No. 6 was the first to any fire in Manhattan.

3. Tammany Hall

It was at Engine No. 6 where Tweed developed his prowess in obtaining power using any means necessary. After a while, his efforts landed him in hot water and an alliance against him tried to ban him for life. But Tweed formed his own alliance and bribed the right officials to reduce his penalty to a three-month suspension.

Wikimedia Commons

Not only did Tweed successfully escape expulsion, but he rose to the position of Foreman of Engine No. 6. His ability to navigate himself to the top caught the attention of the major political party that ran New York City. He was a perfect fit for the Tammany Hall Democrats.

4. The Irish

Tammany Hall wasn’t all bad… at first. Many underrepresented immigrants fresh off the boat were protected by Tammany Hall at a time when they were exploited and struggled to get a foothold on the shores of the United States.

Wikimedia Commons

Men who were in a position to keep these subjugated people under their thumb were coveted by Tammany Hall, and William Tweed was one of those men. Irish people, in particular, benefited from Tammany Hall protection, but it always came at a price, and the cost was counted in votes.

5. National politics

At the age of 28, Tammany Hall encouraged Tweed to run for alderman. In 1852 he won the election. That same year, he won another election to the US House of Representatives. But his zeal for national politics was less than spectacular, and he lost his seat after his first two-year term.

Getty Images

Tweed didn’t have a flair for national politics, but that realization made him even better at the local level. He was appointed to the New York County Board of Supervisors in 1856, and by 1860 he was at the head of the Democrat General Committee.

6. “Boss” Tweed

Within months of obtaining the top position for New York Democrats, he was also sitting atop the Tammany Hall General Committee. This is when Tweed really stepped up his corruption game. He paid Judge George Barnard to certify him as a lawyer, and he opened an office where he charged for “legal services” when in reality companies were paying him for his influence.

Thomas Nast Cartoons

Instead of being a criminal lawyer, he was a criminal who was a lawyer. It took him three years to maneuver his way to the top of Tammany Hall, and when he did so, he became “Grand Sachem.” People started calling him “Boss.” He even adopted the Engine No. 6 tiger as Tammany Hall’s new logo.

7. New York City Draft Riot of 1863

Irishmen who were arriving by the tens of thousands in the early 1860s faced an impossible choice: pay $300, or sign up for the Union Army and die on the battlefields of the Civil War. In July of 1863, New York City was undefended by Union troops (they were busy mopping up at Gettysburg) and full-fledged riot took hold of the city that killed 119 people.

Thomas Nast Cartoons

During the riot, “Boss” Tweed took advantage of the situation. He actually warned the rival Republican Mayor of the impending violence and got him out of the city. This put him in the perfect position to curry favor, which he did by accepting bribes to keep men from being conscripted in the army.

8. “Our Boss”

Boss Tweed was rising fast in New York City and not everyone was thrilled about it. Republicans were especially perturbed about losing their hold on the city during a time when they dominated Northern politics. But Boss Tweed was a very effective leader, and there wasn’t much he was unwilling to do to get his way.

Photo by Universal History Archive/Universal Images Group via Getty Images

Tweed never really put too much effort into hiding what he was doing. He rubbed shoulders with the city’s elite, and if he couldn’t pay someone off, he’d just strong-arm them until they capitulated. But someone was unafraid to take shots at him and used a very unusual medium to attack the Boss.

9. Thomas Nast

Thomas Nast would rise to fame in the late 1860s when his innovative, satirical comics led directly to the arrest of Boss Tweed. Nast was a German immigrant who came to the United States with his family when he was six years old. Just like Tweed, school wasn’t for him, and he dropped out at an early age.


School wasn’t for Nast because he spent all of his time drawing and doodling when he was supposed to be doing his homework. He made it just two years longer in school than Tweed, but unlike Tweed, when he returned to school in he found his calling at the National Academy of Art.

10. “Recruiting sergeant”

Soon after he joined the Academy, he had to drop out because his parents couldn’t afford the tuition. So, in 1855, at just 15 years old, Nast got a job as an illustrator for Leslie’s Illustrated Newspaper. Seven years later he was hired by Harper’s Weekly, and that’s where he made his name.

Photo by © CORBIS/Corbis via Getty Images

Originally, Nast became famous for his depictions of the Civil War. He believed in the fight taking place down South and depicted images that encouraged men to join the Union Army. In fact, President Abraham Lincoln described Nast as the “best recruiting sergeant” in the country.

11. Shakespeare and the President

Nast got nasty when it came to politics, and after the Civil War, he wasn’t pulling any punches. His attack on President Andrew Johnson and his handling of the Reconstruction era is legendary. The cartoon he created depicts Johnson as the evil Iago as he plots against Othello.

The wounded veteran (portrayed as the Moor Othello) is being denied his rights after fighting for his country. The Shakespearean scene portrayed and all the other images depicting past promises by Johnson reveal a President with a flawed plan who doesn’t care about anyone. Johnson was later impeached and escaped indictment by one single vote.

12. The “Tweed Ring”

Nast wasn’t afraid to take shots at anyone, and soon Boss Tweed landed in his cross-hairs. The “Tweed Ring” ran New York City and there was no end to their corruption. They bribed city officials, rigged elections, and corrupted the judiciary.

Wikimedia Commons

A prime example of the kind of corruption conducted by the Tweed Ring was the election of the Recorder of New York City. Always one to return favors, Tweed put his support behind Judge Barnard; the same judge that illegally issued his law license.

13. Under his thumb

Tweed made a point of dipping every one of his dirty fingers and toes into all the little pools in New York City. He served as a New York State Senator, Director of the Erie Railroad, and the Deputy Street Commissioner of New York City, among other posts.

He also had his hands in private companies such as being the Director of the Tenth National Bank, proprietor of the Metropolitan Hotel, and he bought the Printing Company and Manufacturing Stationer’s Company, which he made the city’s official printer, and stationary printer, respectively.

14. The Treasury

One thing that Tweed was notorious for was overcharging, and when it came to his printer and stationery companies, he charged exorbitant fees. But there was a bigger prize he had in mind, and it came in the form of the city treasury. He cleverly obtained the prize of New York City Treasury by creating an audit board that oversaw it, then sat on the audit board.

Photo by © CORBIS/Corbis via Getty Images

Taking over control of the Treasury is when Tweed got really out of control. He set up fake leases and pocketed the funds. He also set up unnecessary repairs and bought overpriced goods using treasury funds, then effectively pocketed the extra and laundered into his coffers.

15. The Dead Rabbits

New York City was beginning to take notice; Tweed and his cronies had their share of enemies. To combat them when they wouldn’t accept a bribe or cooperate, the Tweed Ring used the largest Irish immigrant crime gang in New York City: The Dead Rabbits.

Getty Images

The Dead Rabbits were the Irish answer to being a minority group in a city that didn’t want them. Violence was their best means of keeping other gangs at bay, and in 1857 they caused the Dead Rabbits riot that resulted in eight men killed and dozens injured.

16. Senator Jailbird

Nast wasn’t the only one taking on Tweed and the corruption that surrounded him, but — at first — the efforts were mostly ineffective. For example, one week before Tweed ran for New York State Senator in 1871, the New York Times published a damning account of his corrupt practices and it was sufficient enough to have him arrested.

Wikimedia Commons

The sheriff, a man by the name of Matthew Brennan, didn’t keep Tweed in jail long. A $1 million bond paid to the sheriff saw to Tweed’s release. Just days later, he defeated his opponent and won the State Senate seat anyway.

17. “Them damned pictures!”

After the State Senate election, there was no hiding from the press. Nast worked for an editorial magazine, but he never held back when it came to expressing his opinions. In later years, he was nicknamed “The President Maker” for swaying the results of six presidential elections.

Nast wasn’t pulling any punches when it came to Tweed, and his cartoons portrayed him in the worst of ways. After the State Senate election and the subsequent cartoons that came with it, Tweed was said to have commented, “My constituents don’t know how to read, but they can’t help seeing them damned pictures!”

18. Yachts and mansions

Boss Tweed didn’t try very hard to hide his fortune and flaunted it like a model in a bikini contest. He was the third-largest landowner in New York City and owned a mansion on Fifth Avenue and 43rd Street. It had a horse stable close by and he also had a Greenwich estate and two private yachts.

Wikimedia Commons

From their position as auditors of the city treasury, the Tweed Ring used the funds like their own private piggy bank. But the books were cooked by the former accountant and reports vary widely about how much he stole. Estimates are between $30 million to $200 million, or $365 million to $2.4 billion in today’s dollars.

19. Diamond stickpin

Boss Tweed was living the good life at the expense of the city and those he placed under his thumb. He didn’t smoke and barely drank, but he always had fine cigars and whiskey for his friends. His waistline was evidence of his love of food, as he often dined on the best: oysters, tenderloin, and duck.

One accessory he wore that stood out the most was his 10 ½ carat diamond stickpin that he placed on the front of his shirt. It was outlandish for a public official to be indulging in such decadence, and Tweed did so unapologetically.

20. “Some years to come”

Nast and other journalists were taking shots at Tweed, but he remained standing. One journalist suggested as a spoof that a statue be erected of him. His friends thought that was a good idea and put the plans to work.

Perhaps sensing that he was attracting too much attention, it was actually Tweed who put an end to this idea after he commented, “Statues are not erected to living men … I claim to be a live man, and hope (Divine Providence permitting) to survive in all my vigor, politically and physically, for some years to come.”

21. A corpse called “New York”

Boss Tweed would survive “some years to come” but his days were certainly numbered. Nasty Nast was heating up, and taking down Tweed became something of a crusade. He did arguably his best work attacking Tweed, and it was starting to have an effect.

After Tweed’s release from prison and subsequent election as a state senator, Nast produced a particularly damning cartoon. He depicted Tweed and New York City Mayor A. Oakley Hall (among others) as vultures eyeing a corpse that was named “New York.”

22. $500,000 and a new life

The negative press was freely flowing across the city and Tweed was getting alarmed. So he did what a corrupt politician always does when someone won’t stop raking muck at them: he offered Nast a bribe.

If Nast had a price that would make him stop drawing Tweed, he never received it. Tweed had an agent meet with Nast and he offered him $500,000 to stop his cartoon attacks and move to Europe. Even though it was 100 times his annual salary, Nast refused, and the drawings kept coming.

23. Samuel J. Tilden

Tammany Hall was just too powerful to take on from the outside. They were involved in the judicial system from top to bottom, from street cops to judges. The press was powerful, but they couldn’t take them down.

The man who ended up answering the call to take down Tammany Hall was actually a New York Democrat. Lawyer Samuel J. Tilden had a good relationship with Tammany Hall until the constant attacks by the press made it impossible for them to hide their corruption.

24. Flying the coop

In 1873 the moment finally came when Boss Tweed was prosecuted and convicted. His crimes included larceny and forgery and the conviction came with a two-year prison sentence. He did the time, and when he was released, he was arrested again for not being able to pay the $6.3 million fine he owed for his crimes.

Prison life didn’t suit Tweed, even though he was allowed home visits while serving time. Before long, he used his home visits as a cover to skip town. In 1875 he escaped from prison and fled the continent for Europe.

25. A Spanish ship

Tweed was on the run and all the money that he stole over the years did not come with him. First, he went to Cuba, and then spent two years working as a seaman on a Spanish ship, living as a laborer and laying low.

Even though Tammany Hall retained its place as the leader of the Democrat party, the men that comprised the Tammany Ring were systematically prosecuted and convicted. Tilden’s efforts to take them down made him enormously popular and in 1874, he was elected Governor of New York.

26. Taken down by a cartoon

Meanwhile, Tweed was still on the run, and the United States government hadn’t forgotten about him. Neither had anyone else for that matter, as he may be the only man in history to be taken down by a cartoon.

While working his unassuming job and doing his best to keep a low profile, someone spotted him on a Spanish dock and recognized him from Nast’s cartoons. He was subsequently arrested and extradited to the United States where he faced prosecution again. Nast: 2; Tweed: 0.

27. No escape

Tweed landed back in prison in 1877 and was desperate to get out. He actually managed to make a deal with the New York Attorney General where he would reveal all of his crimes over the years in exchange for his release.

Tweed made good on his promise and delivered a report of all the crimes he could remember committing. The only problem was the state reneged on the deal. Rivals in Tilden’s governor office still hated Tweed, and were happy to let him rot in prison.

28. $2,500

William Tweed did not “survive in all [his] vigor, politically and physically, for some years to come,” as he would be dead the next year. He contracted a severe case of pneumonia that led to his death. Reports say that at the time of his death, his net worth was valued at $2,500.

The New York City Mayor refused to fly the City Hall Flag at half-staff, but Tweed still did have some friends. His funeral was kept quiet by his family, but a large crowd still came to the family’s residence. The Times even wrote that perhaps his punishment was “harder than he deserved.”

29. Elephants and Donkeys

Thomas Nast continued to draw his satirical cartoons and etched more than a few lasting images into the American psyche. Not only did he sway presidential elections, but you can thank him for creating the Republican elephant and popularizing the Democrat donkey.

Nast left Harper’s in 1886 and received a job in President Theodore Roosevelt’s Administration. Roosevelt had been a big fan of Nast’s work, and was happy to appoint him as the Consul General to Guayaquil, Ecuador in 1902. Unfortunately, the appointment turned out to be a death sentence. Nast contracted yellow fever and died just five months into his new job.

30. Nast’s legacy

Nast’s legacy lives on in various ways as the political cartoons and political satire have a huge presence in American society. The “Thomas Nast Prize” and the “Thomas Nast Award” are given every year to the best editorial cartoon and the best cartoon on international affairs, respectively.

Library of Congress

Nowadays, we have Saturday Night Live and the Daily Show (among many others) that satirize the current political climate. Taking a comedic approach to politics causes us to howl with laughter, and cringe when it feels real. Nast was so successful with his cartoons that he managed to take down a powerful political machine and forever engraved political satire as a highly expressive and influential means of sharing ideas.