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Best Gangsters From the 1830s to the 1930s

I earned a Bachelor of Arts degree in political science in 1995. My interests include political and social issues and history.

They are businessmen, competitive and protect their own. They have their own little group that they are part of and identify with and fight other groups.

Americans, or maybe people generally, have a fascination with outlaws and gangsters. Even though gangsters are horrible, because they are violent and do destructive things, we still seem to like their colorful gangster names, their style and the fact that they just really don't care what we think.

Well, I think it runs deeper than that. We know something is seriously wrong in society and tend to appreciate those who appear to operate outside of it. Well, gangsters don't really operate outside of society, exactly. They're part of society. They do the same thing everybody else does, just illegally. They are businessmen who are competitive and protect their own. They have their own little group that they are part of and identify with and they consequently fight other groups.

Sounds like society to me!

But we like rebels. Here in America, all of our heroes are rebels, including George Washington and, to some, even George Wallace. Al Capone is another one.

So, I've compiled my own little biased list of my own favorite gangsters: And none of them were dirty rats that squeal to the coppers.

Bill The Butcher Poole

William Poole, or Bill The Butcher, was made famous by Martin Scorcese's epic film about old school gangsters, Gangs of New York. The main antagonist in the movie was modelled after Bill. However, Scorcese used a little poetic license, because Bill was around in the 1830s and 1840s (died in 1850s) and the film was set in the Civil War era of the 1860s. Nevertheless, as in real life, Bill made a colorful character for the movie.

In real life, Bill was an actual butcher (and he was in the movie too). And he liked knives. He also liked to pluck people's eyeballs out using his old school Rough and Tumble fighting style. He got his name in the New York Times because of this talent. He was the leader of the famous Bowery Boys. It should be noted he was also a fireman, known for their rivalries and gang fights against competing firemen, and this "vocation" led to him forming the Washington Street Gang.

He was also a racist and a xenophobe. He was part of the political organization the Know-Nothings, who didn't like immigrants; they were Nativists who wanted to keep America "pure". Therefore, Bill hated the Irish and his gang fights were often centered on battling such Irish New York gangs as the Dead Rabbits.

It should be noted too, that political and criminal lines were more than blurred back then. Criminal organizations openly supported and were supported by political organizations back then, doing dirty work at the polls and being enforcers. Tammany Hall, predecessors to the Democratic Party, had many alliances with gangs, for instance. So, Bill's nativist Know-Nothings was no exception. Politics and crime definitely did mingle. Is it different today? I guess that's a rhetorical question.

Bill The Butcher was racist, a xenophobe, brutally violent and greedy. But none of that makes him any less fascinating. He came from early America's unfortunate but very real gangster tradition that's carried on to this day. He's an historical figure in America and in gangland New York.

George Appo, Chinese-Irish professional pick-pocket and green goods scammer of 19th Century Five Points gangland: Before and after losing his eye from a gun shot.

George Appo, Chinese-Irish professional pick-pocket and green goods scammer of 19th Century Five Points gangland: Before and after losing his eye from a gun shot.

George Appo

George Appo was an expert pick-pocket and con man. He was half Chinese and half Irish, kind of on the opposite gangster spectrum from Bill the Butcher. He led a rough life, no doubt about that, proven by the fact that he only had one eye, having lost the other from a gun-shot wound brought about by a very disenchanted mark.

His father sentenced to prison for murder and his mother dead from drowning because a ship she was on sank, as a child George ended up in the hands of a poor family living in the lowest of the slums in New York known as Murderer's Alley. George quickly learned the tricks of his trade, picking pockets, being one of the best in the city. He lived by the code of the Good Fellow, never a rat and accepted the consequences of his crimes.

He eventually got into the Green Goods game, a con in which marks were promised counterfeit money but instead had their own loot stolen.

George Appo was not just some petty thief, he was a legend, a strange aberration even among gangsters, a biracial half Chinese and half Irish orphan that came up hard and received plenty hard knocks. He belongs on the list of the best of the mid and late 19th Century New York gangsters of the Five Points.

Tom Lee vs Mock Duck in the Tong Wars

The Chinese Tongs were social and business secret societies that were formed in the 1860s in the West to battle racist attacks and to consolidate business interests. By the late 1800s they were in full swing in New York Chinatown on Doyers Street where many Chinese had come in and set up shop.

By the early 1900s, Tom Lee was the Tong mob boss that pretty much ran New York Chinatown. He helped the politicians and the politicians supported him and his On Leong Tong too. He ran the gambling houses and opium dens without interference, until Mock Duck came into town and took over the On Leong's rival, the Hip Sing, and subsequently made an alliance with another gang known as The Four Brothers.

Mock Duck was a squat man who was brazen and always clad in chain-mail, like a typical Tong warrior, to protect himself against the hatchet-men. That term hatchet-man, by the way, comes from the Tongs. They literally used hatchets to mutilate their enemies.

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Mock Duck was known to put himself in the middle of a confrontation as an open target but to fire off so many rounds from his pistol that no one had a chance to shoot him.

He also had a penchant for gambling, in addition to wanting Tom Lee's gambling house revenue. When Tom Lee refused to give Mock Duck anything, Mock Duck went on a mission to topple Tom Lee and take over his gambling enterprises. He convinced the police to raid the On Leong gambling dens only then to take them over under the banner of the Hip Sing Tong.

Soon Mock Duck was prosperous in Chinatown, though he was forever having to contend with attempts on his life. In spite of a great many attempts by the On Leong to murder Mock Duck, he managed to survive and die much later after the Tong Wars, of natural causes.

Though he enjoyed a decent reign as Tong leader of the Hip Sing, his life was, of course, not without troubles. One of these troubles occurred when the Gerry Society decided to steal his adopted daughter away from him because she was white and because they didn't like Mock Duck's opium habit.

Strange story how Mock Duck ended up with a white daughter. Her name was Ha Oi, and she was the biological daughter of Lizzie Smith who had married a Chinese guy in San Francisco after her white husband died; she died and her Chinese husband married a Chinese woman; the Chinese guy died and his widow married Mock Duck who consequently ended up with Ha Oi. Then the Gerry Society took Ha Oi away from Mock Duck. I truly wonder what ever happened to that girl, she lived a crazy life in her early childhood, that's for sure.

Mock Duck, heart-broken, tried feverishly to get his daughter back, gave up and went on a gambling spree which is said to have made him rich and full of spunk again. Who knows? Could be.

The Tong Wars reached a height in the early 1900s, involving fights over women and even the murder of a popular stage performer at the Chinese theater at Doyers Street. There were many attempts to create peace by judges and even an intervention by both US and Chinese authorities. However, there always seemed to be a reason for hostilities to spark another Tong battle.

Eventually the Tongs settled more into legitimate community services for Chinatown; only to open the door to the Triads, Chinese secret societies with similar structure, code, blood oath and connections to the Tongs.

Doyers Street, home to New York's Chinatown, in 1898.

Doyers Street, home to New York's Chinatown, in 1898.

John Dillinger

John Dillinger was a depression-era hero. During those hard times, most people were much less likely to trust the bankers and the businessmen and they were more likely to trust a bank robber.

Dillinger's gang would go on bank robbing sprees, but Dillinger was careful never to let anyone get hurt. He was a gentleman. A gangster and a gentleman. Even when he kidnapped people for ransom, a common practice in his era, his supposed victims liked him; they said they had fun with the charismatic gangster.

I suppose he had style. He was mainly robbing the people's enemy and everyone knew it.

And I suppose he was a little too popular. And that's why Federal agents ambushed him while he was coming out of a movie theater. He'd been double-crossed by a supposed friend, an immigrant who was fearful of the authorities because she'd been in trouble for pandering. So, she squealed.

Dillinger was Everyman and the people looked up to him in an era when the little guy was getting squashed by the big guys. Dillinger was serving up some depression-era justice on the banks that were slapping farmers with foreclosures.

Another reason we love the outlaws.

The infamous Bonnie and Clyde.

The infamous Bonnie and Clyde.

Needless to say, Clyde escaped from prison. And he and Bonnie went on a crime spree, robbing banks and businesses across the Southwest.

Bonnie and Clyde

You gotta love a love story. Bonnie and Clyde were passionate for each other. And passionate for adventure.

And I guess opposites attract. Bonnie Parker was originally from a fairly well-off and stable family, she did well in school and was popular. But when her father died when she was a teenager, she ended up getting work as a waitress. And she was bored out of her mind.

Clyde Barrow came from a poor family. His father was a share-cropper. Clyde dropped out of school and started stealing cars and robbing stores. He met Bonnie when he visited an injured friend that she was taking care of.

When Clyde landed in prison, a rather rough and hellish prison, Bonnie came for a visit with a gun hidden in her bra for him.

Needless to say, Clyde escaped from prison. And he and Bonnie went on a crime spree, robbing banks and businesses across the Southwest.

In 1934, the police ambushed the duo as they were driving a stolen Ford through part of Louisiana, and riddled them with 50 bullets, basically mutilating the pair.

It's worth noting that, like Dillinger, people were more likely to protect this pair than turn them in. I suppose this is why they could only be caught by a brutal and sneaky ambush.

Paul Kelly Vs Monk Eastman

Paul Kelly and Monk Eastman were the remnants of the old school Five Points ghetto that was the birthplace of New York City's gangsterism. Paul Kelly's Five Points Gang christened the rising star Al Capone, otherwise known as Scarface. Al went on to make good in his own right, as a famous gangster of the 1930s.

But before superstar Al Capone rose to fame, there was Paul Kelly. A well-spoken and intelligent Italian who took on an Irish name because the Irish gangs were still notorious and popular in New York City during his time; which was the late 1800s and early 1900s. He was a boxer who used his winnings to open brothels and, in fact, had a monopoly of the bordellos in the Five Points. He was muscle for Tammany Hall and so had the protection of the politicians.

His chief rival, Monk Eastman, also had the protection of the politicians, though that protection would eventually be lost and given solely to Kelly.

Monk Eastman was a typical roughneck gangster who controlled the area east of the Bowery, while Kelly controlled the area west of it; the two fought for the neutral territory designated by Tammany Hall. Therefore Tammany Hall constantly had to call the leaders together to settle differences because the havoc of their gang-fights and gun battles made the citizens, and voters, nervous. Eventually it came down to Tammany Hall deciding the gangsters' differences should be settled with a boxing match. Though the fight was declared a draw, after the match Tammany Hall withdrew support of Eastman who then, consequently, ended up in prison.

With Eastman out of the way, Kelly ran New York but had to contend with internal rivals. He survived though and brought up some of the most famous of the gangsters in the early 20th century; men like Capone, Meyer Lansky, Bugsy Siegel and Lucky Luciano.

These men are important in gang history because they represent the decline of the Five Points as a focal point for gang activity and the end of such gangs as they were replaced with the much more sophisticated crime machine of the mafia. In this sense, though, they were a prelude to bigger things to come. Kelly became a labor racketeer which is an activity later taken over by the mafia. As stated, Kelly brought in the biggest of the gangsters of the 1930s, men like Capone, Meyer Lansky, Bugsy Siegel and Lucky Luciano. Their time was a turning point and pertinent to the timeline of gangland history. They laid the groundwork for dangerous and profitable times to come.

Gangsterism is popular, found in movies, in music, in video games and on clothing.

Gangsterism is popular, found in movies, in music, in video games and on clothing.

As I stated at the outset, gangsterism is as American as apple pie. OG from the 18th century, Samuel Mason, was one of our early gangsters and had also been a Captain during the American Revolution, a Justice of the Peace and a businessman. In addition to these endeavors, he was a prolific criminal. One of his famous exploits was his river piracy, in which he'd lure travelers off the Ohio and Mississippi Rivers with the promise of liquor at which point he and his gang would rob and kill their misfortunate visitors.

It should be noted liquor also played a big part in the formation and continuation of gangs; and not just during Prohibition. The famous Five Points district, the center of gang activity in the 19th century, was built up by green-grocery speakeasies where the gangs formed and collected. These "grocery stores" had rotten produce up front but the liquor in the back.

Everybody in America knows the game is survival. And we appreciate anyone who gets good at the game. Even if they lose in the end. We cheer the underdog and we cheer those who jeer authority. We know the odds are stacked and we look to those who beat the odds as examples of what we can do. We wonder what it'd be like to thumb our noses at everything and still do well. Our definition of gangster has changed over the years because at some point we realized it has more to do with an attitude than criminal enterprise.


Nathan Bernardo (author) from California, United States of America on July 23, 2014:

Thanks, Rachael. Good to know this piece is in search results, I hadn't checked it, though I do check if my articles show up in search results fairly often.

You're right, people champion the bad guys but still want the good guys to win.

Glad you found this piece educational.

Rachael O'Halloran from United States on July 23, 2014:

Whether they are watching a movie or reading a book, people seem to champion the bad guys while they are hoping the good guys win back the day.

Your article came up in my search results. I am researching several gangsters from the 1920s through 1940s. This was an interesting and enlightening article. Voted up, useful (at least to me!) and interesting.

Nathan Bernardo (author) from California, United States of America on March 28, 2014:

No problem, Treathyl. I appreciate your giving attention to my work and your contributions. Thanks for sharing my work in your networks too.

Treathyl FOX from Austin, Texas on March 28, 2014:

@NateB11 - Thanks for allowing my comments at your HUB. Extra thanks for actually taking the effort to say my real name. You went the second mile on that, Mr. Bernardo. :)

I shared this to my Pinterest board called BIO-Snapshots. When I pin something, it gets Tweeted and also shared to Facebook. Hope the circulation gets you more readers. Your HUBs are super interesting!

Nathan Bernardo (author) from California, United States of America on March 28, 2014:

I'm with you on that, SandCastles. I think George Appo's story is interesting for the same reason you do; he definitely had a rough life, with a lost eye to prove it, and was fighting the odds. You're correct some people straighten out their lives even when they've been in gangs, I know a couple people who've done it.

Treathyl, I'm glad I only write about this stuff and don't live it, then; because I don't want to get clobbered by a bat. I agree, organized crime is a horrific and brutal business, there's no doubt about that. I truly do not think there's anything good about a gangster lifestyle. And America is a great country, even with some of it's worst flaws.

SandCastles on March 28, 2014:

I've only heard about Bonnie and Clyde and Scarface. The only con that I find interesting is George Appo. It sounds like he turned to crime to simply survive like a character from Charles Dickens', 'Oliver Twist'. Some people who live that sort of life end up turning away from that lifestyle too like Paul.

Treathyl FOX from Austin, Texas on March 28, 2014:

So I was responding and my computer screen froze when I was about to publish the comment. So I will repeat and rewrite.

I used to work for the U.S. Customs Service which is a law enforcement agency that was on the front line of the war against drugs and other criminal-related enterprises. When I see or hear anything about gangsters, I feel like swinging a bat!! Although I resigned many moons ago from federal service, there were I learned “things about America” while being employed that I would rather not have known. All in all, God bless America.

Nathan Bernardo (author) from California, United States of America on March 28, 2014:

Your honesty is pure, Treathyl. I do realize it ended up being a long article, it's like a one-stop reference and overview of a hundred year span of highlighted gangsters. I find it fascinating and, yes, in the end, a tragic story. However, there are insights there into the fabric and psyche of America, for certain. Scorcese was brilliant in bringing that out in his movie on the subject.

Treathyl FOX from Austin, Texas on March 28, 2014:

(Yawn.) Boring.

Sorry. No matter whose story you tell, their tombstone reads the same. "Here lies Mr. or Ms. Reap What You Sow. What a useless existence. The world gained nothing by their presence. Everybody was sure glad they moved out of the neighborhood!"

Great HUB! The writing I mean. Me personally, I would written several HUBs, and made it a series.

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