A Brief History of Gangsters


By Brian J. Robb

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In this fascinating Brief History, Robb explores the history of the greatest crime bosses from around the world and their effect on pop-culture.



Part One: American Gangsters before Prohibition

Chapter 1Lawlessness in the Old West

Chapter 2Organized Crime before Prohibition

Chapter 3The Five Points Gangs

Part Two: Prohibition and After: Rise of the American Gangster

Chapter 4‘Lucky’ Luciano: The Man Who Organized Crime

Chapter 5Murder, Inc.: Lansky, Siegel and the Mob Assassins

Chapter 6Get Capone! – The Life and Times of ‘Scarface’

Chapter 7Public Enemies: The John Dillinger Gang

Chapter 8Bonnie and Clyde – Dustbowl Desperadoes

Chapter 9Mickey Cohen’s Hollywood Takeover

Chapter 10The Mob in Hollywood

Chapter 11The Mob and the President

Part Three: The Post-War American Mob

Chapter 12Prime Minister of the Underworld

Chapter 13Capo di tutti Capi: Inside the American Mafia

Chapter 14The Changing Face of American Gangsters

Part Four: Gangsters Worldwide

Chapter 15United Kingdom: The Krays

Chapter 16European Gangsters: Jacques Mesrine

Chapter 17Central European Gangsters: The Serbians

Chapter 18Russia: From the Soviet Union to the Oligarchs

Chapter 19Latin America: The Colombian Drug Lords

Chapter 20Asia: The Triads and Yakuza

Chapter 21Australia: Ned Kelly

Part Five: Film and Television Gangsters

Chapter 22Gangsters on Screen






Gangsters. The word conjures up a world of crime, gun molls, and corrupt political power. It also suggests a certain amount of glamour: the fedora hats, trench coats, the ‘rat-a-tat-tat’ of Tommy guns, the nightclubs and speakeasies, the gambling dens and the dames in flowing gowns. That image comes more from the thrilling gangster movies of the 1930s than the actual gangsters themselves, although some of them did live up to it.

The modern use of the term ‘gangster’ originated in an Ohio newspaper of 1896 and simply referred to a group of people involved in organized crime. It seems to have had a maritime origin, going back to the seventeenth century – according to the Oxford English Dictionary. Famous gangsters range from Italian-Americans like Lucky Luciano, Meyer Lansky and Bugsy Siegel to those found around the world, such as Britain’s notorious Kray Twins, France’s Jacques Mesrine, and the Triads and Yakuza gangs of the Far East.

Gangsters – especially the romanticized American gangster of Prohibition and the Depression era, a time when America’s rulers failed their people – have proved to be resilient and attractive figures, somehow glamorous in their law-breaking lifestyles. They have transcended the time and place of their origins and have become archetypal figures, a repository of ordinary people’s dreams about the romance of crime.

With a strong focus on the American archetype, A Brief History of Gangsters explores the histories, both personal and criminal, of key figures in the worlds of organized crime. The book closes with a study of the gangster in popular culture, particularly in film and television. As recent hit TV series such as The Sopranos and Boardwalk Empire and blockbuster movies like Public Enemies (2009) and Gangster Squad (2013) show, the gangster is here to stay.

Although the infamous figure of the American gangster is largely associated with the period of the 1920s to the 1940s – roughly from Prohibition through to the Second World War – there are deeper roots. In an American context, the rise of the gangster – that is, someone who is part of or who runs an organized crime network – really begins in the Old West.

During the 1800s the notoriety of the proto-gangster ‘outlaw’ figure was spread through the rise of newspapers that, often gleefully, chronicled their misdeeds. Members of organized gangs of outlaws, such as the James Gang; the group led by Billy the Kid known as ‘the Rustlers’; the Doolin–Dalton Gang; and the ‘Wild Bunch’, all became public figures.

The untamed wilderness of the Western half of the United States attracted a certain type of rugged, self-reliant settler, while the lack of law (initially, at least) made the West a particularly attractive place for those of a criminal bent, many of whom were fleeing the authorities in the East. The spread westwards by settlers who first arrived on the continent of North America in the East developed from the early seventeenth century and ran through until the early twentieth century. The American frontier – the ‘Old West’ or ‘Wild West’ – described this expansion westwards, largely in the second half of the nineteenth century.

General lawlessness was common, with personal crimes slowly giving way to organized criminal activity carried out by groups of people (usually, but not exclusively, men). Commonplace crimes included horse stealing, highway robbery, and currency counterfeiting. Pioneer families were often targeted for their goods and supplies, as the relatively few lawmen struggled to cope. Stagecoaches would most often escape attack if they carried armed guards, but small criminal gangs – often comprising no more than two or three people – could easily target relatively unprotected homesteaders. Due to the nature of these crimes, with many seen as being against the struggles of the expanding nation itself, punishments were often extreme.

Centres of the cattle business, such as Dodge City, and mining towns, like Tombstone, Arizona, became attractive to the increasingly organized crime gangs of the Old West. Cowboys resting up in large towns would spend the money generated from months on the cattle trail, so were frequent targets for bandits, as were miners, who dealt in silver and gold, and the wealth those minerals created. Key events of Western legend, such as the 1881 gunfight at the O.K. Corral, were examples of the lawlessness of the time. Although often seen as bandits themselves, the three Earp brothers – Virgil, Morgan and Wyatt – were in fact investors in a local mine and local law officers when they killed a trio of outlaws during the confrontation.

Separated from family or community, the (mostly) young men who strived to find new lives on the American frontier often found themselves in areas where law enforcement was difficult to maintain or next to non-existent. Some of the key members of outlaw gangs had experienced the violence of the Civil War in the 1860s, while others who attacked banks, stagecoaches and trains had fallen upon difficult times having failed to make a success in the cattle industry or in other fields after the war. Some were simply individualists, those for whom organized society held no attraction, and who were determined to go their own way in life (perhaps a basic trait of the American frontiersman), even if that meant falling foul of the law.

Often the only opposition to such activity came not in the form of legally designated lawmen and their deputies, but in the shape of informally organized community ‘posses’, where armed men set out to pursue or dissuade the bandits from their local activities. In California in the mid-nineteenth century, criminal activities flourished. Infamous outlaw gangs were responsible for much of the crime that terrorized the frontier, and it is in these groups that the roots of America’s later gangsterism is to be found.

Jesse James and the Western Gangs

Perhaps the most notorious American outlaw of the Old West was Jesse James, whose exploits became the stuff of legend and myth within his own lifetime, thanks to newspaper coverage and dime novels embellishing his story. Born in Missouri in September 1847, Jesse Woodson James was the son of a man who was both a Baptist minister and the founder of a college. His father died of cholera in 1850, when Jesse was only three years old. He had an older brother, Alexander Franklin – known simply as Frank – and a younger sister, Susan. His mother eventually remarried (for the second time) to a doctor in 1855 – they had four further children together.

Growing up prior to the Civil War in the north/south ‘border’ state of Missouri, where Jesse’s family were originally farmers and slave owners, he experienced some of the growing anti-slavery movement’s activities that sometimes led to outbreaks of violence. The resulting Civil War, which came about largely due to the South’s resistance to the North’s desire to outlaw slavery, did much to shape the rest of Jesse James’ criminal life.

Aligned with the Confederate side, representing the Southern States, the James family witnessed some of the battles between Unionist militia known as ‘jayhawkers’ and secessionist guerrilla fighters dubbed ‘bushwhackers’. Frank James joined a local secessionist military group, resulting in a revenge attack on the James farm in May 1863 by Unionists, during which Jesse’s mother and stepfather were tortured. This served to radicalize Jesse, who joined his brother as part of ‘Bloody’ Bill Anderson’s Confederate raiders (several members of that group would go on to become members of the James Gang).

Jesse saw much action during the civil conflict, and learned about weapons and warfare on the job. He and his brother were participants in several notorious actions, including the Centralia Massacre of September 1864, in which many unarmed Union troops were killed or injured. As a result of the brothers’ activities, the James family were driven out of Clay County in Missouri and had to move south into Nebraska.

Shot (for the second time) while intending to surrender to a Union patrol near Lexington, Jesse James was – according to legend – left for dead, only to rise again as an outlaw. As he was presumed dead, he was never granted an amnesty at the end of the conflict in 1865. In the chaos that followed, Jesse was able to disappear, embarking upon his criminal exploits around 1866.

It wasn’t until 1869 that Jesse James, along with his brother Frank, were identified as wanted men following a bank robbery in Gallatin, Missouri. As with most criminals of their type, public opinion was solidly against them and their activities, with the community keen to see the pair of outlaws brought to justice. However, Jesse was smart enough to begin using the media that vilified him and his brother to try to change public opinion. He wrote an ‘open letter’ to the Liberty Tribune newspaper, published on 24 June 1870, asserting the James brothers’ innocence and claiming instead that they were the victims of political persecution following their wartime service for the Confederacy.

There followed a decade of propaganda, on behalf of and against Jesse James, while the criminal activities of his gang continued. A sympathetic newspaper editor, John Newman Edwards, did much to create an unearned Robin Hood image for Jesse James, portraying the proto-gangster as an avenger who struck wealthy railroad bosses and venal bankers on behalf of the common folk, although he kept the resulting loot for himself and his gang members.

Jesse James had set about creating his own myth as a ‘good guy’ outlaw. During one train robbery, the James gang distributed copies of an account of the event then underway to passengers to pass onto the media in the aftermath. The main concerns of this pre-written ‘history’ were to exaggerate the height of the gang members to point out that the hands of the passengers were studied so the gang would avoid robbing ‘working folk’.

Jesse cultivated a cult of the personality, making his marriage to Zerelda Mimms in April 1874 a matter of public interest through the pages of the St. Louis Dispatch newspaper – now this modern Robin Hood had found his Maid Marian. Further sympathy for Jesse was generated when Pinkerton Agency detectives, charged with his capture, raided the James’ family home in January 1875. A device intended for illumination was thrown into the house through the window, but it exploded, killing Jesse’s nine-year-old half-brother. This, and other incidents, were built up to depict Jesse and his outlaw gang as righteous folk, fallen on hard times as a result of the political situation following the Civil War, suffering persecution. The gang became famous, robbing stagecoaches, trains and banks, often in front of large crowds of witnesses: the gang members even took to ‘performing’ theatrically for the gathering public crowds during their daring ‘daylight robberies’.

The politicization of crime would be a hallmark of later gangster organizations, of which Jesse James was a pioneer. Pleading for a pardon for his actions, Jesse succeeded in setting the Democrats and Republicans, and their respective ‘tame’ press organizations, against one another over his fate. However, the bank raid in Northfield, Minnesota (subject of the 1972 Philip Kaufman movie The Great Northfield Minnesota Raid), in September 1876 turned the tide against the James Gang. Three of the gang members were killed and the Younger brothers, James Gang associates, were wounded and apprehended. Following a concentrated manhunt, of the whole gang only Frank and Jesse remained at large.

While Frank adopted a new identity and attempted to ‘go straight’, the restless Jesse continued his criminal activities, and in 1879 recruited a new gang, many of whom were aware of their leader’s fame as an outlaw, and who were not ‘battle-hardened’ in the way Frank and Jesse had been by the Civil War. The new James gang returned to train hold-ups. The robberies became more violent, and these more undisciplined gang members frequently turned on one another, making Jesse paranoid that one of his own gang might kill him.

That’s exactly what happened in April 1882 (as seen in the 2007 movie The Assassination of Jesse James by the Coward Robert Ford), when James gang member Robert Ford shot the thirty-four-year-old Jesse in the back of the head, while he was hanging a picture on the wall in their remote hideaway. Jesse’s body was identified through his two previous chest wounds and the missing tip of his middle finger. Instead of gaining the reward he thought was his, Ford was charged with murder, although later pardoned. Along with his brother Charley, Ford then toured the country putting on a vaudeville show in which they re-enacted the killing of Jesse James in front of paying crowds.

Such was the notoriety and legend of Jesse James, many refused to believe he was really dead. The New York Daily Graphic had declared Jesse James to be ‘the most renowned murderer and robber of his age’, so it was unlikely his folk legend would fade quickly. Several later criminal figures claimed they were actually Jesse James, or used his name to justify their crimes in the wake of his death. Even as late as 1951, the 101-year-old J. Frank Dalton claimed that he was in fact Jesse James, having survived the assassination attempt of 1882. The body buried in 1882 was exhumed in 1995 and DNA testing proved it was indeed the corpse of notorious outlaw and proto-gangster, Jesse James.

In a similar style to Jesse James, Billy the Kid – born in November 1859 as William Henry McCarty Jr, also known as William Bonney – was a veteran of war who turned to crime. Billy’s war was the Lincoln County War of 1878, after which he became an outlaw on the American frontier, surrounded by myth.

Billy grew up in a mining encampment called Silver City in New Mexico, only turning to crime after his mother’s death in 1874. He first became a horse thief, then – aged just seventeen – killed for the first time when he ran into a bully who’d been tormenting him. The Lincoln County War suited Billy as a time and place where he could become lost, and as a way of learning the use of weapons and the consequences of violence. Various shoot-outs, assassinations and targeted killings followed.

After the war, Billy was briefly a cattle rustler. After a failed attempt to win an amnesty, he was captured by Sheriff Pat Garrett (who’d also participated in the Lincoln County conflict) following a gunfight in 1880. Found guilty of murder for his part in the gang slaying of Sheriff William J. Brady, Billy avoided the noose in April 1881 when he killed two of Garrett’s deputies who were guarding him, and escaped. He would be free from the law for three months, hidden by Hispanic sheep herders. However, Garrett was on the Kid’s trail, tracking him to Fort Sumner, where in the summer of 1881 he shot him dead at the age of just twenty-one.

Billy the Kid’s criminal career was short-lived, but his fame spread far and wide across the United States. The 1881 price on his head – a $500 bounty – issued by the Governor of New Mexico, helped make him notorious, although exaggerated accounts of his feats helped. The Kid’s youth and quickness on the draw were built up, especially in the kind of dime novels he’d grown up reading, and so another proto-gangster legend was born. Public opinion turned against Garrett, seeing his killing of ‘the Kid’ as an unfair act. During his short-lived crime spree, Billy the Kid was said to have killed between fifteen and twenty-six men – the legend prefers the total of twenty-one, one for each year of the Kid’s life. As with Jesse James, others claimed to be Billy the Kid after his death; DNA testing of his remains was thwarted by court proceedings in 2004, with the state of New Mexico preferring to protect Billy the Kid’s legacy as a tourist draw over verifying the facts.

The equally youthful Sam Bass ran a criminal gang in the 1870s and robbed the Union Pacific Railroad gold train from San Francisco in September 1877, taking $60,000, still the largest ever robbery from that still-existing railroad service. The Bass Gang staged various robberies, most often netting less than $500 each time, before they moved up to more risky stagecoach robberies and then railroad trains. Holding up four trains within twenty-five miles of Dallas brought the Bass Gang to the attention of Pinkerton agents, who were teamed with a special company of Texas Rangers to track them down.

By threatening his ill father, the Rangers were able to turn a member of the gang, Jim Murphy, into an informer. While an ambush of Sam Bass’s next planned raid was being prepared by the Rangers, Bass shot and killed a local sheriff who’d noticed him while he was scouting the Williamson County Bank. Attempting to escape, Bass was mortally wounded by a pair of vigilant Texas Rangers. Sam Bass died the following day – his twenty-seventh birthday.

The pattern was repeated in the tales surrounding other such proto-gangsters of the Old West, including the Dalton Gang, Black Bart, and Butch Cassidy and the ‘Wild Bunch’. During a two year period from 1890, the Dalton Gang – comprising three Dalton brothers and five others – specialized in train and bank robberies. The three Dalton brothers – Gratton, Bob and Emmett – started out as lawmen like the Earps, but turned to crime when they were not paid (a fourth brother, Bill, was part of the Wild Bunch). They recruited others into the gang, pulling their first job in a raid on a casino in Silver City, New Mexico. Thereafter the Dalton Gang held up passenger trains, stole horses and raided train stations to rob waiting passengers. Ambition got the better of Bob Dalton who decided he wanted to go one better than Jesse James and rob two banks in broad daylight at the same time.

Wearing fake beards, the gang attempted the double deed in Coffeyville, Kansas in October 1892. Despite the disguises, they were recognized by locals who quickly gathered together an armed posse while the gang were still in the banks; a frantic shoot-out ensued as they attempted a getaway. At least three townspeople and a marshal were killed, as were four members of the gang: two Dalton brothers – Gratton and the recognized leader, Bob – as well as Dick Broadwell and Bill Power. Of the five participants in the bank raids only Emmett Dalton survived, but he had been seriously wounded: reportedly, around twenty bullets were removed from him. He was tried and imprisoned in March 1893. Later, he would write books about his experiences as an outlaw in the Dalton Gang and enjoyed a career as an actor in Hollywood – in 1918, he played himself in a movie – before dying at the age of 66 in 1937.

Black Bart – born Charles Earl Bolles in Norfolk, England in 1829 – was an Old West outlaw who became known for the poetic messages he left behind after some of his raids. He robbed Wells Fargo stagecoaches around Northern California and Southern Oregon between the 1870s and 1880s. Although he only actually left poems behind after two raids, it became known as his trademark. Frightened of horses, Black Bart was a bandit who got around only by foot, never fired a gun during his raids, and was always polite, using good manners and no foul language, leading to him becoming known as a ‘gentleman bandit’. He controlled his victims by pretending to talk to his ‘gang’ hidden in nearby bushes, but he always operated alone.

Wounded during his final robbery, Black Bart made his escape, but dropped several personal items including a handkerchief. A laundry mark led Wells Fargo detectives to a cleaning company, where they got Bart’s address. Arrested and convicted, despite his protestations, Black Bart went to San Quentin prison for four years. Released in 1888 and in failing health, he went straight, apparently dying around 1917.

The charisma and notoriety of later gangsters can be seen in an earlier form in Butch Cassidy, the bank and train robber and leader of the ‘Wild Bunch’ gang. Robert Leroy Parker was born in 1866 in Utah and worked on several ranches, acquiring the nickname ‘Butch’. He took the surname Cassidy from his mentor, dairy farmer and cattle rustler Mike Cassidy (itself an alias). It wasn’t until 1889 that Butch Cassidy took up a life of crime full time, stealing $21,000 from a Telluride bank in co-operation with two other outlaws. Horse thieving and the operation of a protection racket – demanding money with menaces – followed, leading to an eighteen-month jail term.

Released from jail, Butch Cassidy involved himself even further in the criminal underworld, rising to become leader of a group of bandits known as the Wild Bunch. A spate of bank robberies followed, and in 1896 Harry Longabaugh joined the gang and became known as the ‘Sundance Kid’. Payroll thefts and stagecoach ambushes followed, with an ever growing manhunt making the gang’s criminal activities increasingly more difficult to conduct. After each raid the gang would split up and later reconvene at their ‘hole-in-the-wall’ hideaway, a secluded area in Dubois, Wyoming. In 1900 five members of the gang, including Butch and Sundance, cheekily posed for a studio group photograph, which they then mockingly mailed to the pursuing Pinkerton detectives. The lucrative raids continued, but the heat on the gang got too much, so Butch Cassidy and the Sundance Kid headed for South America, hiding out in Buenos Aires in Argentina.

Failing to change their ways after trying to run a legitimate ranch in Patagonia, the pair of outlaws continued to raid banks in South America, bringing them to the attention of Argentine law enforcement who in turn brought in the Pinkerton agents already on their trail. Fleeing their pursuers – and continuing to stage robberies on the way – Butch and Sundance ended up on the run in Chile. Although their deaths were never confirmed, in 1908 in Bolivia two unknown bandits were trapped in a house in San Vicente by members of the Bolivian army. Under siege, one bandit killed the other (who had been fatally wounded in the shoot-out with the army), before turning the gun on himself. The local police did not know the bandits identities, and they were buried locally in unmarked graves. Legend has it that these graves were the final resting places of Butch and Sundance.

Their story is also the story of the end of the Old West: in evading the ever reaching long arm of the law, they had to flee further than most, all the way to South America. The myths, legends and tales that surround these often flamboyant and theatrical figures were the reading matter of many of the men who went on to become the key names of the true era of the classic American gangster. Many were born in the final quarter of the ninteenth century, and they would define the criminality of the first half of the twentieth century. The mythologizing of the outlaws of the Old West would be carried on to the urban gangsters who replaced them.



The American gangster is largely an urban figure. The gangsters and their organized crime networks arose alongside the growth of American cities in the late-nineteenth and early-twentieth centuries. Just as the cities spread, grew, and their skyscrapers reached ever higher, so did the tentacles of organized crime spread, infecting the commerce and politics of the modern city and dominating the underworld. Most large American cities were infested with the disease of crime from their inception. It was the arrival of Prohibition – the nationwide ban on the manufacture, transportation and sale of alcohol between 1920 and 1933 – that led to a boom in gangsterism across and between the major US cities. The early history of organized crime in a trio of major American cities illustrates the trends.

New York

New York developed from Algonquian Native American lands settled by European colonists throughout the sixteenth and seventeenth centuries. Originally called New Amsterdam, New York was a British-controlled trading port in the early 1700s, and a centre of the slave trade. Following the American Revolutionary War, the city remained a British military and political base of power until the evacuation of 1783. By 1785 New York was the American national capital (before it settled in Washington D.C. in 1790), and in 1789 America’s first President, George Washington, was inaugurated in the city. Slavery was abolished there in 1827, although racial discrimination would continue for many decades.


On Sale
Jan 6, 2015
Page Count
288 pages
Running Press

Brian J. Robb

About the Author

Brian J. Robb is the New York Times and Sunday Times bestselling biographer of Leonardo DiCaprio, Johnny Depp, and Brad Pitt. He’s also written acclaimed pop-culture books on silent cinema, the films of Philip K. Dick, Wes Craven, and Laurel and Hardy, and the TV series Dr. Who and Star Trek. He is co-editor of the Sci-Fi Bulletin.

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