Picture the gritty streets of old Boston, the rough-and-tumble saloons of the Wild West frontier, or the underground parlors of Prohibition-era New York. Back then, some Irish lads took a look at the rules of the land and decided they weren’t for them. And did they ever leave their mark – these men became infamous not just for their deeds but for how boldly they operated and the scope of their rackets.
Plagued by the struggles of immigrants but never lacking swagger, these Irishmen turned to lives of crime that were as thrilling as they were illegal. Names like Whitey Bulger, who had Boston on lockdown and a temper to match, or Billy the Kid, whose lightning-fast draw made him a West legend. But their stories mean more than just heists and murders – they show what life was like back then and what it’s like trying to get by when the game is rigged.
So get ready to step inside and meet the rebellious rogues who gave law enforcement the slip, creating notoriety that still sends shivers down spines. I’ll introduce the top ten Irish gangsters who raised the bar of crime to new levels.
These Are 10 Famous Irish Gangsters
- Billy the Kid (William McCarty)
- Ned Kelly
- James ‘Whitey’ Bulger
- Emmett Dalton
- James Freney
- John ‘Legs’ Diamond (Jack Moran)
- Owney ‘The Killer’ Madden
- Charles Dean O’Banion
- Michael Spillane (Mickey Spillane)
- Danny Greene
1. Billy the Kid (William McCarty)
| Full Name | William Henry McCarty Jr. |
|---|---|
| Aliases | Billy the Kid, Henry Antrim, William H. Bonney |
| Born | September 17, 1859 |
| Died | July 14, 1881 |
| Nationality | American (Irish descent) |
| Criminal Activities | Outlaw, Gunfighter |
Biography
Billy the Kid, born William Henry McCarty Jr., became one of the most infamous outlaws of the American Wild West. His story begins in New York City, where his Irish immigrant mother, Catherine McCarty, raised him and his brother in a harsh and unforgiving environment. After the death of his mother, young Billy moved west and began a life that would become legendary.
Early Life and Descent into Crime
Billy’s first brush with the law came at a young age. He was involved in petty thefts and quickly escalated to more serious crimes, such as horse theft. His early criminal activities set the stage for his later notoriety. As a teenager, Billy was known for his charm and agility, traits that helped him evade capture on multiple occasions.
Rise to Infamy
Billy the Kid’s reputation as a gunfighter was solidified during the Lincoln County War in New Mexico, a conflict that pitted rival factions against each other. Billy aligned himself with the Regulators, a group fighting against the corrupt influence of local businessmen and politicians. His role in this violent struggle included participating in several high-profile gunfights, which only added to his growing legend.
Capture and Escape
Despite numerous attempts by law enforcement to capture him, Billy the Kid’s luck seemed almost supernatural. He was arrested and jailed multiple times, but his daring escapes, including one where he famously killed two guards while escaping from the Lincoln County Courthouse, cemented his reputation as an elusive outlaw.
Death
Billy the Kid’s life of crime came to a sudden end when Sheriff Pat Garrett tracked him down to Fort Sumner, New Mexico. On July 14, 1881, Garrett shot and killed Billy, putting an end to the young outlaw’s short but notorious career.
Legacy
The legend of Billy the Kid has grown over the years, fueled by countless books, movies, and songs. He remains a symbol of the Wild West, embodying both the spirit of rebellion and the darker side of American history. His life and exploits continue to captivate audiences, making him one of the most enduring figures in the annals of crime and infamy.
2. Ned Kelly
| Full Name | Edward Kelly |
|---|---|
| Aliases | Ned Kelly |
| Born | December 1854 |
| Died | November 11, 1880 |
| Nationality | Australian (Irish descent) |
| Criminal Activities | Outlaw, Bushranger |
Biography
Ned Kelly, born Edward Kelly, is perhaps the most famous Australian outlaw, a bushranger whose exploits captured the imagination of a nation. Born in Victoria, Australia, to Irish parents, Kelly’s early life was marked by poverty and brushes with the law, setting the stage for his eventual turn to a life of crime.
Early Life and Family Struggles
Kelly’s father, John “Red” Kelly, was an Irish convict transported to Australia. The Kelly family faced significant hardships, including clashes with local law enforcement, which many believe were fueled by anti-Irish sentiment. Ned’s first run-in with the law came at age 14 when he was accused of assaulting a Chinese man. This was the beginning of a pattern of petty crimes that escalated over time.
Formation of the Kelly Gang
Ned Kelly, along with his brother Dan and friends Joe Byrne and Steve Hart, formed the Kelly Gang. Their criminal activities initially included cattle and horse theft, but they soon moved on to more serious crimes. In 1878, after a police officer was shot and wounded while trying to arrest Dan Kelly, the gang was declared outlaws. This event marked the beginning of a violent campaign against the authorities.
Key Events and Infamous Encounters
The Kelly Gang’s most infamous act was the robbery of the National Bank at Euroa and the Jerilderie raid in 1879. During these heists, they not only stole money but also took hostages, treating them surprisingly well. Ned Kelly’s charisma and the gang’s daring nature earned them a degree of public sympathy.
The Final Stand and Capture
The Kelly Gang’s final stand took place at Glenrowan in 1880. They planned to derail a train carrying police officers, but the plan failed. During the subsequent siege, Kelly donned homemade metal armor, which has since become iconic. Despite his armor, he was captured after being wounded in the legs. The other gang members were killed in the shootout.
Trial and Execution
Ned Kelly was tried and convicted of murder. His trial was a significant event, drawing considerable public attention. Despite petitions for clemency, Kelly was sentenced to death. On November 11, 1880, he was hanged at Melbourne Gaol, his final words reportedly being, “Such is life.”
3. James ‘Whitey’ Bulger
| Full Name | James Joseph Bulger Jr. |
|---|---|
| Aliases | Whitey Bulger |
| Born | September 3, 1929 |
| Died | October 30, 2018 |
| Nationality | American (Irish descent) |
| Criminal Activities | Mafia Boss, FBI Informant |
Biography
James ‘Whitey’ Bulger was a notorious figure in the American underworld, leading a double life as both a ruthless crime boss and an FBI informant. Born to Irish immigrant parents in Boston, Bulger’s early life set the stage for his future as one of the most feared and enigmatic figures in organized crime.
Early Life and Criminal Beginnings
Bulger grew up in the South Boston neighborhood known as “Southie,” a tough environment that shaped his early forays into crime. He was involved in various petty crimes as a teenager, which led to his first arrest at the age of 14. His criminal activities escalated quickly, and by the 1950s, he was heavily involved in armed robbery and truck hijacking.
Rise to Power
Bulger’s rise to power began in the 1970s when he became a prominent figure in the Winter Hill Gang, an Irish-American crime syndicate in Boston. Under his leadership, the gang expanded its operations to include drug trafficking, extortion, and loan sharking. Bulger was known for his brutal enforcement methods, including ordering the murders of anyone who threatened his operations.
FBI Informant
One of the most controversial aspects of Bulger’s career was his role as an FBI informant. Beginning in 1975, he provided information on rival criminal organizations, particularly the Italian-American Mafia, in exchange for protection from prosecution. This relationship with the FBI allowed Bulger to operate with impunity for years, as agents turned a blind eye to his criminal activities.
Fugitive Years
In 1994, tipped off about an impending indictment, Bulger went on the run, sparking one of the longest and most extensive manhunts in FBI history. For 16 years, he evaded capture, living under various aliases across the United States. His fugitive status only added to his legendary persona, making him a subject of widespread fascination and speculation.
Capture and Death
Bulger was finally captured in 2011 in Santa Monica, California, along with his longtime girlfriend Catherine Greig. His arrest ended years of mystery and led to a highly publicized trial in 2013, where he was convicted on multiple charges, including murder, racketeering, and money laundering. Bulger was sentenced to life in prison.
On October 30, 2018, Bulger was found dead in his cell at the United States Penitentiary, Hazelton in West Virginia. He had been violently beaten by fellow inmates, bringing a grim end to the life of one of America’s most infamous gangsters.
4. Emmett Dalton
| Full Name | Emmett Dalton |
|---|---|
| Born | May 3, 1871 |
| Died | July 13, 1937 |
| Nationality | American (Irish descent) |
| Criminal Activities | Train and Bank Robber |
Biography
Emmett Dalton, a member of the infamous Dalton Gang, was born into a family of outlaws who became notorious in the American Old West for their train and bank robberies. The Dalton family’s Irish heritage and the harsh conditions of their upbringing played significant roles in shaping Emmett’s path to infamy.
Early Life
Emmett Dalton was born in Belton, Missouri, as the youngest of the Dalton brothers. The family faced numerous hardships, and the Dalton boys were exposed to crime at an early age. Their transition from lawmen to outlaws was swift, driven by both personal grievances and the allure of quick wealth.
Formation of the Dalton Gang
The Dalton brothers, initially working as lawmen, grew disillusioned and turned to a life of crime. Emmett, along with his brothers Bob and Grat, formed the core of the Dalton Gang. They quickly gained notoriety for their audacious robberies, targeting trains and banks across Oklahoma and Kansas.
Criminal Exploits
The Dalton Gang’s most famous heist took place on October 5, 1892, in Coffeyville, Kansas. The gang attempted to rob two banks simultaneously, a feat of unprecedented boldness. However, the heist went disastrously wrong. The townspeople, recognizing the Daltons, armed themselves and confronted the gang. A fierce shootout ensued, resulting in the deaths of Bob and Grat Dalton, along with other gang members.
Survival and Capture
Emmett Dalton was the only surviving member of the gang from the Coffeyville raid. Despite being severely wounded with 23 gunshot wounds, he was captured and brought to trial. Emmett was sentenced to life imprisonment, but his story didn’t end there.
Post-Prison Life
Remarkably, Emmett was paroled after serving 14 years in prison. He emerged as a reformed man and sought to distance himself from his criminal past. Emmett moved to California, where he pursued various ventures, including real estate and acting. He even wrote a book, “When the Daltons Rode,” recounting his life and the gang’s exploits, which was later adapted into a film.
5. James Freney
| Full Name | James Freney |
|---|---|
| Born | 1719 |
| Died | 1788 |
| Nationality | Irish |
| Criminal Activities | Highwayman |
Biography
James Freney, often referred to as Ireland’s most famous highwayman, lived during the 18th century and became a legendary figure for his daring escapades and Robin Hood-like reputation. Born in 1719 in County Kilkenny, Freney’s life of crime was deeply influenced by the political and social unrest of the time, particularly the oppressive laws imposed on the Irish by the English.
Early Life and Motivations
Freney’s family was of minor gentry, but they faced significant hardships when their lands were confiscated by the English authorities. This loss of livelihood and status fueled Freney’s resentment and set him on a path of revenge against the English. His early years were marked by struggles, and he soon turned to a life of crime, seeing it as a means to retaliate against those who had wronged his family.
Highway Robbery
James Freney quickly became notorious for his skill and daring as a highwayman. He operated primarily in the southeastern region of Ireland, targeting wealthy English travelers and robbing them of their valuables. Freney’s knowledge of the local terrain and his ability to evade capture made him a formidable figure. He was known for his clever disguises and the strategic planning of his heists.
Public Perception and Folk Hero Status
Unlike many criminals of his time, Freney managed to garner a degree of public sympathy. He was often seen as a folk hero, with tales of his generosity towards the poor and his charismatic personality spreading far and wide. His exploits were romanticized in Irish folklore, and he was admired for his courage and audacity in challenging the English authorities.
Capture and Exile
Despite his numerous escapes, Freney was eventually captured. However, his notoriety and the public’s fascination with his exploits played a role in his relatively lenient treatment. Instead of facing execution, Freney was exiled. He fled to France and later returned to Ireland, where he lived out his final years peacefully.
6. John ‘Legs’ Diamond (Jack Moran)
| Full Name | Jack Moran |
|---|---|
| Aliases | John ‘Legs’ Diamond, Gentleman Jack |
| Born | July 10, 1897 |
| Died | December 18, 1931 |
| Nationality | American (Irish descent) |
| Criminal Activities | Bootlegger, Gangster |
Biography
John ‘Legs’ Diamond, born Jack Moran, was one of the most colorful and notorious figures of the Prohibition era. Known for his flamboyant lifestyle and numerous escapes from death, Diamond’s life was a testament to the violent and chaotic world of the 1920s and 1930s organized crime.
Early Life
Diamond was born into an Irish-American family in Philadelphia. His early life was marked by poverty, and he quickly turned to a life of crime to escape his circumstances. He earned the nickname “Legs” for his agility and ability to escape danger, traits that would serve him well in his criminal career.
Rise in the Underworld
Diamond moved to New York City, where he became involved in bootlegging during Prohibition. His operations spanned from New York to upstate areas like Albany. He was known for his ruthless tactics and willingness to engage in violent confrontations with rivals. Despite the danger, Diamond’s charm and charisma earned him the nickname “Gentleman Jack.”
The famous Black Hand Mafia was also very strong in New York at the same time.
Numerous Assassination Attempts
One of the most remarkable aspects of Diamond’s life was his ability to survive multiple assassination attempts. Rivals and law enforcement both targeted him, but he managed to escape death time and again. These escapes only added to his legendary status within the underworld.
Legal Troubles and Final Years
Diamond’s criminal activities inevitably led to numerous arrests and trials. However, he often managed to evade serious convictions due to a lack of evidence or legal technicalities. His luck began to run out in the early 1930s as law enforcement intensified efforts to dismantle organized crime networks.
Death
On December 18, 1931, Diamond’s luck finally ran out. He was shot and killed in an Albany rooming house, marking the end of his tumultuous career. The circumstances surrounding his death remain murky, with various theories suggesting involvement by rivals, disgruntled associates, or even law enforcement.
7. Owney ‘The Killer’ Madden
| Full Name | Owen Vincent Madden |
|---|---|
| Aliases | Owney ‘The Killer’ Madden |
| Born | December 18, 1891 |
| Died | April 24, 1965 |
| Nationality | American (Irish descent) |
| Criminal Activities | Bootlegger, Gangster, Boxing Promoter |
Biography
Owney ‘The Killer’ Madden, born Owen Vincent Madden, was a prominent figure in the underworld of early 20th-century America. Known for his ruthless demeanor and significant influence, Madden’s life story intertwines with the Prohibition era, organized crime, and the glitz of the New York City nightlife.
Early Life
Born in Leeds, England, to Irish parents, Madden emigrated to the United States as a child. The family settled in the Hell’s Kitchen neighborhood of New York City, a rough area that profoundly influenced Madden’s early life. By his teenage years, Madden had already established himself as a fearsome member of the Gopher Gang, notorious for their violent turf wars.
Rise to Power
Madden’s fearsome reputation earned him the nickname ‘The Killer’ after numerous street brawls and violent encounters. His criminal career took a significant turn during Prohibition, when he became heavily involved in bootlegging. Madden’s operations extended across New York, and he became one of the most influential figures in the city’s underworld. His involvement in the illegal alcohol trade brought him immense wealth and power.
Cotton Club and Nightlife
One of Madden’s most famous ventures was his ownership of the Cotton Club, a premier jazz club in Harlem. The club became a cultural icon, showcasing legendary performers like Duke Ellington and Louis Armstrong. While the club was a hotspot for the elite, it also served as a front for Madden’s various criminal activities, including gambling and prostitution.
Boxing Promotion
In addition to his bootlegging and nightclub operations, Madden became a significant figure in the boxing world. He promoted several prominent fighters and was involved in organizing major boxing matches. His influence in the sport further solidified his status as a key player in the New York crime scene.
Legal Troubles and Later Life
Despite his criminal empire, Madden faced numerous arrests and legal battles throughout his life. He served multiple prison sentences but managed to maintain his influence and operations. In the later years of his life, Madden retired to Hot Springs, Arkansas, where he ran a legitimate hotel business. He remained a respected figure in the community until his death in 1965.
8. Charles Dean O’Banion
| Full Name | Charles Dean O’Banion |
|---|---|
| Aliases | Dion O’Banion |
| Born | July 8, 1892 |
| Died | November 10, 1924 |
| Nationality | American (Irish descent) |
| Criminal Activities | Bootlegger, Gangster |
Biography
Charles Dean O’Banion, commonly known as Dion O’Banion, was a prominent figure in the violent and tumultuous world of Chicago’s organized crime during the Prohibition era. As the leader of the North Side Gang, O’Banion’s life was marked by his fierce rivalry with Al Capone and his involvement in the illegal alcohol trade.
Early Life
O’Banion was born to Irish immigrant parents in Maroa, Illinois. His family moved to Chicago when he was a child, settling in the tough neighborhood of Little Hell. O’Banion quickly became involved in crime, joining the Market Street Gang in his youth. This early exposure to criminal activities laid the foundation for his future as a gangster.
Rise to Power
O’Banion’s career in organized crime took off during Prohibition when he began running a bootlegging operation. He formed the North Side Gang, which became one of the most powerful criminal organizations in Chicago. O’Banion’s gang was involved in various illegal enterprises, including bootlegging, gambling, and robbery. His headquarters, Schofield’s flower shop, served as a front for his illicit activities.
Rivalry with Al Capone
One of the most significant aspects of O’Banion’s criminal career was his intense rivalry with Al Capone and the South Side Gang. The competition between the North and South Side gangs for control of Chicago’s bootlegging operations led to numerous violent confrontations. O’Banion’s boldness and willingness to challenge Capone made him a formidable adversary.
Notable Incidents
O’Banion’s audacity was evident in several high-profile incidents, including his orchestration of the Sieben Brewery raid, which significantly disrupted Capone’s operations. This move, however, escalated tensions and set the stage for a deadly showdown.
Assassination
On November 10, 1924, O’Banion was assassinated in his flower shop by gunmen from Capone’s gang. His murder marked a turning point in the Chicago gang wars, leading to increased violence and reprisals. The killing of O’Banion was a pivotal event that intensified the bloody conflict between rival gangs in Chicago.
9. Michael Spillane (Mickey Spillane)
| Full Name | Michael J. Spillane |
|---|---|
| Aliases | Mickey Spillane |
| Born | July 13, 1933 |
| Died | May 13, 1977 |
| Nationality | American (Irish descent) |
| Criminal Activities | Mobster |
Biography
Michael J. Spillane, known as Mickey Spillane, was a prominent Irish-American mobster from the Hell’s Kitchen neighborhood of New York City. He earned the nickname “The Last of the Gentleman Gangsters” for his style of conducting business with a blend of old-school respect and ruthless efficiency.
Early Life
Born in Hell’s Kitchen, a neighborhood infamous for its tough conditions and gang activity, Spillane quickly immersed himself in the local underworld. Unlike many of his contemporaries, Spillane managed to blend a veneer of respectability with his criminal undertakings, earning him a unique reputation in the New York crime scene.
Rise to Power
Spillane rose to power in the 1960s and 1970s, controlling the rackets in Hell’s Kitchen. His operations included loan sharking, bookmaking, and numbers running. Spillane was known for his ability to maintain order and avoid unnecessary violence, setting him apart from the more brutal tactics of other mobsters. His leadership style earned him respect both within his gang and among rival factions.
Conflict with the Westies
Spillane’s control over Hell’s Kitchen faced significant challenges from the Westies, a newer and more violent Irish-American gang. The Westies, led by Jimmy Coonan, sought to take over Spillane’s territory and operations. This conflict escalated into a violent gang war, marked by numerous confrontations and assassinations.
Assassination
On May 13, 1977, Spillane’s life was cut short when he was assassinated outside his apartment building in Queens. His murder was widely believed to be orchestrated by the Westies, specifically Jimmy Coonan, in their bid to seize control of Hell’s Kitchen.
Spillane’s death marked the end of an era and the beginning of a more violent chapter in the neighborhood’s history.
10. Danny Greene
| Full Name | Daniel John Patrick Greene |
|---|---|
| Aliases | Danny Greene |
| Born | November 14, 1933 |
| Died | October 6, 1977 |
| Nationality | American (Irish descent) |
| Criminal Activities | Mobster, Union Leader |
Biography
Danny Greene, known as “The Irishman,” was a notorious Irish-American mobster who became a major figure in Cleveland’s criminal underworld during the 1970s. His life was marked by a blend of ruthless ambition, charisma, and a relentless pursuit of power.
Early Life
Born in Cleveland, Ohio, Danny Greene grew up in a turbulent environment after being abandoned by his father following his mother’s death. Raised in an orphanage and later by his grandfather, Greene’s early life was shaped by hardship and instability. These experiences fostered a tough and rebellious spirit, leading him into criminal activities at a young age.
Union Leadership and Corruption
Greene’s criminal career began in earnest when he became involved in union activities. He rose to prominence as the leader of the Longshoremen’s Local 1317, where he wielded significant influence. However, his tenure was marred by allegations of corruption, embezzlement, and violent enforcement tactics.
Greene’s control over the union made him a formidable player in Cleveland’s labor market and gave him a foothold in organized crime.
Rise in the Cleveland Underworld
In the 1970s, Greene’s ambitions extended beyond the labor unions. He established his own gang and engaged in various criminal enterprises, including extortion, racketeering, and loan sharking. Greene’s activities brought him into direct conflict with the Cleveland Mafia, leading to a violent power struggle. Despite numerous assassination attempts, Greene managed to survive multiple car bombings, earning a reputation for being seemingly indestructible.
Feud with the Mafia
The conflict between Danny Greene and the Cleveland Mafia escalated into a full-scale gang war. Greene’s defiance and his ability to survive attempts on his life made him a legendary figure. His war against the Mafia was characterized by frequent bombings and shootings, creating a climate of fear and chaos in Cleveland.
Assassination
On October 6, 1977, Danny Greene’s luck finally ran out. He was killed by a car bomb outside his dentist’s office in Lyndhurst, Ohio. The assassination was orchestrated by Mafia operatives, bringing an end to Greene’s tumultuous and violent career.
Last Words
These Irish mobsters left an indelible mark, from Billy the Kid’s Wild West antics to Whitey Bulger making waves during Prohibition. Their stories are intriguing tales of defiance against authority. These guys came up tough and turned to crime as the surest path to power, driven by harsh reality and ambition in equal measure.
Think of Ned Kelly facing off with cops in armor of his own making, or Mickey Spillane ruling his New York turf through fear and favor alike. But they were products of their era too, mirroring the struggles of Irish immigrants and their descendants in America.
Their lives were a mix of cutthroat schemes, bloody showdowns, and relentless desire for control. And their legends still captivate, shedding light on a world where survival meant making your own breaks regardless of laws or norms.