Billy the Kid to Whitey Bulger, the ten Irish outlaws who lived outside the law

Rebellion runs deep in the Irish story, and for ten notorious figures, it spilled over into outright criminality on three continents. Their ranks include Billy the Kid, the Wild West legend raised in a New York slum by an Irish immigrant mother, Ned Kelly, the son of Tipperary emigrants who came to embody the rebellious Australian spirit, and Grace O’Malley, the 16th-century sea pirate whose fame reached all the way to the court of Queen Elizabeth I.

From Wild West legend Billy the Kid to the ruthless Boston mobster James "Whitey" Bulger, and even Grace O'Malley, the famous Pirate Queen, these individuals have left lasting legacies in criminal history. Their stories span across continents, showcasing the deep ties between Irish heritage and outlaw life.

Billy the Kid

(1859–  1881)

Billy the Kid's real name was William McCarty. Billy has become one of the legendary figures of the Wild West. His mother was an Irish immigrant who grew up in Ireland and raised her son in a New York slum before heading out west.

Ned Kelly

(1855 – 1880)

Ned Kelly is an iconic figure of Australian legend. The son of Tipperary emigrants who has come to symbolize the rebellious Australian spirit

James 'Whitey' Bulger

(1929 - 2018)

James 'Whitey' Bulger was a Boston mafia kingpin who is reputed to have killed or ordered the killings of up to fifty people. He was killed while in prison in 2018.

The Pirate Queen

(1530 -1603)

Grace O'Malley is the Irish sea pirate of the 16th century. Her fame became such that Queen Elizabeth I summoned her to London in order to meet her. The Broadway Show "The Pirate Queen" was based on her life. This strong Irish woman (and pirate) even has a whiskey named after her. There is also a notable statue of Grace O'Malley that stands at Westport House in County Mayo, honoring her deep ties to Umhaill and Clew Bay.

Emmett Dalton

 (1871-1937)

The Dalton gang was also known as the 'Wild Bunch', one of the most famous train robber families in American history. Emmett Dalton was a ringleader and the only survivor of the famous Coffeyville shootout in 1892. 

James Freney

(1719–1788)

James Freney was an Irish highwayman. The most famous of that era, his family in Kilkenny had their lands taken from them by the English, and Freney took to highway robberies to get revenge. Pursued all over Ireland, he managed to escape into exile, but his body was later brought back to Kilkenny, where he is still alive in the folk memory there.

John "Legs" Diamond

(1897 - 1931)

John "Legs" Diamond's real name was Jack Moran, and he was the son of an Irish immigrant. Also known as Gentleman Jack, he was a famous Irish American gangster and bootlegger in New York City during the Prohibition era. Famous for surviving numerous attempts on his life.

Owney "The Killer" Madden

(1891–1965)

Owney "The Killer" Madden was a leading underworld figure in Manhattan, most notable for his involvement in organized crime during Prohibition. He also ran the famous Cotton Club and was a leading boxing promoter in the 1930s. Though English-born, his parents were both from Ireland.

Charles Dean O'Banion

(1892 – 1924)

Charles Dean O'Banion was an Irish American mobster who was the main rival of Al Capone during the brutal Chicago bootlegging wars of the 1920s. The newspapers of his day called him Dion O'Banion, although he never went by that name.

Michael Spillane

(1934 – 1977)

Michael Spillane was an Irish-American mobster from Hell's Kitchen. Spillane, who was called the "last of the gentleman gangsters," was a marked contrast to the violent Westies gang members who succeeded him in Hell's Kitchen.

* Originally published in 2016, updated in 2026.