Famous Irish gangsters in America, with photos (yes, some are mug shots). These are the notorious godfathers - the top crime bosses from the Irish Mob and associated crime syndicates, listed from earliest to most recent. Who are the most infamous Irish mobsters in U.S history? Narrowing down a list isn't easy. From Chicago to Boston to Philadelphia, Irish mobsters have controlled everything from bootlegging (during Prohibition years) to horse racing, and everything in-between. This list of gangsters includes all of the top Irish mobsters in US crime history. From Bugler to Spillane, check out this list of infamous Irish mob members. I compiled this gangster list from a bunch of sources.
Mickey Spillane came to power as an Irish mobster in the 1960s and 1970s. Spillane took over from Eddie McGrath, running rackets throughout Hell's Kitchen and well beyond. He was a night club owner and a numbers guy - and he was battling to keep his position as boss, with challenges coming from violent Irish mobsters who wanted nothing more than to take over. Among them: James 'Jimmy' Coonan, who wanted revenge on Spillane for kidnapping his accountant father. Spillane was said to be involved in the so-called "snatch" racket - kidnapping big businessmen in the area and then demanding ransom from other mob groups. Mickey Spillane was murdered in May of 1977, clearing the way for a whole new kind of gangster to emerge.
2
Owney 'The Killer' Madden
Owney Madden was the boss of 'The Westies,' a group that ruled supreme over Hell's Kitchen - and eventually controlled a large part of Manhattan. Madden was much more than a mere Irish street gang mobster and bootlegger. He controlled an interest in Harlem's famed Cotton Club, among other things. Remember Francis Ford Coppola's 'The Cotton Club' movie? Actor Bob Hoskins portrayed Owney Madden in the film. Madden was heavily involved in all aspects of Irish mob activity, but in 1932, he was implicated in the murder of mobster Vincent 'Mad Dog' Coll, spent a year behind bars and, afterward, retired to Arkansas to live out his golden years.
3
James 'Jimmy' Coonan
Jimmy Coonan is considered one of the most most violent and ruthless Irish mobsters ever. Coonan took over the Hell's Kitchen Irish mob after Mickey Spillane's 1977 murder. His reign lasted through the mid-1980s, during which time he was purportedly involved in countless murders, and, notably, drugs. Prior to Coonan, Irish gangsters in Hell's Kitchen weren't really involved in illegal drugs. This all changed under Coonan, who forged an alliance with the Gambino crime family in the late 70s, strengthening his own power. Coonan was incarcerated more than once for his crimes, and eventually, his right-hand man flipped on him. He was arrested in 1986 and sentenced to 75 years behind bars. He's serving his time at the Lewisburg Federal Penitentiary.
4
George 'Bugs' Moran
""Bugs"" Moran was a gangster during the Prohibition era in Chicago. After embarking on a criminal career as a teenager, he gained a reputation as a lunatic with a ferocious temper, earning the nickname ""Bugs"" (at the time, slang for ""crazy."") Before the age of 21, he had already been incarcerated three times.
During Prohibition, Moran found his own bootlegging operation in direct competition with the Chicago ""Italian"" family set up by Al Capone, triggering a turf war (and lifelong rivalry) between the two men. Their back-and-forth series of attacks and retaliations lasted through the rest of the Prohibition era, and led Moran to popularize the technique of driving by Capone's properties and peppering them with gunfire, an iconic image of organized crime from the era and the inspiration behind the crime of ""drive-by shooting."
Moran was convicted of robbing a bank messenger in Ohio in 1946, and spent most of the remainder of his life in prison. He died destitute in 1957, mere weeks after beginning a new prison sentence for bank robbery.
Dean O'Banion (sometimes referred to as Dion O'Banion) was a native of Chicago's North Side neighborhood and, during the beginning of the Prohibition era, united with Italian South Side mobsters (including boss "Papa"Johnny Torrio and his associate, Al Capone), to ramp up their bootlegging operations and avoid turf battles. In 1924, O'Banion decided to break with his former partners, and unsuccessfully attempted to frame Torrio for murder, leading to a bloody struggle for dominance of North Side bootlegging.
In November of 1924, O'Banion was shot and killed while working in his flower shop. The murder started a gruesome 5-year Chicago gang war that culminated in the infamous St. Valentine's Day Massacre in 1929.
O'Banion was the basis for the character played by Jimmy Cagney in the 1931 film "The Public Enemy."
6
James 'Whitey' Bulger
Bulger spent his early years in the Air Force, though he was frequently in trouble for going absent without leave and starting fights. He was honorably discharged in 1952 and embarked on a criminal career. (There is some indication he may have been involved in the CIA's MK-ULTRA program, researching mind-control and psychedelic drugs.) He also spent some time during this era as an inmate on Alcatraz Island.
In the 1970s, Bulger worked as an enforcer for Donald Killeen, a South Boston crime boss. He would later change sides and begin working for How Winter and his "Winter Hill Gang," and some have suggested he got this job by murdering his old boss Donald Killeen, though this has been disputed. While rising within the Winter Hill Gang's organization, some time in the mid-1970s, Bulger also became an FBI informant. In the ensuing years, he also became heavily involved in narcotics trafficking, even allegedly selling PCP to children!
In '94, a joint DEA, Massachusetts and Boston Police probe into Bulger's gambling and drug operations was launched, and the man himself fled Boston and went into hiding. Bulger was finally taken into custody on June 21, 2011, in Santa Monica, California. At the age of 81, the former mob boss, suspected of playing a role in 19 murders, will now face the music for his alleged crimes.
7
James 'Jimmy the Gent' Burke
Bruke was an associate (though not a member) of the Lucchese Italian crime family, and is most famously one of the men thought to be involved in the 1978 robbery at JFK International Airport known as the Lufthansa Heist. He was the inspiration for the character Jimmy Conway (played by Robert DeNiro) in the Martin Scorsese film "Goodfellas."
Burke started his criminal career as a teenager, passing bad checks in and around his home in Rockaway, Queens. After spending 5 years in prison for passing counterfeit checks (during which time he refused to rat on his associates), Bruke moved up in New York's Mafia circles.
Following his release from prison, Burke was allegedly involved in assassinations and also took up distribution of illegal untaxed cigarettes and liquor. He also started a lucrative enterprise hijacking delivery trucks. (His tendency to tip the drivers after stealing their cargo earned him the "Gent" nickname.)
Following the theft of nearly $6 million in cash and jewels from the Lufthansa cargo terminal at JFK (the largest robbery in American history at the time), Burke is alleged to have systematically assassinated many of his primary associates in an effort to cover up the crime. Burke was arrested in 1980 based largely on the testimony of his colleague Henry Hill, who had turned FBI Informant and joined the witness protection program. He was eventually convicted of a 1978 gambling scam involving Boston College basketball games, as well as the murder of conman Richard Eaton. He was sentenced to life in prison, and died of lung cancer in 1996.
8
Edward J. 'Eddie' McGrath
Eddie McGrath took the reins of 'The Westies' when Owney Madden retired, controlling the Irish mob in New York's Hell's Kitchen in the 1940s and 1950s. McGrath was a union guy and worked as an organizer for the International Longshoremen's Association (ILA) along the Hell's Kitchen waterfront. McGrath eventually retired to Florida (where else?) in 1959. His successor, Mickey Spillane, was to become one of the most notorious Irish mobsters in U.S. history.
Winter got his start in organized crime under the tutelage of gang leader Buddy McLean in Somerville, Massachusetts. After McLean's death in 1966 outside the Tap Royal social club, Winter took over for him. After Winter was arrested in 1979 for fixing horse races, leadership of the gang was passed down to James "Whitey" Bulger. Winter was released in 1987, but jailed again in 1993 for dealing cocaine. (At the time, he was offered a deal in exchange for snitching on Bulger. Winter refused.)
Winter was again released from prison in 2003, and currently lives in Massachusetts.
10
James 'Buddy' McLean
McLean is best-known as the founder and original leader of the "Winter Hill Gang" of Somerville, Massachusetts. The gang had started in 1955, when McLean attracted compatriots due to his infamy as a tough street fighter. Originally, Winter Hill members focused their efforts on the numbers racket, loansharking and hijacking trucks.
McLean became embroiled in a rivalry with another group of mobsters from nearby Charlestown, particularly relating to the murder of George McLaughlin. In October of 1961, he shot and killed McLaughlin's brother, Bernie, in the streets of Charlestown in front of many witnesses, but was acquitted of all charges. (His alleged accomplice in the crime was a man named Alex Petricone, who became an actor and changed his name to Alex Rocco.)
McLean was killed in 1966 outside the Tap Royal Social Club (a known hangout of the Winter Hill Gang) by Steve and Cornelius Hughes. He was succeeded by Howie Winter.
A surprisingly educated and sophisticated gangland figure, John Patrick Looney was admitted to the Illinois Bar in 1889, was active in Democratic Party politics and had started his own newspaper - the Rock Island News of Rock Island, Illinois - in 1905. He would go on to use the publication to extort powerful local residents (threatening to publish unflattering stories unless he received a payoff) and to attack other personal enemies. Looney eventually sold his stake in the paper in 1908, though he continued to harass and threaten the purchaser - W.W. Wilmerton - who had hoped to dismantle it. (He even got into a gunfight with Wilmerton at one point during which Looney was wounded.)
During and following his tenure at the Rock Island News, Looney got involved in gambling and prostitution as well as his extortion ring. Once Prohibition became the law of the land, he extended his enterprise into the protection racket as well, offering cover for law violators.
In 1922, his fortunes changed after Looney allegedly killed William Gabel, a man who had provided evidence against Looney to Prohibition agents. In retaliation, Looney's son was murdered by rivals, and police raids shut down his speakeasies and brothels. Though he fled, first to Canada and then New Mexico, Looney was eventually apprehended, convicted of Gabel's murder as well as "conspiracy to protect gambling, prostitution and illicit liquor traffic" and sentenced to 14 years in prison. He died in 1947 in a tuberculosis sanitarium.
Looney is the inspiration for Paul Newman's character, John Rooney, in the Oscar-winning 2002 movie "Road to Perdition." The character was originally named "John Looney" in Max Allan Collins' graphic novel of the same name.
12
James 'Big Jim' O'Leary
Big Jim O'Leary was a powerful Irish mob boss in Chicago for over a decade, controlling gambling on the city's South Side with an iron fist.
His criminal career started as a teenager, when O'Leary worked for bookies in Long Beach, Indiana. He later began operating his own illegal gambling ring on the steamship The City of Traverse on Lake Michigan. Both of these early operations failed to gain traction, largely because of O'Leary's refusal to pay off local police. He only found financial success following the death of Chicago crime lord Michael Cassius MacDonald, which led to O'Leary's assuming control of gambling in Chicago's South Side.
And yes, if the O'Leary/Chicago connection seems familiar, it should: Big Jim's parents, Patrick and Catherine O'Leary, owned the barn where the infamous Great Chicago Fire in 1871 is thought to have started. Though it's never been proven, their cow was supposedly the arsonist responsible.
13
Edward 'Eddie the Butcher' Cummiskey
A fixture in the Hell's Kitchen neighborhood in the 1960s, Eddie Cummiskey gained attention first as an associate of Mickey Spillane. A brutal man who had gained knowledge of butchery while in prison in Upstate New York, Cummiskey became an integral part of Spillane's operation. (He's credited with developing the practice of butchering murder victims and disposing of their remains in the Hudson River, an iconic image of New York gangster-dom.)
Cummiskey and Spillane split in the 1970s after Cummiskey took a young James Coonan under his wing. Nonetheless, Cummiskey was killed in 1976 by Joseph "Mad Dog" Sullivan during a purge of Spillane's close associates ordered by Anthony "Fat Tony" Salerno.
14
Kevin Kelley
Kevin Kelley took over operations of the Irish mob in Hell's Kitchen when Jimmy Coonan was sent up the river. He'd been a made man under Coonan for years, so he was ready to move in. Kelley expanded the Irish mob's influence well beyond the West Side of NYC by selling illegal drugs, mainly cocaine. Kelley's reign was a short one - he was immediately fingered by the FBI and he and his associate, Kenny Shannon, eventually turned themselves in to authorities in 1988.
Mickey Spillane came to power as an Irish mobster in the 1960s and 1970s. Spillane took over from Eddie McGrath, running rackets throughout Hell's Kitchen and well beyond. He was a night club owner and a numbers guy - and he was battling to keep his position as boss, with challenges coming from violent Irish mobsters who wanted nothing more than to take over. Among them: James 'Jimmy' Coonan, who wanted revenge on Spillane for kidnapping his accountant father. Spillane was said to be involved in the so-called "snatch" racket - kidnapping big businessmen in the area and then demanding ransom from other mob groups. Mickey Spillane was murdered in May of 1977, clearing the way for a whole new kind of gangster to emerge.
Owney Madden was the boss of 'The Westies,' a group that ruled supreme over Hell's Kitchen - and eventually controlled a large part of Manhattan. Madden was much more than a mere Irish street gang mobster and bootlegger. He controlled an interest in Harlem's famed Cotton Club, among other things. Remember Francis Ford Coppola's 'The Cotton Club' movie? Actor Bob Hoskins portrayed Owney Madden in the film. Madden was heavily involved in all aspects of Irish mob activity, but in 1932, he was implicated in the murder of mobster Vincent 'Mad Dog' Coll, spent a year behind bars and, afterward, retired to Arkansas to live out his golden years.
""Bugs"" Moran was a gangster during the Prohibition era in Chicago. After embarking on a criminal career as a teenager, he gained a reputation as a lunatic with a ferocious temper, earning the nickname ""Bugs"" (at the time, slang for ""crazy."") Before the age of 21, he had already been incarcerated three times.
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