Kevin KelleyKevin 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.
Edward 'Eddie the Butcher' CummiskeyA 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.
James 'Big Jim' O'LearyBig 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.
John Patrick LooneyA 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.
James 'Buddy' McLeanMcLean 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.
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