James 'Whitey' BulgerBulger 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.
James 'Jimmy the Gent' BurkeBruke 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.
Edward J. 'Eddie' McGrathEddie 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.
- 9Winter 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.
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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