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20 Boston Irish Gangsters

Apr 23

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James “Whitey” Bulger (1929-2018) - Whitey Bulger was by far the most well known and powerful mobster in the history of the New England mob. He didn’t get to that spot without some serious help though. He was an FBI informant for decades and received special treatment from them. He was often tipped off about the activities of his rivals and more than once was given a heads up about potential informants. 


All Whitey had to do was provide information about the Boston FBI’s real target, the Italian mafia. Bulger used the relationship to strengthen his position in organized crime. He became the leader of Boston’s Winter Hill Gang. His FBI contact John Connolly gave him advanced warnings when indictments for racketeering were about to come down in 1994. 


Bulger went on the run and stayed gone for 16 years. He was the FBI’s #2 most wanted man until Osama Bin Laden was killed, and then he was #1. He was caught in 2011 in California. He was convicted of involvement in 11 murders and sent to prison. In 2018, he was beaten to death by another prisoner in West Virginia, the very same day that he was put into general population. 


Kevin “Two Weeks” Weeks - Kevin Weeks served as Whitey Bulger’s enforcer in the 1970s and 1980s. Kevin was a member of the infamous Winter Hill Gang, Boston’s mainly Irish organized crime gang. Whitey and Kevin extorted local Southie drug dealers, demanding a cut of all their sales. He assisted Whitey in the murder of Brian Halloran and many other violent crimes. 


After going to prison for racketeering in 1999, he agreed to cooperate with the FBI after being locked up for just two weeks. He had a good reason though, he had just found out that his bosses Whitey Bulger and Stephen “The Rifleman” Flemmi were both informants. Weeks was released in 2005 and retired from mob activity.


His testimony helped to convict Steve Flemmi and corrupt FBI agent John Connolly away. Weeks led authorities to several buried bodies around Boston. Eventually Bulger was caught, but not right away. Kevin always thought he was going to come back at some point for revenge. 


Howard “Howie” Winter (1959-2012) - Howie Winter was the boss of the powerful Winter Hill Gang in the 1870’s. He had gotten his start in the mob as an associate of legendary gangster James “Buddy” McLean in the early 1960’s. When McLean got killed, Winter took over the Winter Hill Gang. He was sent to prison in 1979 for fixing horse races. He would find out later that two of his gang members, Whitey Bulger and Stephen Flemmi had been informing on him. 


Edward “Wimpy” Bennett (died 1967) - Edward “Wimpy” Bennett was the most powerful Irish mobster in Boston during the 1950s and early 1960s. He was involved in the famous Brinks robbery in 1951. Wimpy had two brothers that assisted him and a crew. One of his crew in the early days was a young Steve Flemmi. 


Bennett was not a fan of the Italian mafia and wanted to run them out of Boston, which he may have done if the FBI didn’t want the Italians for themselves. Bennett and his two brothers Walter and William were all murdered in 1967. Unfortunately, the betrayal of crew member Stephen Flemmi and the actions of a crooked FBI agent named H Paul Rico led to the complete demise of the Bennett brothers. 


Ronald Dermody (died 1965) - Dermody was a bank robber who was fresh out of prison in the early 1960’s. He was on a mission to kill Buddy McLean but instead shot the wrong man. Dermody then got scared and called Boston FBI agent H. Paul Rico looking for help. Instead of helping Dermody, Rico alerted McLean who shot Dermody to death at the meeting site where he was supposed to meet with Rico. 


Wilfred “Willy” Delaney (1937-1964) - Willy Delaney was an enforcer for the McLaughlin brothers in Charlestown during the 1950’s and early 1960’s. After a tough as nails street fighter named Tommy Sullivan put a public beating on Punchy McLaughlin in 1957, Delany hunted down Sullivan and killed him. After being set up by Buddy McLean, Delaney suffered a horrific death in 1964. Medical examiners concluded that a blowtorch had been used on his genitals. 


Arthur “Butchie” Doe Jr. (1959-2018) - Arthur Doe Jr., also known as Butchie was a bank robber and involved in union corruption. His father had been killed during the McLean-McLaughlin War of the 1960s. Butchie lived a very violent life, having killed three people. He also survived three very high profile attempts on his own life. He was shot three separate times within a year back in 1989-1990. 


Doe passed away of natural causes in 2018. He was known as a very solitary guy. By all appearances, Butchie seemed to finally calm down and live his last years in a more civilized manner. A long ways from when he was on the front pages of the Boston Herald and Boston Globe during his most violent years. 


Cornelius “Connie” Hughes (died May 1966) - Connie and his brother Stevie Hughes were by far the most feared members of the McLaughlin crew. When someone needed to be hurt or killed, the job was usually given to the eager brothers. The Hughes brothers were responsible for the majority of the killings coming from the McLaughlin side of the war. Connie was driving home on May 25, 1966 when a car pulled up alongside his. Notorious killer Joe “The Animal” Barboza was the man who killed him. 


Stevie Hughes (died September 1966) - Stevie Hughes was the man who killed Buddy McLean in 1965, among many others. He and his brother Connie served as the main muscle for the McLaughlins. The Hughes brothers were feared all throughout the Boston underworld. After his brother was gunned down in May of 1966, Stevie was now missing his layers of protection. 


Connie, Punchy and Bernie McLaughlin were all dead. Stevie was driving in Middleton, Mass on September 23, 1966 when a car pulled up beside him and bullets rang out. It was Joe Barboza again who did the job. Barboza was on a killing spree that year, having killed both Hughes brothers in the space of four months. 


The death of Steve and Connie Hughes was a major shift of power in the McLean vs McLaughlin war. The brothers were poised to take over the McLaughlin side until they were wiped out. The war would go on for another year or two before finally dissolving. 


Donald Killeen (1923-1972) - Donald Killeen was one of three Killeen brothers who controlled the bookmaking and loansharking rackets in South Boston during the 1950’s and 1960’s. Killeen’s main rivals were a group known as the Mullen Gang. A young Whitey Bulger was part of Killeen’s crew. Unfortunately for Killeen, the youngsters wanted the power and two Killeen brothers would be murdered in the early 1970’s. The other brother would be warned by Whitey Bulger that he was “out of business, no further warnings”. 


Johnny Martorano - Born in 1940, Johnny Martorano was the one of the deadliest hitmen in the history of the New England mob. He has admitted in court to being involved in 20 murders, all of which were mob related. Johnny’s father was an old time mobster who groomed his son for a life of crime. Martorano became an enforcer for the Winter Hill Gang. 


After learning that his bosses Bulger and Flemmi were informants, Martorano became a government witness. Martorano had been assigned by Winter Hill to kill John Callahan and Oklahoma businessman Roger Wheeler. Martorano appeared on 60 Minutes back in 2008, discussing how a former alter boy became a mafia hitman and then a government witness. 


Joseph “Joe Mac” McDonald (1917-1997) Joe Mac was the best friend and partner in crime of James “Buddy” McLean and a mentor to Howie Winter. McDonald was the man who actually organized the Winter Hill Gang. He would get indicted in the horse race fixing scandal in 1979. He decided to go on the lam, and while in hiding committed a murder for Whitey Bulger in Oklahoma. McDonald would die of natural causes- a stroke, in 1997.


Bernie McLaughlin (died 1961) - Bernie McLaughlin was the leader of the McLaughlin brothers and the most powerful gangster in Charlestown. When he found out his brother George had been beaten senseless by some friends of Buddy McLean, he set out for revenge. After trying to blow up McLean’s family car, Bernie himself was hunted down and killed by McLean in 1961. The war continued to rage after his death. 


Ed “Punchy” McLaughlin (died 1965) - Ed McLaughlin was known as “Punchy”. He was a former boxer turned street enforcer known for violent and unpredictable behavior. Puchy had been in many bloody street fights. When the McLean-McLaughlin War broke out, Punchy was right in the middle of it, killing McLean’s friend Russell Nicholson. Punchy was gunned down in 1965 at a bus stop while on his way to his brother George’s murder trial. The shooter was Stephen Flemmi. 


George McLaughlin - It was George McLaughlin’s drunken and disrespectful behavior that started the McLean-McLaughlin War. He groped an associate’s girlfriend and received a beatdown that almost killed him. A street war ensued and bullet riddled bodies started turning up all over the streets of Boston. Ironically, George was the only brother to survive the war, it is unclear if he’s still alive today. He would be in his early 90’s. 


James “Buddy” McLean (1929-1965) - Buddy McLean was the original boss of the Winter Hill Gang. Winter Hill ran the rackets in Boston. They worked with and for the Patriarca Family but Winter Hill had a huge share of control. Buddy had a handsome babyface but was a feared streetfighter. McLean was one of the most important gangsters in Boston history. 


In the early 1960s a major gang war broke out between McLean and a group from Charlestown led by the McLaughlin brothers. The war had started when a drunken George McLaughlin had groped a girlfriend of one of Buddy’s friends. Georgie was given a vicious beating but not killed. George’s brother Bernie McLaughlin vowed revenge and when McLean wouldn’t give up his friends, the war began. 


Some 60 men died in the next couple years as the two sides hunted each other. In the end, Buddy McLean and two McLaughlin brothers, Bernie and “Punchy” were killed. McLean was shot and killed on October 31, 1965 by McLaughlin enforcer Stevie Hughes.


Patrick Nee - Patrick Joseph Nee is a retired former Winter Hill Gang member. He was at one time a heated rival of Whitey Bulger but eventually joined forces with him after Whitey took over the gang. Nee was a supporter of the IRA and spent a significant amount of his efforts raising money to send them firearms. He was involved in the murder of Arthur “Bucky” Barrett in 1983, along with Bulger enforcer Kevin Weeks. He was suspected in multiple other murders but never charged.


Russell Nicholson (1931-1964) Russell Nicholson was a police officer, but also a close associate and actual member of the Winter Hill Gang. Nicholson was with Buddy McLean the day that Bernie McLaughlin was killed outside of the Morning Glory Cafe in Charlestown. A huge crowd witnessed the murder but no one cooperated. Nicholson would be murdered three years later by George and Punchy McLaughlin, avenging their brother’s death. 


James “Spike” O’Toole (1929-1973) - He was a close friend of Buddy McLean and a member of the Winter Hill Gang. O’Toole was actually murdered by his own men. His killer was Johnny Martorano. In a brutal killing, Martorano actually ran over O’Toole with his car after walking out of a bar in Dorchester. It was a love triangle that got O’Toole killed, another Winter Hill member wanted his lady. 


John “Red” Shea - Red Shea is a retired gangster from South Boston who was once a part of the infamous Winter Hill Gang. He grew up in Southie and came up under Whitey Bulger’s wing. Shea was given 12 years for trafficking in cocaine. While in prison, stories about Bulger being an informant came out. Shea turned his back on organized crime. He wrote a book called Rat Bastards: The Story Of South Boston’s Most Honorable Irish Gangster.

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