James Whitey Bulger

20 Boston Irish Gangsters

The Irish mob has a stronger presence in Boston than any other city in America. It is the Irish gangsters like Whitey Bulger who dominated the headlines over the years. South Boston aka “Southie” and it’s neighboring town Dorchester are the Irish mob hot spots in the city, going back at least a century.

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 (born 1956) Kevin Weeks served as Whitey Bulger’s enforcer in the 1970’s and 1980’s. 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. Unlike most mob turncoats Weeks went back to his old stomping grounds in Southie, seemingly with little fear of his safety. He has appeared on various documentaries and local news interviews. He has stayed out of trouble by all accounts for the last several years.

Howard “Howie” Winter (born 1929) – Howie Winter was the boss of the powerful Winter Hill Gang in the 1970’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 in 1966, Winter took over the Winter Hill Gang, which was not named after him.

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. Bulger would soon take over the gang. Howie Winter knew he’d been betrayed but refused to become a “rat” himself, instead opting to spend years in prison.

He was a free man by 1987 and decided to leave Boston for St. Louis where he resumed his criminal activities. He soon went back to prison for narcotics trafficking. He was again offered a deal to testify against Bulger and Stephen Flemmi, but he declined and served another nine years. He is currently 90 years old and living back in Milbury, Massachusetts.

Edward “Wimpy” Bennett (died 1967) – Wimpy Bennett was the most powerful Irish mobster in Boston in the 1950’s and early 1960’s. He was involved in the famous Brinks robbery in 1951. 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.

Wimpy Bennett and his two brothers Walter and William were all murdered in 1967 during the middle of the McLean/McLaughlin War. It was a sad year for the Bennett family and put a microscope on just how bad the war had gotten with some 60 men killed. Bodies were being found in the streets on a weekly basis at this time around Boston.

It was their former underling Stephen “The Rifleman” Flemmi who betrayed the brothers and participated in all of their murders. He was being protected by a crooked FBI agent named H. Paul Rico. Rico just simply looked the other way while his star informant disposed of the Bennett brothers and many others.

Whitey Bulger
America’s Most Wanted Gangster & the Manhunt That Brought Him to Justice is the most up to date and complete story of Bulger and the Boston mob. Link is to Amazon

Ronald Dermody (died 1965) – Dermody was a bank robber who was fresh out of prison in the early 1960’s. Dermody was affiliated with the McLaughlin brothers and looking to gain traction. He decided the best way to do that was to kill their biggest enemy. He went on a mission to kill Buddy McLean but instead shot the wrong man.

After the shooting, word got around to McLean about his real intentions, which made Dermody a marked man. Dermody then got scared and called Boston FBI agent H. Paul Rico looking for help. Instead of helping him, Rico alerted McLean who shot Dermody to death at the meeting site where he was supposed to meet with Rico.

Harold Hannon (1937-1964) – Harold Hannon was an enforcer for the McLaughlin brothers in Charlestown during the 1950’s and early 1960’s. After a tough street fighter named Tommy Sullivan put a public beating on Punchy McLaughlin in 1957, Hannon hunted down Sullivan and killed him. Hannon was the most feared shooter on the McLaughlin side early on.

Hannon and his friend Willie Delaney were set up by Buddy McLean and the feared Joe “The Animal” Barboza in 1964. A good looking lady willing to have sex with both men lured them back to an apartment. Hannon suffered a horrific death. Medical examiners concluded that a blowtorch had been used on his genitals.

It was a horrific murder scene. They had come to get revenge for Tommy Sullivan murder 7 years before. While Hannon was tortured for hours, McLean decided to go easier on Willie Delaney, who just happened to be with Hannon. He gave Delaney a bottle of liquor and a handful of sleeping pills before strangling him.

Arthur “Butchie” Doe Jr. (1959-2018) – Arthur Doe Jr., also known as Butchie was a chronic bank robber and involved in union corruption. His father Arthur Sr. was involved in the McLean-McLaughlin War of the 1960’s. Butchie lived a very violent life, having killed three people. He also survived three very high profile attempts on his own life.

Arthur "Butchie" Doe
Arthur “Butchie” Doe

He was shot three separate times within a year back in 1989-1990. Butchie was a regular in the Boston Herald and Boston Globe in those days. After one of the incidents, an unknown man called the hospital and said there was no reason to stitch him up as they were only going to come after him again.

He had ripped off some old partners and had many people looking for him. One time, he was shot after coming out of hiding to get a sandwich. Somehow, Doe was able to survive all the attacks and eventually things died down as the gangster culture in Boston died out. Butchie Doe passed away from cancer in 2018.

Cornelius “Connie” Hughes (died 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. Suddenly dozens of bullets were being sprayed into Hughes’ car. He violently crashed into a guardrail and died on the scene. Notorious killer Joe “The Animal” Barboza was the man who killed Connie, but he wasn’t done with the Hughes brothers yet.

Stevie Hughes (died 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. They were quick with a gun and always together looking for enemies. By killing Buddy, the Hughes brothers were the most wanted men by the McLean side.

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. Him and his passenger were killed. It was Joe Barboza again who did the job.  

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 operated out of his own bar in Southie called the Transit Cafe.

Killeen’s main rivals were a group known as the Mullen Gang. A young Whitey Bulger was part of Killeen’s crew, as was the feared hitman William O’Sullivan. Pat Nee was a member of the opposing Mullens and found himself at war with Whitey in these days. They would later work together.

Unfortunately for Killeen, the youngsters wanted the power and saw the war as an opportunity to seize power. His brother Edward was murdered in 1968. Donald Killeen would be murdered in 1972. The other brother Kenny would be warned by Whitey Bulger that he was “out of business, no further warnings”. He heeded the warning.

William O’Sullivan (1928-1971) O’Sullivan was a member of the Killeen Gang. He operated both out of Southie and the Savin Hill section of Dorchester. He was the original mentor for a younger rising mobster named James “Whitey” Bulger. O’Sullivan was the main muscle for the Killeens who were at war with an ambitious young crew known as the Mullen Gang.

The gangs were fighting for turf in Southie and O’Sullivan teamed up with Whitey to gun down several Mullen members. It all came crashing down for O’Sullivan on March 28, 1971. He had been warned by his protege Bulger to lay low but O’Sullivan refused and as a result was gunned down right in front of his family home.

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, one of its’ charter members. Joe Mac was a WWII veteran and also a ruthless killer at the same time.

He would get indicted in the infamous horse race fixing scandal in 1979. McDonald didn’t know at the time that he was being betrayed by two Winter Hill underlings, Whitey Bulger and Stephen Flemmi. He decided to go on the lam, and while in hiding committed a murder for 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.

The-Irish-King-Of-Winter-Hill
The Irish King Of Winter Hill is available on Amazon.

James “Buddy” McLean (1929-1965) – Buddy McLean was the original boss of the Winter Hill Gang. Buddy had a handsome baby face but was a feared streetfighter. Among his gangster peers, Buddy was revered for his extreme toughness and loyalty. In the early 1960’s a major gang war broke out between McLean and a group from Charlestown led by the McLaughlin brothers.

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. McLean’s top hitman Joe Barboza would kill both Hughes brothers the same year.

The war had started when a drunken George McLaughlin had groped a girlfriend of one of Buddy’s friends. He was given a beating. George’s brother Bernie vowed revenge and when McLean wouldn’t give up his friends, the war began. McLean initially tried to peacefully resolve the issue until he found that the McLaughlins put a bomb under his family car.

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.