Howard "Howie" Winter (born 1929) is an Irish-American mobster and onetime Boss of the Winter Hill Gang.
Winter was born in Boston on St. Patricks Day 1929 to a German father and an Irish mother in the Somerville section of Massachusetts. Winter became one of the original members of the Winter Hill Gang and was the protégé of the Gang's first boss James "Buddy" McLean. Other originating gang members, along with Winter and McLean, were Salvatore Sperlinga, Americo Sacramone, Anthony "Tony Blue" D'Agostino, Thomas Ballou Jr., "Joe Mac" Joseph McDonald, Russel Nicholson, and James "Spike" O'Toole.
The Irish Gang Wars
During the bloody Irish gang wars of the 1960's and 1970's, Winter was a heavy hitter for the Winter Hill Gang and proved his worth to the gang on numerous occasions. On October 11th, 1965, Winter's life and the history of the Winter Hill Gang would change forever.
The Hughes Brothers, Stevie and Connie who were vicious killers for the McLaughlin's Charlestown Irish Mob were able to kill Winter Hill Gang Boss James "Buddy" McLean during what became known as Boston's Irish Gang Wars. The McLaughlin brothers believed that by murdering Buddy McLean the Winter Hill Gang would fall into disarray through lack of leadership and would be out of the equation once and for all. This wasn't to be the case, Howard "Howie" Winter was prepared to not only sit in the Winter Hill Gang's thrown as king but he would also plan to defeat the McLaughlin brothers once and for all.
From 1965 until 1979, Winter would be the undisputed boss of the Winter Hill Gang. One of the leaders of the Charlestown mob, "Punchy" Edward McLaughlin, had survived many assassination attempts by different members of the Winter Hill Gang and in one attempt he had actually lost a hand. On October 20th, 1965 just 9 days after the murder of Buddy McLean, Punchy was on his way to a court house for his brother's murder trial when he was murdered at a bus station in West Roxbury, Massachusetts. Many people believe that Howie Winter was the gunman behind the rub-out, and that the murder was what elevated Winter to the number one spot in the Winter Hill Gang.
In 1966, Winter ordered the murders of the Hughes' brothers. Cornelius and Steven. Joseph Barboza, a one time hit-man for the Winter Hill Gang who would in the future work for the Patriarca crime family and go on to become an FBI Informant, took on the contract along with "Cadillac Frank" Frank Salemme, a half-Irish, half-Italian Winter Hill Gang hood who would later become Godfather of the Patriarca Family. On May 26th, 1966 the two man hit team got rid of Cornelius Hughes, they shot the Charlestown mobster to death in Revere, Massachusetts. On September 23rd, 1966 Steven Hughes and another Charlestown Mob member and Sammy Lindenbaum were gunned down while driving through Middleton, Massachusetts.
In the early 1970's the Boston Irish Mob Wars were finally put to an end. Over forty members and associates from each gang were dead. With the Charlestown Mob eliminated the Winter Hill Gang became the dominant Irish gang in New England, in the end Winter Hill had too many members, associates and allies for the Charlestown Mob to handle.
In 1975, James "Whitey" Bulger, a Winter Hill Gang Soldier, who had missed out on all the murders of the Irish Gang War through serving a sentence in prison for bank robbery, was released. Bulger soon served as one of Winter's Lieutenants handling South Boston for Winter because Winter "trusted" him. Within months Bulger would begin co-operating with FBI Agent and Southie native John "Zip" Connolly. Bulger fed Connolly information which helped put his rivals away and kept him on the streets and in most cases ahead of the game in Boston's underworld activities. In 1979 Winter's reign as Boss would end when information gathered by Bulger and Stephen Flemmi and forwarded on to agent Connolly placed many members and associates of the Winter Hill Gang under indictment on charges of money laundering, income tax evasion and horse race fixing.
As a result Winter was sent to federal prison. He was released from prison in 1987. In 1993, he was caught dealing cocaine. When the FBI informed him that Whitey had been a snitch all those years and offered Winter a deal if he would inform on Bulger, Winter refused the deal telling the FBI he was no "rat", despite facing another decade behind bars, which he would serve, being released from prison in July 2002.
In 2012, the 83-year-old former powerful head of the Winter Hill Gang was arrested on charges of attempted extortion and conspiracy.
Winter and an accomplice repeatedly met with the victims at the Sons of Italy club in Medford and allegedly demanded that they each pay Winter $35,000. His trial on the extortion charges is currently pending as of February 2014.