HOWIE WINTER
 |
 |
 |
 |
Howie Winter was born in 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 "Sal" Sperlinga, Americo "Rico" Sacramone, Anthony "Tony Blue" D'Agostino, Thomas Ballou Jr., Joseph "Joe Mac" McDonald, Russel Nicholson, Ruaraidh "the Irish Godfather" Fitzpatrick and James "Spike" O'Toole.
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 McLaughlin Brothers who headed the Charlestown Irish Mob were able to eliminate Winter Hill Gang Boss James "Buddy" McLean from the picture 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 leader of the Charlestown Gang Edward "Punchy" McLaughlin had survived many assassination attempts by different members of the Winter Hill Gang on 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, Howie Winter ordered the murders of the Hughes' brothers. Cornelius and Steven, both had to go ordered Winter. Joseph "the Animal" 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 F.B.I. Informant, took on the contract along with Francis "Cadillac 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 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. The Winter Hill Gang became the dominant force, in the end they had too many members, associates and firepower for the Charlestown Mob to be able to defeat.
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 Winter's Lieutenant because Winter "trusted" him. Within months Bulger would begin co-operating with F.B.I. Agent and Southie native John "Zip" Connolly, Jr 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 Flemmi and forwarded on to agent Connolly place many members and associates of the Winter Hill Gang would on indictment on charges of money laundering, income tax evasion and horse race fixing.
As a result Winter went to prison, but in the late 1980s he would be released and then re-indicted on a narcotics trafficking indictment, again Whitey Bulger had fed Connolly information. Bulger would now take over the reigns, was boss of the Winter Hill Gang from 1979-1995.