Winter Hill Gang Murders- MICHAEL MILANO, 23

March 9, 1973-

Jerry Angiulo must have had his doubts about engaging the Winter Hill gang after he heard about the murder of Michael Milano.  Winter Hill had hit the wrong guy.  Winter Hill’s capabilities were mostly unknown. John Martorano had killed lots of people, so he certainly knew how to shoot a gun. But Martorano’s murders primarily consisted of attacks on people he knew or had befriended and often he snuck up behind them and shot them in the head. Would he be capable of murdering strangers who were gangsters?

Michael Milano

Howie Winter had not been pegged as a murderer at the time. One of their associates, Jimmy Sims, was believed to have been with Joe McDonald when he murdered a witness but had no other known association with murders. They made plans that would involve Jimmy Sims driving the car. Winter and Martorano was passengers would have automatic firing weapons called grease guns, crude versions of the AR-15s or AK-47s of today but capable enough of murdering someone.

Their target was Al Angeli. He was supposed to hang around a place in which he had an ownership interest called Mother’s in the North End near North Station and the Boston Garden, the home of the Celtics and Bruins.

John Martorano

Martorano claims he enlisted Whitey Bulger as a part of the hit team to supposedly drive another car.  I always thought Whitey’s involvement was just a throw in by Martorano.  I do not believe Whitey was there. He too had just joined Winter Hill in 1972 but had no relationship with the Mafia. Nor had he murdered anyone at this point in his career. At Whitey Bulger’s trial, the Boston jury hearing evidence presented by the prosecutor also agreed it was not proven rejecting the testimony of Martorano.

One of the Winter Hill associates went into Mother’s, according to Martorano, to put a peek on Angeli. Their guy mistakenly thought Michael Milano was Angeli. He called the information back to the hit team.

Milano left Mother’s with a woman named Dianne Sussman and her boyfriend Louis Lapian. He drove the same model car as Angeli having bought the car six days earlier, Milano insisted that Dianne sit in the front passenger seat because he wanted her to see the gadgets and enjoy the ride. Louis was in the back seat. Louis and Milano, recent but avid chess players, jocularly discussed their chess skills.

They stopped at a light at the intersection of Market Street and Sparhawk Street in Brighton, right next to St. Columbkille’s convent. Martorano’s vehicle pulled up beside them. He and Winter opened fire. They fired twenty or more rounds into the car.

Milano a twenty-three-year-old well-liked guy who grew up in Winthrop was murdered. He played football in high school and was a CYO boxing champion. His uncle said he loved life. The day before his death he spoke with his uncle about opening his own lounge somewhere in the city.

Louis Lapian was severely wounded. He spent the remainder of his life paralyzed from the neck down. Dianne came out physically unscathed. It haunted her that she would have normally been sitting in the back seat where her boyfriend Louis sat except for Milano’s insistence.

Diane testified at the trial of Whitey Bulger. Her testimony of the night of Milano’s murder and her subsequent relationship with Louis brought tears to everyone’s eyes. She married, had children, but always remained in touch with Louis helping him through his darkest days on a respirator. She stayed loyal to Louis over the next 21 years telling how her kids interacted with him and how her deal on marrying her husband was that Louis would remain part of her life.

I will never forget the beautiful smile that lit up her face when she was shown the photograph of Michael Milano. It seemed to bring forth happy memories as if she were back to the time before he was murdered. Back to the time she watched as he and Louis joke around and play chess together, reflecting her fondness for him and the joys of youth.  Her smile and nostalgia vividly brought home the great evilness of taking a life.

In recounting these gangland murders, one can never forget the reverberating effect each murder has on the victim’s children, their loved ones, and other people in their lives. No man is an island. The murder of one will cause great suffering among many others. When Dianne testified, one juror would later say she felt revulsion toward the government thinking that it made a deal with Martorano to do only twelve years in prison for his dozens of murders. She watched Martorano testify as if his murders were no different than knocking over candle pins at a bowling alley.  She remarked that Martorano did not show the slightest bit of remorse.

The investigation into the Milano murder confused the police. They knew it was clearly a gangland hit. Boston Police Homicide Detective James MacDonald said, “We just don’t have any evidence to indicate that Milano was the intended victim. Everyone loved the guy.” Another detective said: “Gunmen used to take some pride in the way they carried out their executions. They always hit the right man. Now they come in with powerful automatic weapons and shoot anyone, anytime, anywhere.” Howie Winter would never be prosecuted for his role in the murder because the federal prosecutors, as part of their deal with Martorano, allowed Martorano to not have to testify against Winter.

2 thoughts on “Winter Hill Gang Murders- MICHAEL MILANO, 23

  1. How corrupt are the Feds? They let Martorano hide the killings of his friends. When you take an oath to tell the whole truth you can’t hide part of it. The judge should have refused to let Martorano testify unless he told the whole truth. When he was sworn in as a witness he was violating his oath. The DOJ, FBI, DEA and Customs all broke the law when they allowed a witness to tell only part of the story. Hiding facts from the jury is a conspiracy to commit perjury by omission. Abolish the FBI, CIA and NATO.

  2. The juror was spot on. The Federal government is to be reviled for some of the plea deals they entered into.
    They are more interested in their scorecard, I wonder if Lapian was ever compensated for his tragic

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