Boston Gang Wars- Loan Sharks and Bookies: Harold “Zimmy” Zimmerman

HAROLD “ZIMMY” ZIMMERMAN, 38                        November 8, 1956

Zimmerman would be the first of three Jewish men involved in the bookmaking business who were murdered between 1956 and Labor Day, 1961. The North End sought to send a message to the Jewish bookmakers that dealing in the same business as the North End could be quite deadly. The message was clear. The response had to be equally clear.

Boston was different than New York City.  In New York City, the Jewish gangsters made up a big part of the muscle and killers in Murder Inc.  But, this was Boston.  Members of the Jewish bookmaking operations in Boston, for the most part, avoided violence. They recognized their business was all about making money and they knew the Mafia had the same interest. In Boston, Jewish gangsters had gotten gains by paying periodic agreed-upon tribute to them. The Jewish bookmakers knew by paying tribute, they would not only be left alone but, as an added benefit, they would be protected because they were now money makers for the Mafia. Paying tribute meant no issue mixing it up in gun fights and would have likely distributed one-to-one retribution.

It took some time for Jewish bookmakers in Boston to embrace the idea of cutting the North End Mafia in on their take by paying tribute.  The Jewish bookmakers initially had no plans to cut anyone in on their profits. Like any gangsters, they wanted to keep all the money they earned. But they slowly changed as they watched what happened to people who likewise felt they should keep all their profits.

Morris “Whitey” Hurwitz, an ex-West End boxer, a bookie and a tough strong-arm man was murdered in January 1953.  But then, Harold Zimmerman was murdered.  Prior to Harold Zimmerman’s murder, Hurwitz’s murder did not raise much concern among Jewish bookmakers.

Hurwitz’s murder was, according to a Boston Glove article, “the first gangland slaying in Greater Boston since another bookie-gambler, George Killeen of South Boston was shot down on Hanover Street, North End, three years ago.” Hurwitz was believed to have been holding up protected dice games.

Live by the gun die by the gun. Hurwitz was walking to his house when he went over to a car idling nearby. He stuck his head in the window and two .38 caliber bullets were fired into his head.  “Specs” O’Keefe ,when an inmate on death row at Sing Sing, said Elmer “Trigger” Burke murdered Hurwitz.

Zimmerman was found dead in his parked car on the Fenway at the rear of the Museum  of Fine Arts. He had someone in his car sitting next to him who fired two bullets into his face and one into his lung from inches away. He fell over from the driver’s seat onto the passenger seat on top of three spent shell. He had been lying there for a day or two before he was discovered by a police officer at 2:25 a.m. He was described as single and a Navy veteran.

Police found three diaries that belonged to Zimmerman with addresses and telephone numbers. Hurwitz’s name was in the diaries. The discovery of Hurwitz’s name would be expected since he and Zimmerman were in the same business. The names of over 200 women were also in the diaries.  The women’s names caused the police to theorize that a woman did the murder.  Witnesses said he was seen parked at that spot the night he was slain talking with a woman. This important clue caused the police to look for a jealous woman as the gun person.

The police also had information that Zimmerman had welshed on some heavy bets. An impoverished gambler, his personal effects and bank accounts showed that he had suffered recent heavy gambling losses.  The police also learned that he was being dunned by those who he owed money. Zimmerman had been threatened by someone shortly before his death.

At one point, the police considered a man who was incensed over the attention Zimmerman was paying to his girlfriend as a suspect. Zimmerman apparently had lots of women friends. Many woman were questioned,  but nothing came of it.

It would be highly unusual for a woman to fire a .38 caliber gun point blank in a man’s face because of jealousy, though it cannot be ruled out that a woman did the hit. The most likely explanation for his murder is Zimmy, a bookie, was not paying off his debts probably owing big money to the North End and was considered a dead beat.

Zimmerman parked on the Fenway waiting for someone. The person he let into his car was probably who he planned to meet. Whoever came looking for money, he got only promises, and so he killed him; or came with the intent of eliminating him as a threat to the organization. Rumors had circulated that he was cooperating with or would be called by a federal grand jury

Could the person who murdered him have been a woman? Perhaps. Although women do not usually do hired hits. We saw the movie, The Sting, had a hit woman. Boston may have had one hit woman named Barchard but she would have been too young to do Zimmerman. But one thing seems certain, the way the meet was set up seems to eliminate it being a spurned lover.

Zimmerman owed money. He was broke and out of choices. He was being threatened. He was rumored to be cooperating. When mixed together, this is usually the recipe that spells murder at the hands of the North End gangsters.  A couple subsequent murders point the Zimmerman murder in the same direction.


  1. neal e connolly

    Very interesting

  2. Another great article about some of the lesser known figures
    in the Boston underworld. Great stuff.