Massachusetts extortion is an interesting white collar crime. I find that it is largely misunderstood as well.

Take the tale of Howie Winter, 83 years of age and hereinafter referred to as “Defendant1”. Defendant1 is also reputed with being the former head of the notorious Winter Hill Gang. He was just released on $25,000 bail in Somerville District Court. He is charged with trying to extort money from two people. He is accompanied by James Melvin, 70, of Braintree (hereinafter, “Defendant2”). The two are also charged with attempted extortion and conspiracy to commit extortion.

Both gentlemen have also been ordered to where GPS monitoring bracelets.

Prosecutors say the defendants tried to extort $35,000 apiece from two men, repeatedly threatening them during a series of meetings, phone calls, and voicemails. Part of this threatening was allegedly making repeated references to the North End, invoking the shadowy powers of organized crime.

Apparently, said threatening behavior was not overly successful. It merely drove the alleged victims to the hands of law enforcement.

The defendants’ attorneys describe a bit of a different scenario. They suggest that their clients were acting to aid a lawyer who was himself being extorted by the two men that the government is now portraying as the victims.

One of the attorneys asks the question of whether it is extortion to extort money from extortionists. That seems reminiscent of our present policy of bullying kids who are bullies…and we have statutory sanction for that!

But I digress.

Apparently, the government has collected recordings of the defendants in this case. The government expects those tapes to help the prosecution. The defense attorneys, however, claim that said recordings “may very well prove that there was no criminal intent.”

Attorney Sam’s Take On Extortion And Attempted Extortion

The Massachusetts General Laws defines extortion, or attempted extortion, as follows and provides for the following criminal sentence:

Whoever, verbally or by a written or printed communication, maliciously threatens to accuse another of a crime or offence, or by a verbal or written or printed communication maliciously threatens an injury to the person or property of another, or any police officer or person having the powers of a police officer, or any officer, or employee of any licensing authority who verbally or by written or printed communication maliciously and unlawfully uses or threatens to use against another the power or authority vested in him, with intent thereby to extort money or any pecuniary advantage, or with intent to compel any person to do any act against his will, shall be punished by imprisonment in the state prison for not more than fifteen years, or in the house of correction for not more than two and one half years, or by a fine of not more than five thousand dollars, or both.

The government may well have been drawn to this matter because of the defendants’ criminal past. Particularly in the era of prosecuting Whitey Bulger, folks with alleged mob ties and crimes in the past are welcome defendants. However, the question persists as to how relevant is the intent behind the extortion.

The answer might surprise you.

Nicky Needy is down on his luck. His house is about to be taken away from the bank, his kid wants to get married and his wife is sick. Poor Nicky has not worked for the past two years since he was laid off. So, he turns to his old pal Michael Money. He begs his old pal to loan him thousands of dollars to dig him out of this hole.

Reluctantly, Michael lends him the money. The two agree on a payment plan.

Time goes by and the payments do not come. Michael starts calling Nicky on the phone. Nicky is suddenly very hard to reach.

Finally, Michael starts leaving voice mail messages explaining that he is getting angry about being “blown off” and he wants his money. Now. Or else, “there is going to be trouble.”

No response.

Michael sends a letter to Nicky indicating that his patience is at an end and he is going to show up at Nicky’s house and tell his wife what a loser her husband is. In fact, he might tell the new bride (daughter) as well.

Nicky calls Michael, begs him not to go to the family and agrees to meet Michael at a different time and place.

Michael agrees. Nicky does not show.

This goes on for months. Michael gets angrier and angrier, now leaving voicemails that, unless he gets his money, he is going to “clock” Nicky.

Finally, Michael shows up at the door of Nicky’s home and is able to confront Nicky. Nicky tells him to leave him alone. Michael punches Nicky in the mouth and walks away.

Now, you do not need to be a Boston criminal lawyer to know that Michael has committed a few crimes. The most obvious one is assault and battery.

Even if you are legitimately angry…even enraged…you do not have the right to hit someone.

But what about extortion?

“Well, if the money was a legitimate debt, Michael can certainly keep pressuring Nicky and, perhaps, even threaten him. He may even be entitled to punch him.”

That is what many people believe…and they are wrong. The money at issue does not need to be part of an illegal scheme. While one can push it to some extent and be a bit nasty, one cannot threaten physical harm or perform it to pressure someone to pay them back. The remedy may be to claim a theft. The more appropriate remedy, actually, is a civil law suit.

Remember, to threaten someone with physical harm is not only extortion under this scenario, but it is a crime in itself. It would be a crime to cause the physical harm. Therefore, it is a crime to threaten to do so. The charge is “threats to commit a crime”.

To read the story upon which this blog was based, please go to

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