Howie Winter, the onetime leader of the notorious Winter Hill Gang, and an alleged accomplice will be arraigned Tuesday on multiple counts of attempted extortion and conspiracy.
Winter, 83, and James Melvin, 70, are facing the charges in Middlesex Superior Court in Woburn, the Middlesex district attorney’s office said.
Beginning in February, Winter, of Millbury, and Melvin, of Braintree, participated in a months-long scheme to extort $35,000 each from two businessman, according to the office of District Attorney Gerard T. Leone Jr..
The two victims had made a series of loans to an attorney in November who then had trouble with the repayment. The men were then repeatedly threatened during phone calls, and in voicemail and in a series of meetings, Leone’s office said.
Winter and one of the victims met for the first time in February at the Sons of Italy Hall in Medford, the statement said. Winter allegedly warned that the men had engaged in a loan transaction without the consent of unidentified people in the North End, a reference the victim understood to mean organized crime in that area, according to the statement.
For several weeks after, Leone’s office said, Melvin, acting in agreement with Winter, threatened the two businessmen.
The victims soon contacted the police and audio recorded their next meeting with Winter and Melvin in March.
At that meeting, Winter and Melvin demanded a large sum of money from both men, and Winter criticized one of the victims for not knowing about his mob fame, Leone’s office said.
Melvin and Winter continued the threats, and at one point, Melvin and an unidentified man left a letter in a mailbox belonging to one of the victims that the businessmen believed was meant to intimidate him, the statement said.
State troopers audio recorded and videotaped three cash payments made by the businessmen to Winter and Melvin, which led to them demanding that the victims further pay $5,000 a month, according to the statement.
Winter and Melvin were arrested in June and each released on $25,000 bail, Leone’s office said.
Winter was last released from prison in 2002 and has been working as a property manager out of his home. Melvin has also had run-ins with the law; he was one of six men convicted in 1991 for an attempted robbery of an armored truck in Abington.Melanie Dostis can be reached at email@example.com.