Boston man just released from a seven-year prison sentence charged with armed robbery, held without bail pending dangerousness hearing

BOSTON, February 27, 2025 – A Boston man who just finished serving a seven-year prison sentence for armed robbery this month was arraigned Wednesday in BMC Central on a new armed robbery charge after police link him to two recent bank robberies, Suffolk County District Attorney Kevin Hayden announced.

JEREMY WOODLEY, 44, was charged with one count of armed robbery. Judge James Stanton ordered Woodley held without bail pending a dangerousness hearing on March 3.

At about 9:59 a.m. on February 20, police responded to the Berkshire Bank located at 1320 Washington Street for a robbery. The teller reported that an unknown male, later identified as Woodley, entered the bank and handed the teller a note stating “I have a gun, comply with my demand. No one will be hurt. I want all loose bills. 100s, 50s and 20s, no dye packs or tracers.” The teller handed Woodley $500 in U.S. currency. Woodley fled on foot onto Washington Street toward Union Park.

Officers were later notified by the owner of Empire Loans located nearby at 1130 Washington Street that Woodley had entered his business and asked to use a pen. Woodley used the pen to write something on a piece of paper before heading in the direction of Berkshire Bank.

At about 9:36 a.m. on February 21, police responded to a robbery at Citizens Bank located at 580 Washington Street in Boston. The teller reported that Woodley slid a note to her stating a similar demand from the previous day. The teller handed Woodley $500 in U.S. currency and he fled down Washington Street toward Kneeland Street.

Investigators used video surveillance from nearby businesses and MBTA stations to identify Woodley. Woodley is seen counting money on video. Woodley was located and arrested on Tuesday in the area of Dalkeith Street and Howard Avenue in Dorchester by members of the FBI’s Violent Crimes Task Force and Boston police.

Charges in relation to the Berkshire Bank robbery on February 20 will be issued at a later date.

Woodley has been convicted of multiple armed robberies. In 2010, Woodley was sentenced to a six-year state prison sentence. In 2017, Woodley was sentenced to a seven-year prison sentence out of Suffolk Superior Court and was released earlier this month.

“Technology, witness descriptions and solid police work came together here in the arrest of a person who just finished a lengthy prison term and may now be looking at yet another one,” Hayden said.

All charged individuals are presumed innocent until and unless proven guilty beyond a reasonable doubt.

Suffolk County District Attorney Kevin Hayden’s office serves the communities of Boston, Chelsea, Revere, and Winthrop, Mass. The office handles over 20,000 cases a year. More than 160 attorneys in the office practice in nine district and municipal courts, Suffolk Superior Court, the Massachusetts Appeals Court, the Supreme Judicial Court, and the Boston Juvenile Courts. The office employs some 300 people and offers a wide range of services and programs to serve anyone who comes in contact with the criminal justice system. This office is committed to educating the public about the services we provide, our commitment to crime prevention, and our dedication to keeping the residents of Suffolk County safe.

James Borghesani, Chief of Communications