The Biggest Bank Robbery In Massachusetts History

Movies about bank heists are rampant. "The Town", "Heat", and "Point Break" are just a few that come to mind. What was Massachusetts' biggest bank robbery?

There was a big arrest made in Milford, MA where a 51 year-old man rented a car drove to Pittsfield, MA and robbed an NBT Bank to the tune of $150,000.

Christopher Oliveri was arrested at 5:30 a.m. on Wednesday morning in Milford and is being held. This was a professional job where he zip tied employees, was disguised and implored employees not to call authorities until 10 minutes after he left. He robbed the bank just before they were set to close around 5:00 p.m. on Nov. 29, 2023.

The Pittsfield robbery was nothing compared to the commonwealth's biggest ever bank robbery.

The Biggest Bank Heist in Massachusetts History.

On the evening of January 17, 1950, employees of the security firm Brinks, Inc., in Boston, Massachusetts, were closing for the day, returning sacks of undelivered cash, checks, and other material to the company safe on the second floor.

Shortly before 7:30 p.m., they were surprised by five men—heavily disguised, quiet as mice, wearing gloves to avoid leaving fingerprints and soft shoes to muffle noise. The thieves quickly bound the employees and began hauling away the loot.

Within minutes, they’d stolen more than $1.2 million in cash and another $1.5 million in checks and other securities, making it the largest robbery in the U.S. at the time. -fbi.gov

A captain marvel mask used in the robbery, photo credit to fbi.gov.

This was once considered the perfect crime, however, by 1956 all arrests were made.