Jeremy D. Woodley Pleads Guilty to Boston Bank Robberies

Boston is breathing easier with Jeremy D. Woodley, 38, admitting his role in a string of armed bank heists that terrorized tellers across the city. Woodley pleaded guilty in U.S. District Court to three counts of bank robbery, setting the stage for a sentencing date on April 5, 2017, before Judge Leo T. Sorokin.

The crime spree began on May 5, 2016, when Woodley walked into a Santander Bank branch in Boston, slapped down a demand note claiming he was armed, and walked out with $599. Just days later, on May 17, he struck again—same bank, same script—this time stealing $927 from another Santander location. The pattern confirmed: a cold, methodical thief working a tight schedule.

But Woodley pushed his luck too far on May 21, 2016, when he robbed a Commerce Bank branch in Boston, grabbing $1,995 in cash. Witnesses saw him flee on foot, duck into the back seat of a waiting vehicle. That detail sealed his fate. Law enforcement picked up the trail fast, initiated a brief chase, and arrested Woodley—still clutching the stolen money from Commerce Bank.

Federal prosecutors wasted no time building the case. Each count of bank robbery carries a maximum penalty of 20 years in prison, three years of supervised release, and a $250,000 fine. While actual sentences often fall below the cap, the toll of repeated armed robberies weighs heavy under federal sentencing guidelines.

The takedown was a joint effort. United States Attorney Carmen M. Ortiz, FBI Special Agent in Charge Harold H. Shaw, and Boston Police Commissioner William Evans all confirmed the arrest and guilty plea. The case is being prosecuted by Assistant U.S. Attorney Kenneth G. Shine, part of Ortiz’s Major Crimes Unit, known for hammering down on violent street offenses.

Woodley’s crime spree lasted just over two weeks. His downfall came swift. With cash in hand and witnesses talking, there was no hiding from federal time. Now, all eyes turn to April 5—when Judge Sorokin decides just how many years Jeremy D. Woodley will spend behind bars.