The Five Most Notorious Boston Bank Robbers: From The 1950 Brink's Heist To 2025's Serial Arrests

Boston’s criminal history is inextricably linked to its notorious bank heists, a legacy that stretches from the mid-20th century's "perfect crime" to the swift, high-tech arrests of today. As of late 2024 and early 2025, the FBI Boston Division and the Boston Police Department (BPD) continue to actively pursue and charge individuals involved in serial bank robberies, demonstrating that the allure of a quick cash grab, whether armed or unarmed, remains a persistent problem in the Greater Boston area.

This article dives deep into the most significant and recent cases, spotlighting the individuals who have made headlines, the methods they used, and the aggressive law enforcement response, particularly from the joint task forces working to keep the city’s financial institutions secure. The landscape of bank crime is shifting, but the commitment of the authorities to capturing these perpetrators has never been stronger.

Recent Arrests and High-Profile Cases (2024–2025)

The narrative of the "Boston bank robber" is constantly being updated, and the most current data from the FBI and local police show a focused effort to dismantle serial operations. The following individuals represent some of the most significant arrests and pleas in the Boston area from late 2024 through the current date of December 15, 2025.

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1. Jeremy Woodley: The February 2025 Serial Suspect

Biography & Profile:

• Name: Jeremy Woodley
• Age: 44
• Residence: Boston, Massachusetts
• Charges: Suspect in two recent bank robberies.
• Arrest Date: Tuesday, February 25, 2025.
• Location of Crimes: Multiple banks in the Boston area.

Woodley’s arrest in February 2025 highlights the immediate response capabilities of the Boston Police Department. Following a coordinated investigation, officers and detectives successfully apprehended Woodley in connection with two recent bank robberies. The rapid identification and arrest of suspects like Woodley are crucial in disrupting the pattern of serial bank crime that often plagues metropolitan areas.

2. Glenn Legere: The December 2024 Santander Robber

Biography & Profile:

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• Name: Glenn Legere
• Age: 46
• Residence: Quincy, Massachusetts
• Charges: Armed robbery of a bank.
• Crime Date: December 2024.
• Location of Crime: Santander Bank in Weymouth, MA.
• Status: Pleaded guilty in federal court.

Glenn Legere’s case is a prime example of a perpetrator facing federal charges for armed robbery. He pleaded guilty in federal court in Boston in connection with the December 2024 armed robbery of a Santander Bank located in Weymouth. The involvement of federal prosecutors underscores the severity of armed bank robbery charges, which often result in lengthy prison sentences and supervised release.

3. The Unnamed Chelsea Serial Bank Robber

Biography & Profile:

• Name: Unnamed Chelsea Man (as of press release)
• Residence: Chelsea, Massachusetts
• Charges: Armed robberies of three local banks.
• Crime Date: 2024.
• Location of Crimes: Banks in Weymouth, Jamaica Plain, and Hyde Park.
• Status: Pleaded guilty in federal court.

In a separate federal case, a Chelsea man pleaded guilty to the armed robberies of three different banks across the Greater Boston region in 2024: one in Weymouth, one in Jamaica Plain, and one in Hyde Park. This individual was part of a disturbing trend of serial bank robbers who target multiple locations over a short period. His guilty plea is a victory for the FBI Boston Division and the local police departments that collaborated on the investigation.

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The Historical Context: Boston's Most Infamous Heist

To understand modern bank crime in Boston, one must look back at the case that defined the genre: The Great Brink's Robbery. This historical context provides essential topical authority on the city's criminal history, shifting the focus from individual robbers to organized crime.

4. The Great Brink's Robbery (1950)

Overview & Profile:

• Mastermind: Anthony Pino (Career Criminal).
• Key Accomplice: Joseph "Specs" O'Keefe (later turned informant).
• Other Robbers: Stanley Gusciora, Henry Baker, Adolph “Jazz” Maffie, and others (a total of 11 men).
• Date: January 17, 1950.
• Location: Brink's building on Prince Street in the North End of Boston.
• Loot: Approximately $2.7 million (the largest robbery in U.S. history at the time).

The Great Brink's Robbery, often called "The Perfect Plan," was a masterpiece of organized crime. On the evening of January 17, 1950, a crew of 11 men, led by mastermind Anthony Pino, entered the Brink's security company building in Boston's North End. The robbers, wearing duplicate uniforms and Halloween masks, knew the building's layout and safe combinations, allowing them to escape with approximately $2.7 million in cash and securities—a staggering sum for the time.

The case baffled investigators for years, becoming one of the most infamous bank heists in American history. The breakthrough only came in 1956 when one of the crew members, Joseph "Specs" O'Keefe, became an informant, leading to the eventual indictment of the other members. This event cemented Boston’s reputation in the annals of major American criminal history.

The Modern Fight Against Bank Crime

Today, bank robbery is less about a massive, organized "money heist" and more about smaller, often serial, unarmed or armed robberies driven by desperation or addiction. The response is led by specialized units focusing on rapid identification and apprehension.

The FBI Boston Violent Crimes Task Force

The primary force combating bank robbers in the region is the FBI Boston Division's Violent Crimes Task Force, working in close partnership with the Boston Police Department (BPD). This task force utilizes advanced surveillance, digital forensics, and inter-agency collaboration to track down perpetrators, regardless of whether the crime involves a gun or just a threatening note (unarmed bank robbery). The focus is on disrupting the activities of serial offenders, who are responsible for a disproportionate number of incidents.

Recent operations have led to the capture of several other notable figures, including:

• Thomas J. Flannery: Arrested by the Task Force for bank robbery charges.
• Dimitri Long ("U-30 Bandit"): Sentenced to 20 years in prison for his string of robberies, a severe penalty often given to serial bank robbers.
• The Rockland Trust Bank Suspect: A case where the Task Force and BPD actively sought information regarding a robbery at the Rockland Trust Bank on N. Harvard Street.

Evolving Trends in Boston Bank Robbery

While the total number of bank robberies nationwide has generally declined due to improved security, the Boston area still sees a consistent number of incidents. The trends observed by the FBI Boston Violent Crimes Task Force include:

1. The Rise of Unarmed Robbery: Many modern incidents are unarmed bank robberies, where the robber passes a note demanding cash, relying on intimidation rather than a visible weapon. This often leads to less severe charges but still constitutes a serious federal offense.
2. Focus on Suburbs and Outlying Areas: While major city banks are still targeted, recent cases in Weymouth, Jamaica Plain, and Hyde Park demonstrate that perpetrators are often targeting financial institutions in Greater Boston suburbs, likely perceiving them as having slightly less security or fewer police patrols.
3. The Serial Nature of Crime: A majority of the arrests, such as those of Jeremy Woodley and Glenn Legere, involve individuals who committed multiple robberies. Law enforcement focuses on quickly identifying these "serial" robbers to prevent further incidents and ensure public safety.

The high-profile arrests in 2024 and 2025 demonstrate that Boston’s law enforcement community, from the BPD to the FBI’s specialized task forces, remains highly effective at solving these cases, ensuring that the days of the "perfect crime" like the Brink's Robbery are firmly in the past.