Middletown Bandit Matthew Dragoone Sentenced for Bank Robbery Spree

The grim saga of Middletown’s bank-robbing bandit Matthew Dragoone took a decisive turn as the 32-year-old was sentenced to six years in federal prison. United States Attorney Deirdre M. Daly announced yesterday’s sentence for Dragoone, who pleaded guilty to robbing six banks and attempting another in 2015.

Dragoone’s spree began on August 12, 2015, with the Webster Bank in Cheshire, followed by hits at TD Bank and Liberty Bank locations across Connecticut. His distinctive modus operandi involved wearing a baseball cap and dark sunglasses while holding a cellphone to his ear, presenting bank-style bags with notes demanding cash.

Court documents revealed that Dragoone’s house yielded clothing and sunglasses matching those used in the Durham robbery, as well as a bank-style bag identical to the ones he used. The law enforcement team, including the FBI and Connecticut State Police, along with local departments, tracked down Dragoone on September 18, 2015.

After his arrest, Dragoone was charged and pleaded guilty to one count of bank robbery in February 2016. Assistant U.S. Attorney Douglas P. Morabito prosecuted the case, which received significant assistance from the Connecticut Department of Emergency Services and Public Protection’s Division of Scientific Services.

The sentencing, handed down by U.S. District Judge Janet Bond Arterton in New Haven, includes a term of three years of supervised release following the prison sentence. Dragoone will now have to face the consequences of his criminal activities that terrorized several Connecticut communities.