Chester Official Convicted of Shooting Delivery Driver Outside His Home

MIDDLETOWN, N.Y.—Town of Chester resident and Highway Superintendent John Reilly on March 26 was convicted on four felony charges after shooting a delivery driver outside his house in 2025.

Jurors found Reilly, 49, guilty of first and second degree assault, both violent felonies, Orange County District Attorney David Hoovler said in a news release. Reilly was also convicted of two weapons possession charges.

Reilly was sent to the Orange County jail and will be sentenced on May 18.

Documents allege that on the night of May 2, 2025, a lost and unarmed DoorDash delivery driver approached Reilly’s house in Chester with a bag of food. The delivery man’s phone had run out of battery, and he approached the house, asking whether Reilly had ordered the food. Reilly told the delivery driver to leave.

As the driver was leaving in his vehicle, Reilly came out of his house with a shoulder holster carrying a .45-caliber Glock pistol. Reilly shot the gun into the front lawn. As the car was driving away, he shot at the vehicle. A few seconds later, Reilly aimed at the car again and shot, and the round pierced the vehicle and hit the driver in the lower back.

The projectile was recovered from the victim’s abdomen during an emergency surgery, which required removing two feet of the driver’s small intestine. The driver survived and is recovering, Hoovler said.

A search warrant was issued, and Reilly’s residence was searched, which resulted in the recovery of .45-caliber casings in the kitchen and front lawn, a shoulder holster, a loaded .45-caliber Glock pistol, and seven other illegally possessed pistols.

Reilly held a federal firearms license, which allows individuals to sell firearms, but he didn’t have a New York State firearms license or pistol permit and therefore illegally held the guns.

Chester Supervisor Brandon Holdridge told The Epoch Times on March 27 that Reilly was dismissed as highway superintendent as soon as he was convicted, as per New York state law.

Holdridge said the Town Board has put out a notice for residents in Chester to be interviewed for the position. The chosen candidate will serve as the interim highway superintendent until the next election to fill the job.

Hoovler thanked the New York State Police, whose investigation led to the arrest. He also acknowledged the assistance of the Bureau of Alcohol, Tobacco, Firearms, and Explosives.

“This defendant’s depraved indifference to human life was appalling and nearly resulted in the death of an innocent man,” Hoovler said in a statement.