New York Town Official Arrested for Shooting Lost DoorDash Driver, Police Say
- 17GEN4
- May 6
- 3 min read
CHESTER, N.Y. — A town official in upstate New York was arrested Saturday after allegedly shooting a DoorDash delivery driver who, lost and seeking directions, approached his home on Friday night, according to the New York State Police.

John J. Reilly III, 48, the highway superintendent for the Town of Chester, approximately 60 miles north of Manhattan, faces charges of first-degree assault, second-degree criminal possession of a weapon, and criminal possession of a firearm, all felonies. The incident occurred around 9:50 p.m. on May 2 at Reilly’s residence on Valerie Drive, a quiet neighborhood in Orange County.
Police reports state that the 24-year-old DoorDash driver, whose identity has not been publicly disclosed, was attempting to deliver food but became disoriented, unable to navigate using the DoorDash app. Family members told local media that the driver, a recent immigrant from West Africa residing in nearby Middletown, was unfamiliar with the area, spoke limited English, and had a dead phone battery, complicating his efforts to find the correct address.
After knocking on several neighbors’ doors to ask for directions, the driver arrived at Reilly’s home. Authorities say Reilly, a federally licensed firearms dealer, ordered the driver to leave his property. As the driver returned to his vehicle and attempted to drive away, Reilly allegedly fired multiple shots, striking the driver once in the back. The bullet caused serious, potentially life-altering injuries, though the victim was reported to be in stable condition as of Tuesday, police said.
“There’s nothing to indicate the victim had any nefarious intentions,” New York State Police Capt. Joseph Kolek told reporters. “He’s just out there doing his job, trying to make a food delivery.”
The driver, unaware he had done anything wrong, drove himself home before seeking medical attention at Garnet Health Medical Center, where staff alerted authorities to the gunshot wound, prompting the state police investigation. The Chester Police Department recused itself from the case due to Reilly’s position as an elected town official.
Reilly was arraigned at the Orange County Centralized Arraignment Part and is being held at Orange County Jail on $250,000 cash bail, $500,000 bond, or $750,000 partially secured bond. A preliminary hearing is scheduled for Friday morning in the Town of Chester Court.
Chester Town Supervisor Brandon Holdridge issued a statement on social media, expressing dismay over the incident. “We are deeply troubled by what has been reported so far,” Holdridge wrote, wishing the injured driver “a full and healthy recovery.” He clarified that the town board has no authority over Reilly’s position, as the highway superintendent is an elected role, and emphasized that the investigation is being handled by state police to ensure impartiality.
DoorDash, in a statement to the press, condemned the shooting as a “senseless act of violence.” “No one should ever fear for their safety just for trying to make deliveries in their neighborhood,” a company spokesperson said. “We’re devastated and wishing the Dasher a full and speedy recovery. We’ll continue to work closely with law enforcement as they investigate this tragic incident.”
The shooting has drawn comparisons to other recent incidents in which individuals were attacked after approaching the wrong property, including the 2023 fatal shooting of 20-year-old Kaylin Gillis in upstate New York, killed when her car mistakenly entered a homeowner’s driveway. The Chester incident has reignited discussions about gun violence and the safety of gig economy workers, particularly those navigating unfamiliar areas at night.
The investigation remains ongoing, with the New York State Police collaborating with the Orange County District Attorney’s Office and the Bureau of Alcohol, Tobacco, Firearms and Explosives. Authorities have not released additional details about Reilly’s motive or the circumstances leading up to the shooting.
Sources: New York State Police, ABC News, The New York Times, The Guardian
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