Lost DoorDash Driver Shot by Town Official in Upstate NY — Chester Highway Superintendent Arrested in Shocking Attack
CHESTER, N.Y. (May 7, 2025) — A small town in upstate New York is reeling after a shocking act of violence involving a local government official. John Reilly, the highway superintendent for the Town of Chester — located about 60 miles north of Manhattan — was arrested over the weekend for allegedly shooting a DoorDash delivery driver who had approached his home seeking directions.
According to a statement released by the New York State Police, the incident occurred on the evening of Friday, May 2, when the delivery driver became disoriented while trying to complete an order in Reilly’s neighborhood. The driver, who has not yet been publicly identified, was reportedly struggling to navigate using the DoorDash app and stopped at several homes in the area to ask for help.
When the driver arrived at Reilly’s residence, police say the situation quickly escalated.
“Reilly told the victim to get off his property, before firing multiple shots at the victim as he attempted to leave in his vehicle, striking the victim once in the back, causing serious physical injuries,” state police stated in a release.
Reilly, 48, who is also a federally licensed firearms dealer, has been charged with first-degree assault and criminal possession of a firearm. He was taken into custody and remanded to the Orange County Jail, where he is being held on $250,000 cash bail, $500,000 bond, or $750,000 partially secured bond. A preliminary court hearing is scheduled for May 9 in the Town of Chester Court.
Authorities have not yet confirmed the condition or identity of the victim, though it is believed the injuries are severe. The shooting has drawn condemnation and concern from both local officials and the public.
Community Leaders Respond
Chester Town Supervisor Brandon Holdridge addressed the incident in a public Facebook post, stating that both he and the town board were “deeply troubled” by the allegations against Reilly.
“We are horrified by what has taken place and are praying for the delivery driver’s full and healthy recovery,” Holdridge wrote. However, he also noted a significant complication in the matter: “As an elected official, Mr. Reilly cannot be dismissed or suspended by the town government unless he is convicted or resigns. This process is not within our control.”
Holdridge also confirmed that the Chester Police Department had recused itself from the investigation due to the suspect’s role in local government. The case is now being handled solely by the New York State Police and the Orange County District Attorney’s Office, although the DA’s office has not yet issued an official comment.
DoorDash: “Devastated by This Senseless Act”
In a statement sent via email, DoorDash expressed outrage and sorrow over the incident.
“We are devastated by this senseless act of violence,” a company spokesperson wrote. “No one should ever fear for their safety just for trying to make deliveries in their neighborhood. Our thoughts are with the driver and their loved ones. We are committed to supporting them and will continue to work closely with law enforcement as they investigate this tragic incident.”
The statement also emphasized that DoorDash is reviewing the events that led up to the shooting and evaluating safety measures in the area.
A Town Shaken
The shooting has sparked outrage and fear in Chester, a quiet Hudson Valley town not accustomed to this level of violence — especially not involving a prominent elected figure. Residents have taken to social media and local forums to express their shock, many calling for Reilly to resign and for stronger accountability in public office.
“This could’ve been any one of us — a lost delivery driver, a mail carrier, a neighbor,” said longtime Chester resident Lillian Gonzalez. “It’s horrifying to think someone could be shot just for asking directions.”
As of Tuesday evening, Reilly had not made a public statement, and attempts to reach him or his legal representation were unsuccessful. His office phone has gone unanswered, and it is unclear whether he has retained an attorney.
More details are expected to emerge as the case proceeds to court later this week. The town remains on edge as both the legal and political consequences of the shooting unfold.
Check back for updates following the May 9 preliminary hearing.