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Chester highway superintendent charged with shooting lost DoorDash driver

Chester Highway Superintendent John Reilly III
Mobile Patrol
Chester Highway Superintendent John Reilly III

The highway superintendent of the Town of Chester, New York has been arrested for allegedly shooting a delivery driver who stopped by his home to ask for directions.

New York State Police say a DoorDash driver stopped by the home of Highway Superintendent John Reilly III and was shot just before 10 p.m. Friday. Police have not described nor identified the driver, other than to say he is 24 years old and grappled with a language barrier.

Joseph Kolek, a captain with the State Police Bureau of Criminal Investigation at Troop F in Middletown, says the driver got lost while trying to deliver an order on Valerie Drive. He says the driver approached multiple homes on the street for help before getting to Reilly’s residence.

“During the interaction with the victim, suspect John J. Reilly III, age 48, told the victim to get off his property before he then discharged multiple rounds from a handgun while the victim was attempting to leave the suspect’s property," Kolek tells WAMC.

Kolek says the driver was shot in the back, and stopped at a nearby Cumberland Farms to alert the clerk that he had been injured. He says the driver left before EMS personnel arrived, and a Middletown police officer was ultimately flagged down by a motorist trying to bring him to Garnet Health Medical Center in Wallkill.

Kolek says the delivery driver is now in stable condition, but with serious injuries.

"I would categorize them as life-altering,” says Kolek.

Reilly was charged with assault, criminal possession of a weapon and criminal possession of a firearm — all felonies. He was remanded to the Orange County Jail in lieu of $250,000 cash bail. An attorney for Reilly did not return a request for comment from WAMC Monday.

The shooting sounds similar to a pair of cases from 2023. Just days after Ralph Yarl, a Black teenager, was shot twice after ringing the wrong doorbell in Kansas City, Missouri, 20-year-old Kaylin Gillis was shot and killed by a Hebron, New York homeowner after mistakenly pulling up the wrong driveway with her friends. The cases reignited scrutiny of self-defense laws nationwide, including “stand your ground” statutes in some states, and whether they contribute to an increase in gun violence.

Peter Joy, a law professor at Washington University in St. Louis, told NPR at the time that “stand your ground” statutes create confusion for police and the public alike.

“It’s clouded up everything and has led to the misconception that if somebody rings your doorbell, maybe jiggles your door, that you are permitted to go ahead and harm them physically," said Joy.

New York’s self-defense law does not include a “stand your ground” statue, but it does have a “castle doctrine” allowing the use of force inside one's own home. The homeowner in Gillis’ case was eventually convicted of second-degree murder and sentenced to 25 years to life in prison. Yarl’s shooter pleaded guilty to an assault charge, but died before he could be sentenced.

Reilly, a Republican, has been Chester’s highway superintendent since 2021. He was re-elected to full four-year term in 2023. He is also a federally licensed firearms dealer.

Asked to elaborate on the criminal possession charges, given that Reilly is a licensed dealer, Kolek says it’s possible the charges against Reilly may change.

“At the time that we were investigating, the facts as they were known, those were the charges that were filed," he says. "Whether or not those are the charges that he ends up being prosecuted for, that’s under the purview of the Orange County District Attorney’s Office.”

The DA did not return a request for comment Monday.

In his own statement, Democratic Town Supervisor Brandon Holdridge says he is “deeply troubled” by reports of the shooting, but the town is not taking a position on the case. The Chester Police Department has recused itself from the investigation, which is being conducted by the State Police in coordination with the DA and the federal Bureau of Alcohol, Tobacco, Firearms and Explosives. Because Reilly is an elected official, Holdridge says the Town Board cannot remove him from office. Holdridge says Highway Department Foreman Keith Meyer will lead the department while the case plays out.

DoorDash says it is cooperating with the investigation. A spokesman wished the driver a “full and speedy recovery” in a statement to WAMC, adding: “No one should ever fear for their safety just for trying to make deliveries in their neighborhood. We’re devastated by this senseless act of violence.”

A preliminary hearing is set for 9 a.m. Friday in Chester Town Court.

Jesse King is the host of WAMC's national program on women's issues, "51%," and the station's bureau chief in the Hudson Valley. She has also produced episodes of the WAMC podcast "A New York Minute In History."