Highway superintendent charged with attempted murder in DoorDash shooting

CHESTER. Town officials urge Highway Superintendent John Reilly to resign.

| 20 May 2025 | 10:40

Chester Highway Superintendent John Reilly has been indicted on attempted murder and other felony charges in connection with the alleged May 2 shooting of DoorDash delivery driver Alpha Oumar Barry, prosecutors announced Monday.

In addition to second degree attempted murder, which is a Class B felony, the charges covered in the indictment, according to the Orange County District Attorney’s Office, are two counts of first-degree assault (Class B violent felonies), second-degree criminal possession of a weapon (Class C violent felony), second-degree assault (Class D violent felony) and eight counts of criminal possession of a firearm (Class E felonies).

Reilly’s arraignment upon the indictment, seen here, has yet to be scheduled by the county court, said Ryan Greenbaum, a spokesman with the Orange County District Attorney’s Office.

It remains unclear how much prison time Reilly may face if convicted.

“It’s difficult to say what the maximum exposure is because it requires certain legal and factual findings – including whether any convictions can run consecutively versus concurrently,” said Ryan Greenbaum with the DA’s office.

Reilly is accused of shooting Barry, who reportedly was attempting to deliver food to a home in the Valerie Drive neighborhood when he became lost and unable to navigate using the app.

Police say the victim had approached several homes asking for directions before arriving at Reilly’s residence.

Reilly told the victim to get off his property before allegedly firing multiple shots at him as he attempted to leave, striking Barry once in the back.

According to a state police press release, the Middletown Bureau of Criminal Investigation was notified of a gunshot victim at Garnet Health Medical Center about 9:50 p.m. Friday, May 2. Reilly was arrested May 3.

‘Far more complex’

Reilly is represented by New York City-based Raiser & Kenniff, which also represented Daniel Penny, who was found not guilty last year of criminally negligent homicide in the death of Jordan Neely during an incident on the New York City subway.

Khiabeth Burgos, a legal assistant with the firm, emailed the following statement to Straus News, on behalf of Reilly’s attorney Thomas Kenniff:

“The right to defend oneself and one’s family from harm is as old as the law itself. Nowhere is this right more closely guarded than within the sanctity of one’s home. The situation confronting my client on the evening in question was far more complex than has been portrayed. The purported DoorDash driver, who wore no uniform and bore no credentials, was seen moments earlier unlawfully entering the garage of a next-door neighbor. He then approached Mr. Reilly’s door without invitation, bizarrely asking to enter his home, while Mr. Reilly’s wife and young daughter were inside. Mr. Reilly’s intention was not to cause harm, but to warn this man off his property after he had resisted his requests to leave. We are confident that once all these facts are brought to light, Mr. Reilly will be absolved of any wrongdoing.”

Call for resignation

“I asked him to submit his resignation over the phone [Wednesday, May 14] and he said he had no intention of resigning,” Chester Town Supervisor Brandon Holdridge told Straus News. “At that point, I let him know that on behalf of the board and myself, we would be releasing a public letter calling on him to resign to which he said he understands. We then released the public letter on social media and I read from it at the town board meeting that night.”

The letter, which is signed by Holdridge and each town councilman, says, in part:

“Many have demanded that Mr. Reilly be fired. As an elected official, the town board does not have the legal authority to remove Mr. Reilly as highway superintendent. Pursuant to Public Officers Law, the position only becomes vacant upon resignation or conviction of a felony crime. The board strongly believes that every individual is entitled to due process and that Mr. Reilly is presumed innocent until proven guilty. However, these past 10 days have demonstrated the seriousness of this shooting.”

Reilly is working remotely, according to Holdridge and highway department personnel contacted by Straus News.

Threats to town employees

The letter signed by Holdridge and town councilmen calling for Reilly’s resignation also refers to the case having become a safety issue for the town, its employees and its residents.

Holdridge said Chester police are investigating threats as they come in, though he is not aware of any leads.

“Many of our employees have been getting calls and emails from people using expletives with threats to residents and staff, including myself,” he said. “They say things like, ‘How would you like it if I were to come up there and shoot you guys in the back?’ or ‘You guys are a bunch of racists and should all be getting the same treatment the driver did.’ When these messages are received, they are passed along to our police. They seem to be from out of town and further stress how this is serving as a distraction and that is one of the reasons we are calling for (Reilly) to resign.”