Chester Town Official Found Guilty in Driveway Shooting

GOSHEN, NY — A Chester town official was found guilty by an Orange County jury on Thursday for shooting a delivery driver last year.

Town Highway Superintendent John Reilly was found guilty of multiple charges, including assault in the first degree for depraved indifference, criminal possession of weapon in the second degree, assault in the second degree, and eight charges of criminal possession of a firearm.

The May 2, 2025 shooting occurred when DoorDash driver Alpha Barry appeared at Reilly’s home.

Barry, who had immigrated to the U.S. from Guinea about a year prior and spoke limited English, claimed he was asking for directions after his phone died.

Reilly’s defense claimed Barry had asked to come inside several times and did not answer Reilly’s questions.

Video footage shown to the jury shows Reilly later firing at Barry’s vehicle as he tried to leave. Barry was struck in the back as he left Reilly’s driveway.

Reilly never called 911, but had contacted someone he knew in law enforcement. The following day, police searched Reilly’s home and found several guns, for which Reilly did not have permits or licenses.

After Reilly was handcuffed and remanded to the Orange County jail without bail, his attorney Thomas Kenniff said he plans to appeal.

Kenniff said the ruling was “bittersweet.”

“We feel vindicated in the sense that the jury found, as we said all along, that Mr. Riley did not act with any intent to harm or any intent to kill, and the jury agreed with that,” he said. “We’re obviously tremendously disappointed with the depraved indifference conviction, particularly because we feel most strongly that that should have never been included in the indictment.”

Orange County District Attorney David Hoovler told WAMC he doesn’t see this case as an example of racialized violence, but an example of when you should and should not use a gun.

“This case is a stark reminder to everybody that owns a gun that there’s a responsibility that comes with that. And when you pull that gun, and when you fire that gun, there is no taking that bullet back ever,” he said. “It’s a forever event when you fire that gun, when he fired that gun, he caused everlasting injuries to the victim, in this case, who will never be the same. His bodily function will never be the same, and Mr. Reilly and his family will never be the same.”

Hoovler explained the video of the shooting was essential to the case and gave the jury a bird’s eye view of the event.

He also explained the attempted murder charge was not considered after Reilly was found not guilty of assault (intentional) in the 1st degree. The top charge of assault in the 1st degree (depraved indifference) carries a maximum sentence of 25 years in prison.

The DA explained how he thought the sentencing would go.

“It is more than likely how this case will be sentenced. He’ll be given a determinant number of, like, 15 years or 12 years or 20 years, and then everything else will be rolled into that,” Hoovler said.

Reilly was removed from his position as highway superintendent after the jury’s verdict.

Chester Town Supervisor Brandon Holdridge said the shooting should not have happened.

“I think it was awful,” he said. “And, yeah, no, it was, it was awful. It shouldn’t have happened, and that’s why the town board unanimously called for Mr. Riley’s resignation, like a day or two after the events originally.”

Holdridge said Chester, which has been mired in controversy for nearly a year, just wants to move on.

“It’s been a very interesting time for Chester, but you know, hopefully [Barry] Alpha is doing well, and, yeah, hopefully we can get somebody in the highway garage to be able to lead the department.”

Reilly will be sentenced on May 18.

By New York Public News Network | Elias Guerra, WAMC News

Image: John Reilly, Town of Chester highway superintendent, is handcuffed after the jury delivered a guilty verdict. (Elias Guerra)