Former Chester highway superintendent sentenced to 17 years in shooting case

John Reilly III was sentenced to 17 years in state prison and five years of post-release supervision, but the case remains active because his defense says it will appeal the conviction that ended his tenure as Chester highway superintendent.

Orange County prosecutors had sought 21 1/3 to 24 years behind bars for the 49-year-old former town official, who was convicted by an Orange County jury on March 26. The district attorney’s office said the jury found him guilty of first-degree assault, second-degree weapon possession, second-degree assault and eight counts of criminal possession of a firearm. Some local reporting described nine firearm-possession counts, a discrepancy that will be settled by the court record. The judge ordered the remaining sentences to run at the same time as the 17-year term.

The conviction grew out of the May 2, 2025, shooting of DoorDash driver Alpha Oumar Barry at Reilly’s home in the Town of Chester. Prosecutors said Barry was unarmed, lost and unable to charge his phone when he walked to the property with a bag of food and asked whether Reilly had ordered it. According to the district attorney’s office, Reilly told Barry to leave, came out with a shoulder holster and a .45 caliber Glock pistol, racked the weapon, fired into the lawn, then fired at Barry’s vehicle as Barry tried to drive away. One bullet struck Barry in the lower back.

The injuries were severe. Emergency surgery removed more than two feet of Barry’s small bowel, and his attorney, Rudyard Whyte, said Barry lost 26 inches of intestines and will never fully recover. Whyte said Barry was relieved by the verdict.

Investigators said a search of Reilly’s home recovered the Glock, the shoulder holster, .45 caliber casings, a projectile from the front lawn and seven other illegally possessed pistols. Prosecutors said Reilly had a federal firearms license to sell guns, but did not have a New York State firearms license or pistol permit, which meant he could not lawfully possess those weapons in New York. Orange County District Attorney David M. Hoovler said the case was not about race but about the responsibility that comes with using a gun, and that once a bullet is fired, it cannot be taken back.

Defense attorney Thomas Kenniff said after sentencing that the case is headed to appellate court and that the appeal will challenge, among other things, the decision to send the depraved-indifference count to the jury. The conviction also triggered a political fallout in Chester: Town Supervisor Brandon Holdridge said Reilly was vacated from office under New York law as soon as he was convicted, and the town moved to find an interim highway superintendent to serve through the end of 2027. Barry also filed a civil suit against Reilly and the Town of Chester in November 2025, keeping the public accounting far from finished.