Motions in Alpha Barry’s suit against Town of Chester and its former highway superintendent slated for consideration May 1

Motions in Alpha Barry’s civil suit against former Chester Highway Superintendent John Reilly and the Town of Chester are scheduled to be considered May 1 in county supreme court.

Barry is the lost DoorDash driver shot by former Chester Highway Superintendent John Reilly.

The lawsuit filed in November 2025 says it is “a civil action for compensatory damages for the negligence, recklessness and carelessness of defendants, their agents, servants and/or employees. This case arises from the assault and battery, negligence, intentional infliction of physical and emotional distress resulting from the negligence of John Reilly and the Town of Chester at the time of the incident, as a result of their negligence, negligent supervision...Defendants’ conduct was negligent and/or reckless and caused the Plaintiff to be physically injured, it has caused and continues to cause substantial economic and non-economic damages, physical and emotional distress.”

In his response to the complaint, Reilly denied liability and asserted defenses claiming that Barry was legally responsible for his injuries. He also filed claims against the Town of Chester alleging that it should indemnify him in part or in full for any damages Barry recovered. The Town of Chester moved to dismiss the claims against it on the grounds that Reilly was acting outside the scope of his employment and that it was not negligent with respect to hiring, training, retaining or supervising him.

Barry is represented by attorney Rudyard Whyte of The Cochran Firm, based in Manhattan.

Whyte said, “We are at the discovery stage so we have to investigate everything we can on behalf of Mr. Barry, and that includes finding out what the town knew and when they knew it and things like why the town highway superintendent was running around with nine unlicensed guns. We are in the early part of the litigation – in discovery.”

Whyte said Barry lost 26 inches of intestines and has undergone several surgeries as a result of the shooting.

Town of Chester Supervisor Brandon Holdridge said the town has no comment on the matter.

Attempts to contact Reilly’s attorney, listed in court filings as Jeffrey Sherwin of Middletown-based MacVean Lewis Sherwin & McDermott, were unsuccessful by deadline.

Judge E. Loren Williams is listed as the presiding judge in the legal action.

Reilly was removed from office once found guilty of assault causing injury through risk of death and other offenses in county court for the May 2025 shooting of Barry on Reilly’s Valerie Drive property.

“Per New York State law, Mr. Reilly is vacated from his office as soon as he is convicted,” Holdridge said hours after Reilly was found guilty. “We directed the town clerk to put out a notice for intertest in the highway superintendent position. We will give people two or three weeks to get back to us and then we will interview every person who submitted a letter and choose from that pool the person we think is the best fit for the interim position. Whoever we appoint will serve until the end of the term, which is the end of 2027.”