Chestertown Ward 1 Council member Tim O’Brien submitted a letter of resignation to the Chestertown Town Council this week. The Chestertown Spy reports the letter follows a legal filing and ongoing litigation claiming O’Brien’s residential move from Ward 1 to Ward 4 immediately disqualified him from holding the Ward 1 seat as per the town charter and that the amended Resolution (No. 06-2023) only allows future candidates the allowance to move to a different ward after two years of service, not retroactively.