On September 23, 2026, Mayor Chuck Grassie attended the Dover City Council meeting to settle a friendly bet he made with Mayor Dennis Shanahan. The bet was placed on the outcome of a recent football game between longtime rival varsity football teams, Spaulding Red Raiders and Dover Green Wave. Each mayor agreed to wear the hat of the opposing team at their next City Council meeting if they were to lose. Fortunately for Grassie, Spaulding High School won the game, securing an amazing 21-0 win. During the opening of the meeting, Shanahan was presented with a Red Raider hat, which Grassie delivered personally.