Fairfield County, like many affluent suburbs, has been drifting left in recent years. The 4th Congressional District hasn’t been represented by a Republican since early 2009, after incumbent Chris Shays lost his seat to the current occupant, Rep. Jim Himes. In 2016, Hillary Clinton won every community in lower Fairfield County, including Greenwich and New Canaan, towns which Republican Mitt Romney had swept four years earlier. The following year, Democrats successfully flipped town leadership positions in several Fairfield County towns, including in Weston. The midterm elections in 2018 saw a further intensification of this blue wave.