From 1988 to 2002, Shays was reelected fairly handily, never dropping below 57 percent of the vote even as the 4th turned more Democratic at the national level. The district, once a classic "Yankee Republican" district, swung heavily Democratic along with the rest of Connecticut from the early 1990s onward; the last Republican presidential candidate to carry it was George H. W. Bush in 1988. However, in 2004, Westport First Selectwoman Diane Farrell held him to only 52 percent of the vote, his closest contest in two decades.
