The mayor has a tree cut down to impress his new girlfriend. Unfortunately, it was a tree planted by George Washington in 1796. Meanwhile, Charlie has a one-night stand, who turns out to be a rival mayoral candidate's campaign manager. Mike helps out with crisis control. Charlie and Caitlin decide to be friends for the time being, while Mike announces his return to City Hall.

Carter's friend Michelle visits and begins dating Stuart. However, Carter has just asked her to be his child's surrogate mother. Meanwhile, Charlie and Caitlin struggle over what to do with incriminating photos of the mayor's opponent.

The Mayoral race hits a snag when Mayor Winston's opponent suffers a heart attack which forces him to drop out of the running, but his wife, Nancy Wheeler, steps in to take his place and surges in the polls due to an outpouring of sympathy. Meanwhile, Charlie gets punched in the face by Caitlin's new love interest and she makes him promise to be the bigger man by not fighting back.