Gary travels to Wisconsin in the aim of getting this man, Jack Hastings, to campaign in the upcoming mayoral election, and while his initial plan is to simply provide resources to the effort, that changes when Jack says that he will only run if Gary serves as his campaign manager. He reluctantly agrees, as he is forced to make a major personal adjustment to small-town life, but a fire is lit underneath him when his rival, Faith Brewster (Rose Byrne), having gotten wind of Gary’s activities, arrives on the scene to support the opposition, incumbent Mayor Braun (Brent Sexton). Washington tactics slowly ensconce the little burg as more and more money is poured into the race, the two strategists employing their entire playbooks in attempts to one-up the other.