A Democratic strategist helps a retired veteran run for mayor in a small, conservative Midwest town.
Democratic political strategist Gary Zimmer hits a snag in his career following Donald Trump’s election in the 2016 presidential race. When he comes across former marine Jack Hastings from the small town of Deerlaken, Wisconsin, he sees it as an opportunity to get the country to vote blue next if he gets Jack to run as a Democratic nominee for mayor. They go up against incumbent Mayor Braun and Gary’s rival, Faith Brewster.
After many dirty tactics, Gary learns that he took the bait set up by Jack and his daughter Diana to get the campaign to bring in donations to Deerlaken since it has been struggling lately. After a special election, Diana is named mayor, and Gary enters a sexual relationship with Faith.
Successful Democratic campaigner Gary Zimmer is in despair due to the results of the 2016 election. Gary is shown a viral video of Marine Colonel Jack Hastings giving a speech standing up for the undocumented immigrant population living in his hometown of Deerlaken, Wisconsin. Deciding that if he can run Hastings as the Democratic mayoral candidate in the next election, he can convince the American people in the heartland to vote democrat in the next presidential election. Arriving in Deerlaken, Gary immediately finds his city slicker Washington DC attitude contrasting to the townspeople more rural mannerisms.
Gary soon meets Hastings and his daughter Diana and pitches his idea. Hastings initially declines considering himself more of a conservative and having no real interest in politics, but later relents and agrees to run under the condition that Gary runs his campaign. Hastings recruits his friends and neighbors as volunteers for the campaign. However, setbacks soon arise including the fact that most of the town is conservative and the fact that the incumbent Mayor Braun is being funded by the Republican National Committee. The RNC also sends down Faith Brewster, Gary’s nemesis, to counter Gary.
The election soon heats up and Gary takes Hastings to New York so they can recruit fundraisers for the campaign to match Faith’s money and reinforcements. Hastings gives a powerful speech to the possible donors about how he needs their help for his small town which inspires Gary. Their donations allow Gary to upgrade their campaigning methods. Soon the election polls show Hastings and Braun neck in neck although the Hastings’ campaign takes a dive when one of Gary’s team members promises the schools free contraceptives paid for by the government which irritates a group of nuns. When Gary starts berating his teammates, Diana convinces him to apologize and that if he is going to run her father’s campaign, he needs to be nice.
When it starts to look like Faith and Braun are going to win, Gary tries to convince Hastings and Diana to play dirty and start exploiting Braun’s skeletons. Diana is horrified that Gary would play dirty and goes to Braun for advice. Braun and Diana decide to secretly reveal a bigger scandal about Braun so Gary won’t go after Braun’s brother which was his original plan. The scandal, however, proves to be false.
On Election Day, no one votes which confuses both Gary and Faith. It is revealed that the election was actually a setup. Diana shot the video of her father’s immigration speech so that Gary and Faith would pour thousands of dollars into the election which would help the town through its financial trouble due to the recent closure of the military base. Gary is shocked that Diana would play him and Diana then counters him by explaining the town set this up because DC politicians play small towns like theirs all the time. When Gary reveals that he was hoping that there was a spark between them, Diana rejects him. Later, Gary and Faith enter into a sexual relationship and Diana becomes the mayor of Deerlaken after a special election.
The film starts in 2016 just before the presidential elections. The voices of Hillary Clinton and Donald Trump can be heard over their debate. Strategists from both parties – Democrat Gary Zimmer (Steve Carell) and Republican Faith Brewster (Rose Byrne) – tell the press exactly what they want to hear and await as their candidates prepare for Election Day. After Trump’s election, Gary’s career falls into a decline.
In Deerlaken, Wisconsin, former Colonel Jack Hastings (Chris Cooper) goes to a town hall meeting where he protests the shutdown of a program that would benefit undocumented immigrants. A video of him sticking up for them goes viral and gets Gary’s attention. He resolves with his team that he can get Jack to run as the Democratic nominee for the town’s mayor in an effort to bounce back and get the country to vote blue in the next presidential election.
Gary flies to Deerlaken and is greeted by the quirky locals. He rents out a place above the local pub. The day after he arrives, he goes to Jack’s house to meet him and his daughter Diana (Mackenzie Davis). Gary does his best to convince Jack to run for mayor, even though he is not interested at first since he leans more conservative. Gary manages to get Jack on board as long as he promises to run the campaign himself.
Gary and Jack begin the campaign run by having Jack announce before a small press gathering that he is running for mayor, but it’s done so awkwardly because he doesn’t know what to do, and Gary had cows set in the background for a more authentic rural look. Gary spends more time with Jack and they get some of the townspeople involved in the campaign, like the bartender or cafe owner he keeps seeing.
Soon, Faith is sent by the Republican National Committee to help Jack’s opponent, incumbent Mayor Braun (Brent Sexton), win re-election. Gary knows she is around when he sees a billboard for Braun with an unnecessary semicolon because Faith is notorious for that type of thing. Diana and the other townsfolk see this as a blow to their campaign, but Gary is unfettered because he views the Republicans move as an act of desperation. Gary also spends more time with Diana, trying to form a connection with her and hearing her overall desire to fight for the town.
Gary and Faith’s rivalry drives his desire to push the campaign further to his advantage. They each use their own tactics to piss each other off, which starts to bring Jack’s numbers higher and Braun’s numbers lower. Gary then decides to bring Jack to New York to score donors for the campaign. When they are brought before a bunch of potential donors, he gives a rousing and honest speech regarding the need for donations and why he should be trying to convince them to do so. The speech ends up moving them and earns them a victory. Gary uses the donations to upgrade the campaigning methods, like giving them WiFi access instead of the dial-up they had to use. He brings on his own people like Kurt (Topher Grace) and Tina (Natasha Lyonne) to help. However, Gary acts like a jerk to the volunteers, and Diana has to tell him to behave better if he wants them to work with him.
The campaign hits a snag when a group of nuns threatens to boycott them when they learn that one of Gary’s team members promised that the government would pay for contraception for schools. Conservative news outlets like Fox News also try to hurt Jack’s name by pitting him against the veteran demographic by showing that he has aligned himself with Democrats. When Gary tries to talk to Jack and Diana about the campaign’s potential failure, they seem fine with it, but Gary wants to keep it going and stoop to the Republican level to try and dig up dirt on them. Diana is put off by Gary’s attempted tactics, and she even goes to Braun himself for advice.
A new scandal appears to arise in the form of Braun supposedly having conceived a lovechild out of wedlock, but the scandal proves to be false. Braun and Diana try to put out a bigger scandal to discredit the other “scandal”, but everything is dropped after it turns out to all be a hoax.
The day of the election arrives, and Gary learns that one of his team members orchestrated things to bring him to Deerlaken. Gary and Faith see that nobody voted, so they rush to city hall to find that Jack and Braun are apparently tied. When Gary tries to get to the bottom of things, he learns that he has been played from the jump. The whole viral video of Jack sticking up for immigrants was set up, as was the whole election. It was planned by Jack and Diana as a means to get donations to the town since it had been struggling for a while, and they knew all the incoming donations would benefit them. Gary realizes he got fooled, and he tries to make one last shot with Diana, but she says he is too old for her, and she also points out how other politicians exploit small towns like Deerlaken for profit, so they tried a similar tactic. Faith, however, is impressed by the whole gambit.
Six months later, Jack and Diana are shown making plans for something new in town. Gary then comes out and appears to be in a relationship with Diana. This proves to be a fantasy of his, and he’s with the cafe woman. This is ANOTHER fantasy, and he’s actually now in a sexual relationship with Faith. Additional text states that after a special election, Diana was elected mayor of Deerlaken.