The gang is hanging at the bar as usual when Frank comes in bitching about how corrupt the city council is. Sweet Dee remarks something about what she would do if she were a councilwoman. Dennis' belittling response to this causes Dee to argue the point, and eventually decide to run in the upcoming election.
"The Gang Starts a SuperPAC"
Charlie volunteers to be campaign manager, and the two go down to city hall to register her as a candidate. The conversation with the city hall employee is absurd but they are eventually told that they will need a petition with a bunch of signatures to be on the ballot.
Soliciting for signatures doesn't go well. Dee is not able to articulate her qualifications or intentions as a candidate, and dry heaves in front of crowds. Back at the bar, Dennis ridicules Dee for thinking she could run and Charlie for managing worse than he thought was possible. Charlie argues that, while Dee is stupid, it doesn't really matter. All that matters is money, which is why they're going to start a SuperPAC and get a bunch of rich people to fund the campaign.
The next day, Charlie gets a notification that the SuperPAC received a large donation. Upon seeing this, Dennis decides that if a dumb bird like Dee can get wealthy donors, a reasonable candidate like himself would get a fortune and could probably outspend the other candidates. He takes Mac as campaign manager/bodyguard.
After registering, Dennis receives a notification that his SuperPAC has also received a donation. They want to spend it on attack ads, but they don't know the other candidates. So they spend it all on attack ads against Dee. The more ads they run, the more donations come in. The ensuing ad war humiliates both sides, and Cricket is eventually employed in a bungled assassination attempt.
Ultimately, they're both overwhelmingly defeated in the election. News coverage of the election results show Frank at the victor's election party celebrating. Later, Frank reveals that he had been funding both sides through one of his shadow organizations, initially because he always hedges his bets in city elections (that's why he can park wherever he wants), but eventually because the ad war was worth every penny.