- Ben: Look, I really don't want to crush your childhood dreams, but I bet in your dreams you weren't losing an election by seventy points. You need to get tougher, Leslie. You just have to.
Bobby Newport, heir to the Sweetums corporation, announces his candidacy for the City Council seat Leslie is running for. After two days, he's leading in the polls far ahead of Leslie, despite his lack of intelligence, experience, or interest in politics. Ben and Leslie attend the announcement and introduce themselves to Bobby, who doesn't even know they're competing against him.
Andy isn't feeling well, so he and April consult Ann. They can't afford to go to the doctor, but Ann informs them that they have insurance that will pay for the doctor visits.
Since Bobby refuses to have a debate with Leslie, Ben announces their next campaign strategy: air a campaign ad attacking Bobby Newport during the Pawnee-Eagleton high school basketball game halftime.
Chris approaches Ron to invite him to a meeting at the public works department. Ron agrees to attend when he learns that the meeting is about announcing budget cuts.
Andy and April visit Dr. Harris. Andy has a long list of ailments, some of which Dr. Harris can fix, and he gives them referrals to specialists for the other ailments. They visit several doctors over the course of a week, all the while acquiring new injuries Andy needs to be treated.
Leslie informs Ben that she doesn't like the idea of airing a negative ad as she always dreamed of running a clean campaign. Ben argues that they are just stating the facts about Bobby and pointing out Bobby's obvious flaws is the only way to help her poll numbers, but Leslie wants the ad to state facts about her. Ben suggests they split up into teams, each one making an ad, then they will decide which is better. Leslie chooses Ann and Donna to help her with her positive ad; Jerry is assigned to help Ben. Tom's strategy is to not pick a side so he helps both teams.
Chris thanks Ron for his help and invites him to lunch, much to Ron's discomfort. The following week, he invites Ron to a Japanese tea ceremony. When Ron complains to Donna, she theorizes that he misses Ben, who was his closest friend at city hall and was always the one to deliver bad news.
The time comes to present the campaign ads. Leslie plays her positive ad, which has her state the propositions she supports, though Ben points out that it never states she's running for City Council. Ben's attack ad comes next, attacking Bobby's lack of qualifications and how he wants the election to be handed to him like everything else he's gotten in his life. Everyone votes on Ben's attack ad, much to Leslie's angry dismay. Ben is about to deliver the ad to the TV station but Leslie tackles him and and takes the DVD away. They ultimately miss the window to air the spot and can't get their money back.
Later, Leslie apologizes but says she cannot forsake her morals and she'd rather run the pretend campaign ads she made when she was a kid than use a negative ad. Ben, however, points out to her that she has to get tougher, as the gap between her and her opponent is simply too big for her to be soft on.
April and Andy are given the bill for their hospital visit. They think the insurance will cover it, but there is a $500 deductible of all the doctors that they visited. Since they don't have that kind of money, they take off, only for Andy to run face first into an ambulance parked outside.
Leslie and Ben come to a compromise and make a new ad which includes footage from a fake campaign ad Leslie made as a child. The ad highlights that Leslie was better versed in politics as a child while Bobby has no idea what he's doing. Leslie loves the ad, and it's posted on Youtube, where it's well-received.
In an effort to resolve his problem with Chris' overtures of friendship, Ron introduces Kyle to Chris, suggesting he take Kyle to the tea ceremony. Chris reveals he was not looking for a friend: he was scouting Ron to see if he would be a good replacement for Ben's old job as Assistant City Manager. Ron says he'll consider it.
Leslie and Ben meet with Bobby. He wants them to stop airing their ad, stating that it is mean, and asks Leslie to quit her campaign. When she refuses, he suggests he win the election but let Leslie do all the work. Leslie shoots that down as well and warns him that they will have a debate soon. Bobby is left confused by this and childishly demands Leslie just give him the election. Leslie and Ben leave.
Meanwhile, April and Andy decide going to the doctor is a rip-off and decide never to go to one again.
- Amusing Injuries: Happens to Andy frequently in this episode, including hitting his head against the wall, falling off a chair, and running into an ambulance.
- Attack of the Political Ad: Ben and Leslie toy with airing an attack ad in Leslie's election for city council. Leslie desperately wants to stay positive, even though Ben's attack ad is effective and accurate regarding her Upper-Class Twit opponent.
- Bearer of Bad News: Chris asks Ron to be this, which Ron is happy to do.
- Comically Missing the Point:
- When Andy explains what he knows about insurance, Ann is shocked:Ann: Oh my God, we used to live together.Andy: Aw, you still got it for me.
- Andy gets checked for allergies:Andy: I think based on the redness, I might be allergic to getting stabbed by needles.
- Bobby wonders about the little girl in Leslie's campaign ad, and is surprised when she says it's herself when she was a child.Bobby: How did you do that?
- When Andy explains what he knows about insurance, Ann is shocked:
- Good Is Dumb: Bobby may be quite spoiled and childish, but he really doesn't possess a single mean bone in his body due to being too dim to be otherwise.
- Leaning on the Fourth Wall: The episode has a scene where Chris asks Ron to lunch and Ron declines, and then Gilligan Cut immediately to them at lunch. Ron's next interview segment has him very confused about the time jump, and wondering if Chris drugged him.
- Long List: Leslie's positive ad has a very long one of the things she supports.
- Manchild: Bobby is like a spoiled child in an adult's body, and really doesn't understand how the world works.
- Overly Long Gag: Ben, Jerry and Tom get into a little contest of sorts trying to sound as diabolical as possible when uttering Bobby Newport's name.
- Retcon: Nick Newport Jr. is nowhere to be seen.
- Take a Third Option: Leslie and Ben ultimately come to a compromise for her campaign ad, highlighting both her positive qualities and her opponent's negative ones.
- Upper-Class Twit: Bobby Newport. When Leslie runs a mildly-negative ad against him, he asks her to stop so he can just easily win. She of course says no. This doesn't make him angry though - it just makes him confused. He also has no idea how videos work.
- Wise Beyond Their Years: Even as a little kid, Leslie was well versed in politics.