The Parks Department helps build a playground in Eagleton with the Kaboom company. Leslie and Ann run into Andy, who claims to be volunteering, but in reality, is coming for the free food, and he tells them that he isn't living in the pit anymore. Leslie, inspired by the Kaboom project, consults with her team. Mark tells her to just fill in the pit: "Don't ask for permission, ask for forgiveness."
Leslie and Ann rent a bulldozer, and the operator begins filling in the pit. Unfortunately, Andy was in the pit gathering his things and gets a concussion when mounds of dirt and rocks land on him, and he has to go to the hospital. As Ann tends to him, Andy tries yet again to win her back. Ann pointedly tells Andy that she's happy with Mark. Andy asks Ann what Mark has that he doesn't have, and she replies with "a job, a car, a steady income, an address." Ann gets another nurse assigned to him. Disheartened, Andy decides he needs to get money to win her back.
Ron, having been scolded by the City Manager, scolds Leslie, as the town is now open to a large potential lawsuit from Andy, and he sends her to visit him along with their city attorney. Leslie tries to visit Andy in the hospital but is stopped by city attorney Scott Braddock, who informs her that Andy could sue the city and Leslie needs to be careful not to take the blame for his injuries. While she and Scott are visiting Andy, Andy's lawyer Wendell Adams shows up – Andy is suing the city as his "only option". Leslie wants to talk about the situation, but neither lawyer will let his client speak.
Leslie tries to get in touch with Andy so they can talk without their lawyers present. She has no luck, but Ann offers to help. She calls Andy and gets him to meet her at her house. Unfortunately, Andy thinks Ann is calling to get back together with him, so he appears at her door naked. Ann takes off and leaves Andy and Leslie to have their talk.
Andy thinks he needs a lot of money to get Ann back. Leslie tells him that she recently learned that it's not a good idea to take shortcuts. Andy decides to get a job. Leslie suddenly gets an idea.
As part of Leslie and Andy's plan, Leslie and Scott meet with Andy, who says he'll drop the lawsuit on the condition that the pit gets filled in. The lawyer agrees, and the pit is finally filled. Leslie tells Ann that Andy gave up the lawsuit.
Leslie tries to call Kaboom so they can put a playground on the new lot, but there is no such thing as Kaboom. It was just a prank by the "leader".
Tropes:
- Batman Gambit: Leslie and Andy pull one to get the pit at Plot 48 filled in. Andy gets injured in the pit for a second time when Leslie tries to fill the pit without authorization, putting Pawnee at risk of a lawsuit if Andy were to sue. Leslie persuades Andy to sue the city and say he'll drop the lawsuit if the pit gets filled in, which winds up working.
- Dramatically Missing the Point: Andy thinks Ann's only concern is that he has little next to no money to his name, when really it's his lack of a real job and future.
- Embarrassing Voicemail: Leslie tries to find out why Andy is suing by calling him. He doesn't answer, so she leaves a very awkward voicemail.Leslie: Hey, Andy, it's your aunt. Your mom or dad's sister. I don't know how to tell you this, but... your uncle has passed. He's with Jesus now. So we're having a memorial in 30 minutes at city hall. Because of a local disaster, you... Andy Dwyer... must go to the evacuation center at Pawnee city hall...
- Foreshadowing: Due to Jerry using a permanent marker when Leslie tries to erase all the procedures they would need to use to get the pit filled in, she is unable to do so. This hints at the fact that they cannot bypass all the red tape, and even with the pit filled in, there is still a long way to get the park built.
- Frivolous Lawsuit: Subverted; Andy does have a case against the Pawnee government (and he can win a lot of money for it), and Leslie has to convince him not to do it.
- What's He Got That I Ain't Got?!: Andy asks Ann this with regards to Mark. Ann is somewhat aghast that he doesn't realize how obvious the answer is, as Mark is actually a mature adult with a job while Andy himself is unemployed and only just recently moved in with his friend.
- What the Hell, Hero?: Ron chews out Leslie for going behind his and the city's back to fill in the pit, because it ends up causing a potential lawsuit for the city when Andy turned out to still be living in the pit.
