Jake surprises Amy with an investigation into a string of arsons connected to her favorite crossword puzzle author, Vin Stermley (guest star David Fumero). Meanwhile, Gina helps Holt jazz up his commissioner candidate speech, and Terry, Rosa, Hitchcock and Scully argue over who is most deserving of the new detective car.
The show begins with Captain Holt announcing that Amy's Sergeant exam result has arrived. It is revealed that Amy has passed and is becoming a Sergeant. The detectives are awarded with a typical Santiago victory dance.
Jake wants to make the last case he works with Amy as a detective as the best case ever. So, he chooses an arson case that is connected to the Saturday puzzles. Guest actor David Fumero (Melissa's husband) guest stars as Melvin "Vin" Stermley, the smoldering hot puzzle-master / model. As the case progresses, Jake starts to feel the beginnings of jealousy. They solve the case at the end and Jake voices his feelings to Amy.
On the other side, Gina and Holt attend the meet-and-greet for the Commissioner election where they come to know that one of the three identical while males running has withdrawn to be replaced by a young female Captain Olivia Crawford. Crawford wants to eliminate precincts and constantly mocks Holt for his age, declaring each other their nemeses. In his quest to win the post, Holt tries to talk to the Chief and comes to realize that Olivia is not being considered as a "serious" candidate and is only in the running for PR reasons. He gives an opening speech where he threatens to withdraw if everyone in the running isn't treated equally. Crawford thanks Holt for standing up for her and they declare each other "frenemies".
|Andy Samberg||...||Jake Peralta|
|Stephanie Beatriz||...||Rosa Diaz|
|Terry Crews||...||Terry Jeffords|
|Melissa Fumero||...||Amy Santiago|
|Joe Lo Truglio||...||Charles Boyle|
|Andre Braugher||...||Captain Ray Holt|
|Chelsea Peretti||...||Gina Linetti|
|Dirk Blocker||...||Michael Hitchcock|
|Joel McKinnon Miller||...||Norm Scully|
|David Fumero||...||Melvin "Vin" Stermley|
|Will Shortz||...||Sam Jepsen|
|Allison Tolman||...||Capt. Olivia Crawford|
|Alan Brooks||...||John Kelly I|
|Stewart Skelton||...||Patrick Faricy|
- Charles says Jake sounds like Caesar Flickerman from The Hunger Games film series.
- Parade magazine is mention, in regards to an American nationwide Sunday newspaper magazine that's distributed in more than 700 newspapers in the United States.
- Will Shortz made a cameo (as Sam Jepsen) in this episode.
- Melvin mentions he and Anna Kournikova were together in the past but broke up. Kournikova is a professional tennis player who gained attention more for her appearance than her sports career.
- Terry confesses that he rigged the car draw by freezing his slip of paper so that he'd select it. A popular conspiracy regarding the 1985 NBA draft lottery, which determined who would likely draft Patrick Ewing, was that the envelope for the New York Knicks - Jake's favourite team - was placed in a freezer and bent so that it would be easier for commissioner David Stern to select it.
- Melvin "Vin" Stermley is played by David Fumero, the real-life husband of Melissa Fumero.
- Amy makes her last appearance as a Detective in this episode.
- Captain Holt tells Captain Crawford that he is too dignified to use a portmanteau. However, he has previously said “bingpot”, Jake’s portmanteau of bingo and jackpot.
- The solution to the anagram "Sad Anus Loser. I go in." is 1988's "Dangerous Liaisons".