The Entire Brooklyn Nine-Nine Timeline Explained

Getting into the NBC police comedy Brooklyn Nine-Nine doesn't take a lot of background. Plot-wise, it isn't exactly Westworld. All you really need to know is the sitcom features the exploits of a precinct of police officers who are absolute super cops in some ways and bumbling morons in others.  

But that doesn't mean there isn't a lot to be gained from knowing more about the background of these well-meaning yet flawed detectives. For invested fans of the series, the return of some of the beloved recurring characters — whether they're dangerously traumatized undercover cops or chest-pounding parasites who swoop in occasionally to steal the squad's glory — add a lot of flavor to the show. And when you hear Charles Boyle (Joe Lo Truglio) innocently oversexualize another turn of phrase or watch Terry (Terry Crews) go ballistic over yogurt, it's that much funnier when you know it's something they do just about every episode. 

Whether you're a new fan or you've been there from the beginning and just enjoy hearing about your favorite dysfunctional police squad, here's the timeline of Brooklyn Nine-Nine explained.

Brooklyn Nine-Nine begins on the day the squad gets a new commanding officer in the form of Captain Raymond Holt (Andre Braugher). Holt's no-nonsense, rule-stickler style is a bit of a shock to the squad, who'd gotten used to the extremely hands-off approach of their previous C.O., Captain McGinty (Mike Hagerty). Through flashbacks we learn that the detectives got away with just about anything under McGinty's command, including staging "fire extinguisher races" at work. In contrast, one of Holt's first commands is to demand Jake Peralta (Andy Samberg) start wearing a tie — a directive Peralta undermines in every way he can, whether that means wearing the tie around his waist or wearing a shirt and tie without pants.

In spite of his stricter approach, it doesn't take long for Holt to win the squad's respect. They learn he's a legendary detective in his own right. Among other things, he's known for capturing an infamous '70s serial killer, the yo-yo wielding Disco Strangler. The only reason the Nine-Nine is his first command is because as a Black, openly gay cop, he's faced more than his fair share of ignorance and intolerance. To Peralta, he'll become a father figure, and to Amy Santiago (Melissa Fumero), he'll prove an able mentor. Regardless, the squad can never truly read their new C.O.'s mood. Whether he's saying "I lost everything" or "that is amazingly funny," he delivers it in the same stoic, monotone style.

In the beginning of the series, Jake and Amy are rivals in the middle of a contest to see who will make the most felony arrests. But by the end of the first season, it's clear Jake feels more than friendship towards Amy. He reveals his feelings for her in the season 1 finale, in spite of Amy being in a relationship with Teddy (Kyle Bornheimer). Despite their often clashing personalities, Jake and Amy begin dating in season 3. In season 5's "HalloVeen," Peralta uses the hijinks of the annual Halloween Heist to propose to Amy in the evidence room, and she accepts. Regardless of bomb threats and a host of other mishaps, the pair are married in the season 5 finale. The ceremony takes place in the precinct parking lot, with Captain Holt officiating.

In the season 7 finale, Amy gives birth to her and Jake's first child during a city-wide blackout, and she's forced to have her baby at the precinct. Hitchcock (Dirk Blocker) and Scully's (Joel McKinnon Miller) long hours of relaxation serves them well in making a birthing suite for her, while Terry and Holt swallow their pride and dance to Salt-N-Pepa's "Push It" to distract her from her pain. Jake makes it back to the precinct in time to witness the birth of their son, who they name Mac after John McClane — the hero of Die Hard, Jake's favorite movie. 

The heroes of Brooklyn Nine-Nine deal with a few recurring antagonists, and the first one we meet is Keith Pembroke (Dean Winters), better known as "the Vulture." As a detective working for NYPD's Major Crimes Unit, the Vulture has the authority to take over any case he wants, and he uses that power to help his career at the expense of everyone else. The Vulture regularly waits until felony cases are almost completely resolved, and then he swoops in at the last minute to take all the credit. 

The Vulture becomes part of the squad's lives in a big, bad way in season 3. After Captain Holt is promoted to the head of the NYPD's public relations office, Captain Seth Dozerman (Bill Hader) takes over as C.O., but his time with the squad doesn't last long. He dies of a heart attack in the season 3 premiere. The episode ends with the reveal that the Vulture is taking over as captain. 

The Vulture's time as captain is as rough on the squad as you'd imagine. Among other ridiculous demands, he orders Jake and Amy to stop dating, tells the entire squad to only pursue misdemeanors because of a bet he has with another captain, and fills Holt's old office with kettle bells and protein shakes. Thankfully for everybody, at the end of "The Oolong Slayer," Jake solves a case and lets the credit go to Police Chief Garmin (Tim Powell) in exchange for bringing Holt back to the precinct.

In season 1's "Halloween," Jake bets Captain Holt that by the end of the night, he can steal the Medal of Valor from Holt's office. By the end of the episode, Peralta has Charles deliver Holt's medal to him. As the loser of the challenge, Holt has to do all of Jake's paperwork for the night and to call Jake an "amazing detective/genius" in front of the rest of the squad. However,  "Halloween" proves to be only the first of what comes to be known as the annual Halloween Heists (though not all take place on Halloween), where they try to steal a new object each time. And each heist episode ends with the winner describing the clever methods of misdirection they used to win the contest. 

While Jake and Holt are the only competitors in the first heist, after "Halloween," everyone starts getting in on the action and very little is out of bounds. And starting with season 4's "Halloween IV," Bill (Winston Story) — a Charles Boyle lookalike — becomes a regular fixture in the heists, always revealing more disturbing details about his life than anyone wants to hear. Holt regularly brings his adorable Corgi, Cheddar, into the competition, and he soon learns his squad isn't beyond swapping the pooch with a replacement Corgi to get ahead. Things get so fierce that when Jake uses the object of the pursuit — a championship cummerbund — to propose to Amy in season 5's "HalloVeen," Santiago initially thinks the proposal is a fake-out to beat her in the heist.

Perhaps no two TV characters more aptly embody the word "frenemies" than Brooklyn Nine-Nine's Jake Peralta and his sometimes nemesis Doug Judy, aka the Pontiac Bandit (Craig Robinson). 

Judy first appears in season 1's "Pontiac Bandit," offering to help Jake catch the episode's titular villain, named for all the Pontiacs he's stolen. Of course, by the end of the episode, we learn Judy is the Pontiac Bandit. Most Judy episodes unfold similarly. Usually, Judy manipulates Jake to help him solve a problem, like when he stages a hostage situation in season 5's "The Negotiation" to get Jake involved when a drug dealer is threatening to kill him. The clever thief usually finds a way to help the good guys and himself, all while escaping with a tidy sum. One of the only times he doesn't even attempt an escape is season 7's "The Takeback." Judy invites Jake to his bachelor party, forcing Peralta to arrest Judy's friends when he finds out they're stealing. Jake thinks the arrests end his friendship with Judy, only for his frenemy to appear and reveal he wanted Peralta to arrest the crooks because his fiancee doesn't want them at their wedding.

On top of all that, Jake and Doug have a penchant for loud duets, like belting out Paula Abdul's "Opposites Attract" in the interrogation room at the end of "The Takedown" or when a pre-recorded version of Judy covers 4 Non Blondes' "What's Up?" with Jake at the end of "The Negotiation."

In "Chocolate Milk," we meet Captain Holt's nemesis, Deputy Chief Madeline Wuntch (Kyra Sedgwick). Wuntch comes to the Nine-Nine for an inspection, and she happily fails the precinct. The reasons for the grudge are a little murky. Holt believes it's because that in 1989, when they worked closely together, he refused her sexual advances. But when they confront each other about it, a whole bunch of other details are unearthed, including Wuntch shooting Holt, Holt trying to get Wuntch kicked off the force in retaliation, and some kind of undefined embarrassment involving a run-in with Derek Jeter.

Wuntch proves a thorn in Holt's side for much of the series, inspiring an impressive list of insults on Holt's part (some of the best include "fork-tongued lizard witch," "she-skunk" and "coffin cave mold beetle"). Wuntch constantly uses her superior rank to either transfer Holt out of the Nine-Nine or to demote him, though usually Holt and his squad are able to outsmart the captain's old enemy.

In season 7's "Ding Dong," Wuntch dies unexpectedly, and yet even in death, she tries ruin Holt. A lawyer gives Holt a video in which Wuntch says she wants Holt to deliver her eulogy because she knows he'll fill it with crude insults and the ensuing scandal will decimate his career. It all ends up being part of a complex plot involving Wuntch's nephew, Adam (Michael McDonald), though with a little help, Holt gets through the event without causing a scandal. 

Considering Charles Boyle's strange, often unattractive quirks, when you look at the series as a whole, his luck with women isn't all that bad, though his decision-making skills could certainly use a tune-up.

For most of the first season, Boyle holds a fierce torch for Detective Rosa Diaz (Stephanie Alvizuri), but he never seems to have a real chance with her. In "The Party," Boyle falls hard for Vivian Ludley (Marilu Henner), the author of one of his favorite books, Stone Fruits and Stone-stones: Foods of the Paleolithic Era. The pair get engaged, but things start to turn sour when Vivian reveals she wants to move to Canada for her work. In the season 1 finale, they break up when Boyle is honest about not wanting to move, and later, we find Boyle and Gina (Chelsea Peretti) in bed together. They carry on a no-strings relationship for a while, though eventually they both decide it's best they end it. 

Boyle finally strikes gold in season 3's "Boyle's Hunch." There's immediate chemistry between Charles and art gallery owner Genevieve (Mary Lynn Rajskub), but shortly after they meet, she's convicted of robbing her own gallery for the insurance pay-off. Convinced she's been framed, Charles and Jake investigate her ex-boyfriend, but instead, they learn it was his jealous assistant. After she's freed from prison, Genevieve and Boyle become a couple, eventually adopting the young Latvian boy Nikolaj, whose name Boyle doesn't think anyone can pronounce, even though they say it just like he does.

Adrian Pimento (Jason Mantzoukas) returns to the precinct in season 3 after years of undercover work. Rosa is immediately wary of Pimento, noting that she's attracted to him and men she's attracted to are almost always freaks. 

Rosa's instincts prove to be on target. It's soon clear to everyone that Pimento is deeply scarred from his time undercover. His dialogue is often filled with bizarre and violent stories, including torturing and murdering victims while undercover, not to mention his intense drug use. Among some of his loonier actions in the show, there's when he breaks into Boyle's home after a year in hiding because he wants to clean up before seeing Rosa, taking the money Holt loaned him to get a private investigator license to bet on a dog show, and the time where he offers to let Rosa and Jake beat him up to fool a dirty cop, telling them, "You can punch me, kick me, pull my hair. I am a-okay being stabbed. Biting and scratching are on the table. You can use fire." 

The last time we see Adrian is in season 7's "Pimemento," when he experiences severe memory loss. Like the character from Memento, he tattoos important messages on his body, though some of them — like "buy toilet paper!!!" — seem less relevant. Jake and Charles eventually realize Pimento's been drugged by the vengeful Dr. Jones (Jim Rash), and his memory soon returns. 

After Rosa breaks up with Adrian Pimento in season 4, her romantic life turns down a different path. In season 5's "99," after the squad goes to LA for the funeral of Captain McGinty, Rosa comes out as bisexual to Charles, though she doesn't do it purely out of trust. During the trip back to Brooklyn, Boyle gets nosy about Rosa's love life and eventually catches her making a phone call to a woman. She comes out to the rest of the squad in the following episode, once it's clear that expecting Boyle to keep a secret is ridiculous.

While the squad is perfectly accepting of Rosa, her parents are a different story. Oscar Diaz (Danny Trejo) and his wife, Julia (Olga Merediz), seem in denial at first over their daughter's coming out. They try to brush it off by reasoning that since she's still attracted to men, she'll eventually get married to a man and have kids with him. When she insists that might not happen, things get ugly. A few days later, her father shows up at the Nine-Nine to say he still loves her and accepts her, even if he doesn't understand. Julia is a different story. Rosa and her mother don't speak for a year, but Julia finally reconnects with her daughter in season 6's "The Crime Scene."   

For over five seasons, the squad's civilian administrator, Gina Linetti, is the undisputed mean queen of Brooklyn Nine-Nine. She offers sometimes surprisingly wise advice to her coworkers, albeit usually through mockery, and that's only when she bothers to acknowledge them at all. Gina spends most of her time in the office on her smartphone, flirts shamelessly with the married Terry, and takes very little seriously. Of the things she does take seriously, there's her hilarious dance work with troupes like "Floor-gasm" and "Dance-y Reagan." 

But in season 6, Gina decides it's time the squad look to someone else for their interpretive dance and cruel one-liners. In "The Tattler," Gina confides with Jake that she's decided to leave the Nine-Nine, and the following episode, "Four Movements," is her final appearance as a series regular. However, she comes back for "Return of the King," having become a successful self-help celebrity by turning her obnoxious nuggets of "wisdom" — like "no one knows you can't take it with you; be buried with your money" — into what she calls "Gina-mandments."

In the season 6 finale, Acting Commissioner Madeline Wuntch gets the best revenge she'll live to get on Raymond Holt. At the end of the episode, Holt reveals that because he was only a patrolman for a month before being promoted to detective, Wuntch has decided to correct the situation by making him serve out the required time as a patrolman. The season 6 finale ends with Holt directing traffic.

Neither Holt nor the squad have an easy time getting used to the demotion. In the season 7 premiere, during a city-wide manhunt for a would-be assassin, Holt can't seem to get out of captain mode and take orders rather than give them. In "Captain Kim," the squad ends up driving away Holt's replacement, Captain Julie Kim (Nicole Bilderback), when they wrongly believe she's there as Wuntch's plant. It doesn't help matters when Holt's unstable new partner, Debbie (Vanessa Bayer), steals cocaine and guns from the precinct's evidence locker and tries to sell them to dangerous drug dealers.

Fortunately, the squad doesn't have to bear Holt as a patrolman long. When Wuntch dies in "Ding Dong," her death undoes Holt's demotion, and the Nine-Nine gets its captain back.