Captain Raymond Holt remains to be the 99th Precinct's captain, but the station has had a string of other leaders in Brooklynn Nine-Nine's 7 seasons.
The 99th Precinct has had numerous captains in Brooklyn Nine-Nine. Over the years, the titular station in the Fox-turned-NBC sitcom has gotten several chief officers. Each one of them had varying serving time, not to mention different rapports with the rest of the squad. At the end of the day, their respective stints make the team and the viewers more confident that Captain Raymond Holt (Andre Braugher) is the best one for the job.
The events of Brooklyn Nine-Nine was kicked off when the no-nonsense and stoic Captain Holt became the precinct's leader. Initially, some members of the squad had a hard time gauging what his leadership style will be, especially since he cannot be more different than their previous commanding officer. Jake Peralta (Andy Samberg), in particular, butted heads with him. Through time and experiences, they all developed genuine concern and friendship for each other.
Holt has primarily been the captain of the station in Brooklyn Nine-Nine's seven seasons thus far, but in several instances, he's replaced by a different commanding officer. Here are all the captains the 99th Precinct has had in the sitcom.
In Brooklyn Nine-Nine season 1, Holt was transferred to the station to replace the team's old boss, Captain McGinley, (Michael G. Hagerty) who had retired. McGinley's ineptitude and passive attitude enabled Jake's childish antics, making it difficult for the effective, but silly detective to adjust to Captain Holt's leadership style. It's also safe to assume that it was during McGinley's stint that Norm Scully (Joel McKinnon Miller) and Michael Hitchcock (Dirk Blocker) started really slacking with their work, leading to what they've become in the series. Later in season 5, episode 9 titled "99," McGinley is revealed to have died. To pay their respects to their former boss, the whole squad including Captain Holt traveled to Los Angeles to attend his funeral.
Given McGinley's style of leadership at the 99th Precinct, it made sense that the NYPD replaced him with the efficient and no-non-sense captain Raymond Holt. Known for not showing emotions, it took a while for the team to gauge their new commanding officer since he's difficult to read. Despite his strict demeanor, Holt is a smart and fair boss, which makes him a good fit for the talented detectives at the station.
As Peralta and the rest of the detectives knew Holt better, they became more respectful and receptive of his leadership style in the station. On the flip side, Holt became more open to his subordinates, even joining some of their hilarious antics. This is also the reason why even during the brief times that Holt was briefly out of his post as the 99th Precinct's captain in Brooklyn Nine-Nine's seven seasons, his people still treated him as their leader.
At the end of Brooklyn Nine-Nine season 2, Raymond Holt's arch-nemesis Madeline Wuntch (Kyra Sedgwick) forced him out of the 99th Precinct by promoting him to become the Head of Public Relations of the NYPD. This left the station without any commanding officer until it's announced in the season 3 premiere that Seth Dozerman will take Holt's place. Played by guest star Bill Hader, the character's stint in the precinct and the show, in general, didn't last very long. During his introductory speech, he passed out due to his genetic heart condition which lowered his life expectancy. He bounced back after that, but when he caught Jake and Amy (Melissa Fumero) in the storage room kissing, he suffered from a heart attack, leading to his eventual death. Overall, he was only captain of the 99th Precinct for two days.
On the heels of Captain Seth Dozerman's death, the station was once again left without any commanding officer, leading to Keith Pembroke's appointment in Brooklyn Nine-Nine season 3. Most famously known as the Vulture, the character is played by Dean Winters. Prior to becoming the station's captain, Pembroke already had a bad history with the precinct as he used to take over the detectives' cases after they laid the groundwork for them. It also didn't help that he's extremely obnoxious and annoying. Regardless, Jake tried to cozy up with Pembroke; unfortunately, this backfired after the new captain forbade him and Amy from being in a relationship.
After few more episodes of Pembroke at the helm, Holt finally reclaimed his position as the 99th Precinct captain in the Brooklyn Nine-Nine season 3, episode 4 titled "The Oolong Slayer." That said, he returned to the show a few more times with his last appearance in the season 6 finale titled "The Suicide Squad."
During Jake and Captain Holt's time in Florida, while they were in witness protection, the 99th Precinct got a new leader: Jason C.J. Stentley. The character portrayed by Ken Marino was introduced in Brooklyn Nine-Nine season 4, episode 2 titled "Coral Palms Pt. 2" during the team's regular morning briefings. Weirdly, CJ knows that his hilariously unqualified for the job. When asked how he's able to rise through the ranks at the NYPD, he chalked it all up to luck. Apparently, he was supposed to go to a dentist appointment but got the location of the clinic wrong. There was an ongoing drug bust in the wrong place where he accidentally tripped the kingpin. He was given credit for the successful operation and was promoted shortly after that.
To make up for his lack of qualifications, he catered to the squad's every want to keep them happy and motivated. Some of the officers and Gina (Chelsea Peretti) enjoyed this, but they eventually realized that they want Holt back as their leader. CJ appeared a few more after he's booted out of the station, his latest outing was in Brooklyn Nine-Nine's season 6 finale like the Vulture where they helped Jake and the team take down NYPD Commissioner John Kelly's (Phil Reeves).
At the end of Brooklyn Nine-Nine season 6, Madeline Wuntch, who became the temporary NYPD Commissioner following John Kelly ousting, forced Captain Holt again from the 99th Precinct. This time, she demoted him to a beat cop upon learning that he didn't serve enough time as a uniformed officer before being promoted as a detective. This led to the introduction of Captain Julie Kim (Nicole Bilderback) who took over his job at the station.
At first, Captain Kim seemed to be the ideal candidate to replace Holt at the Nine-Nine — she's the first Asian-American female captain in the NYPD and has a penchant for charity. She also put a genuine interest in the detectives. Despite this, something just didn't sit right with Jake about her, so he started investigating her. It turns out, she was not in cahoots with Wuntch, as Jake assumed. In fact, the only reason why she really wanted to work at the 99th Precinct was because she's such a fan of Holt. She didn't want to say something about this initially because Holt was already devastated about his demotion.
