The 10 Deadliest Characters From Brooklyn Nine-Nine

More than just your average cop show, Brooklyn Nine Nine has captured the hearts of audience members far and wide through its unique blend of comedy, sentimentality, endearing characters and confrontation of real world issues. Perhaps this is what lead to the series' Season 7 renewal at NBC.

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While hosting such broad range of positive traits, one cannot forget that this is still a cop show, and one of the prerequisites of this this genre would be high-octane action and dangerous characters. Brooklyn Nine-Nine has bucketloads of both, with deadly characters on both sides of the law using their skillsets for both evil and justice.

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Dean Winters as The Vulture in Brooklyn Nine Nine
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10 Keith Pembroke (The Vulture)

Dean Winters as The Vulture in Brooklyn Nine Nine

While more of a jerk than anything else, "The Vulture" gets a place on this list due to the internal havoc that he has caused for the 99 on numerous occasions. He has stolen Jake Peralta's cases several times, threatened to get Terry Jeffords fired as he confronted him while tackling a hostage situation, and generally mistreats the officers in the 99th Precinct.

Probably his most harmful actions against the 99 came when "The Vulture" took over as Captain of the 99th Precinct during Raymond Holt's temporary absence. During this time, he demoted Jake, commanded Jake and Amy to cease their relationship and forced the squad to only pursue minor cases due to entering into a bet with another captain over who could make the most arrests.

9 Madeline Wuntch

Like "the Vulture", Wuntch is also a member of the NYPD and a longstanding nemesis of Captain Raymond Holt. While their rivalry started many years prior, Wuntch has continued to cause issues for Holt and the 99, using her position of authority to quash the squad's efforts to succeed.

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Some of her most harmful actions against the 99th precinct include initially rejecting Holt's application for more money to assemble a task force to tackle a drug, and giving Holt an ultimatum in which he had to leave his position as Captain of the 99th Precinct.

8 Seamus Murphy

Murphy, the head of an infamously brutal New York crime family, managed to blackmail the squad from the 99 at a time when they were particularly vulnerable. He offered Amy Santiago critical information that could save Jake Peralta from legal troubles in exchange for a favour, and while Raymond Holt convinced her to turn him down, he later took the deal himself.

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This deal led to Holt being indebted to Murphy, and due to not adequately repaying his debt, Murphy threatened the life of Kevin, which lead to Kevin being hidden in a safe house with the team working overtime to protect him from harm.

7 Raymond Holt

The fearless Captain of the 99th Precinct, Raymond Holt has put his dignity, career, and even his life on the line to protect his squad and his loved ones and to take down some of the most notorious criminals in New York City. When notorious dirty cop Melanie Hawkins was on the verge of getting Jake Peralta imprisoned, Holt struck a deal with the devil in the form of Seamus Murphy in order to save Peralta, thereby putting himself in the firing line. Following the decision, he also played a part in taking down Murphy.

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In what was a brave and chivalrous decision, Holt once decided to leave his job at the 99 to prevent Wuntch from transferring his squad, thus saving their jobs. This was also a temporary issue, however, as Holt returned to the 99th Precinct stronger than ever. Holt has proven that he is not one to be messed with, particularly when it comes to his loved ones.

6 Jimmy "The Butcher" Figgis

One of the most deadly mob bosses around, Adrien Pimento went paranoid after working as an undercover operative for him for 12 years, after doing a series of violent and gory tasks. Soon after the conclusion of Pimento's undercover operation, the unforgiving Figgis hired a hitman to kill Pimento, whereby Figgis requested Pimento's tongue and a photo of his dead body as proof of his death.

If such actions were not enough to prove his deadliness, Figgis also hired numerous moles in the FBI and threatened to kill Captain Holt and Detective Peralta with an intimidating phone call, resulting in the two police officers having to go into witness protection for several months.

5 Amy Santiago

While she may seem sweet and nerdy on the outside, Amy if a fearless former detective of the 99th Precinct who rose to the rank of sergeant and now heads up the department of uniformed officers downstairs. From the moment she did her double tuck, Amy has looked out for and come to the rescue of her husband Jake as well as her colleagues and friends, taking out some of the biggest and baddest criminals around in the process.

Amy mobilised the 99 to come to the rescue of Captain Holt and Jake when they were in hiding in Florida due to the threat of Jimmy Figgis, and she even took down the elusive killer, the "White Whale", as well as another assailant while wearing a wedding dress.

4 Bob Annderson

This seasoned FBI agent proved himself to be a dangerous foe on both sides of the law. He was an invaluable asset to the FBI, and tracked down a Mexican cartel for 14 years. Furthermore, he was a friend of Captain Holt from the past whom Holt was excited to team up with for an important mission involving Jimmy Figgis.

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Unfortunately, Annderson became a mole in the FBI for Figgis and double crossed Holt and the 99, taking Holt as hostage and nearly managing to murder him. It eventually took the wit of the entire squad from the 99th Precinct to outwit Annderson into giving up enough evidence for him to be arrested.

3 Rosa Diaz

Easily the most feared detective in Brooklyn's 99th Precinct, Rosa has led many important missions for the NYPD, including heading up an undercover task force for tackling a dangerous drug and using her apartment as a base for luring Bob Annderson into a trap; she even received an offer for promotion to a New Jersey precinct searly on in the series.

While she may be famous for one-liners such as "What kind of woman doesn't own an ax?"as well as her interest in men such as Adrien Pimento who reflect her lust for danger, she also poses danger in another sense, namely by being a support pillar for her colleagues that no criminal in their right mind would ever want to be pitted against.

2 Adrien Pimento

While Rosa may be intimidating, the trait that Pimento displays that is unique to the rest of the 99 is his all-out insanity. This is due to his 12 years of undercover work inside the mob, where he was forced to carry out numerous bloody and gory tasks in order to maintain his cover. In fact, Pimento suffered from a serious identity crisis upon returning to the NYPD, which is why he left soon after returning and unsuccessfully took on numerous other jobs.

While he does suffer from a serious condition, he remains a dedicated member of the NYPD, and is an effective and fearless detective with a flair for combat.

1 Melanie Hawkins

This formidable foe proved to be a master tactician on both sides of the law. As an officer in the NYPD, Lieutenant Melanie Hawkins was a widely respected leader of an undercover task force; a role which saw her become a role model to both Jake Peralta and Rosa Diaz. Unknown to the detectives from the 99, however, Hawkin's undercover squad were really the "Golden Gang" bank robbers, who had evaded capture from the authorities.

Once Peralta and Diaz learned of her successful criminal activities, they attempted to lure her into a trap, only for Hawkins to outsmart them and frame them for the "Golden Gang" robberies. It eventually took a favour from Seamus Murphy to bring Hawkins to justice, and prevent her from ruining the lives and careers of some of the 99's finest.

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