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Brooklyn Nine-Nine might have been a comedy, but the 99th Precinct got its share of troublemakers. From astute criminals to dirty cops and insufferable coworkers, such characters were always pushing the squad to its wit's end, patience, and even their liberty. Some, such as Doug Judy, were charming scoundrels whose actions kept the precinct in constant suspension, while others, such as Melanie Hawkins and Seamus Murphy, turned out to be seriously sinister threats.
The squad also dealt with internal nuisances, like the egotistical Vulture and the completely incompetent C.J. Stentley, both of whom made everyday policing a nightmare. Whether they were stealing cases, betraying their allies, or forcing the team into hiding, each of these characters left a lasting mark on the 99.
Despite the chaos they caused, these troublemakers gave us some of the most intense, hilarious, and unforgettable moments in the show’s history. Their clashes with the squad added drama, comedy, and excitement to the precinct’s adventures. Here’s a look at 10 characters who gave the 99th Precinct the most trouble—some in ways they never saw coming.
1. Doug Judy (Pontiac Bandit)
Doug Judy, the Pontiac Bandit, was a one-man thorn in Jake Peralta's side. A smooth-talking, R&B-loving car thief who consistently outwitted the precinct, Doug enjoyed an unlikely friendship with Jake. Even though he was a criminal, his charm and sense of humor made him one of Brooklyn Nine-Nine's most enjoyable troublemakers. Doug's skill at working situations to his advantage annoyed Jake, but his presence was always good for a thrilling chase. His ultimate escape cemented him as one of the series' best villains.
2. The Vulture (Keith Pembroke)
Detective Pembroke, aka "The Vulture," was notorious for appearing at the last minute to steal credit for the efforts of other detectives. His arrogance and lack of integrity made him universally hated among the unit. Later, his promotion to Captain only served to make things worse, as his ineptitude resulted in bad leadership choices. Whether pilfering cases or making life hell for his fellow officers, the Vulture was one of the most annoying characters to ever set foot in the 99th Precinct.
3. Madeline Wuntch
Madeline Wuntch, Captain Holt's long-time arch-nemesis, was an expert at manipulation and office politics. She constantly held back Holt's career, using her administrative authority to thwart him every chance she got. Their feud created some of the show's most wickedly petty confrontations. Even in death, Wuntch's legacy remained, a testament to how much havoc she wreaked. Her skill at manipulating the system against the squad made her one of the precinct's greatest adversaries.
4. Adrian Pimento
Adrian Pimento, an ex-undercover detective, was mad because of the time spent in the mob. His drastic mood swings paired up with paranoia were such an explosive combination that he turned into one dangerous asset who left ruin in his footsteps. Whether it's through sabotaging investigations or creating on-the-job personal drama, chaos came from Pimento's instability. Even when doing so with the best intentions, he remained one of the precinct's biggest problems.
5. C.J. Stentley
A temporary precinct commander, C.J. Stentley proved to us that the ineptness is a clearer destructor than outright corruption. He simply could not lead, and the results were disastrous. Too afraid to make tough decisions, he allowed others to cover up his mistakes, a weakness that only angered the team all the more. Not so much evil-well, maybe just a tad. He surely ranks as one of the most annoying sons-of-a-gun the 99th has had to work with.
6. Figgis
The fearsome mobster Jimmy Figgis was after Jake and Holt and takes it upon himself to send them into witness protection. His criminal empire made him the most dangerous opponent that had ever been thrown at the squad. Just to take him down required a lot of serious undercover work, upping the ante for the usually comedic show. Figgis' influence ran like a strong undertow affecting the squad far beyond the shores of his immediate presence, which made him one of their formidable enemies.
7. Trevor Podolski
Trevor Podolski was the son of Deputy Commissioner who was caught by Jake and Captain Holt for vandalizing police cars. He was arrogant, and his privilege was made apparent when it was revealed that he was not committing the crime for the very first time but was a repeated offender. This character used nepotism to get away with his crimes because his father kept bailing him out. Rather than being held accountable, he flaunted his immunity because of his dad's power. Though ultimately arrested by Jake with Captain Holt's support, Podolski’s actions exposed the dark side of nepotism, making him one of the show’s most unsettling antagonists.
8. Seamus Murphy
Seamus Murphy was a brutal crime boss who blackmails Captain Holt into performing favors for him. His cunning manipulation and knowledge of the loopholes of law made him a dangerous enemy. Murphy's threats were always perilous to the rest of the squad; they forced the squad into morally questionable situations. Unlike most criminals, instead of physical prowess, he used his power to stay in command; he was a far-off adversary to 99th precint.
9. Bob Anderson
Bob Anderson first seemed like a friend but turned out to be Jimmy Figgis's man. His deception was the most surprising twist in the series since he got the entire team into danger. As compared to other antagonists, Anderson's betrayal stung more because he was trusted. His skill to deceive people into thinking that he was in their corner made him one of the most dangerous troublemakers in Brooklyn Nine-Nine.
10. Melanie Hawkins
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Lieutenant Melanie Hawkins was a dirty cop who operated an illegal crime syndicate while having a heroic public image. She sets up Jake and Rosa for robbery, which created one of the series' most gripping story arcs. Her authority within the system enabled her to control situations in her own best interests, making her one of the series' most formidable characters. Her ultimate fall was gratifying, but the harm she inflicted solidifies her as one of the worst agitators the 99th precint ever had to deal with.
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