Fans of Brooklyn Nine-Nine are patiently waiting for the seventh season. Everyone who loves this show definitely has their favorite character, but we also all can’t help but love Captain Raymond Holt. His character is certainly dynamic, funny, and totally endearing. You may think he would make for the best boss ever, he certainly has his redeeming moments. However, every boss also has their downfalls. In case you need a refresher, here are 5 times Holt was the best boss ever, and 5 times he was the worst.
Worst: Everything with Madeleine Wuntch
Remember when he involves himself in Jake’s case because he thinks that he’ll mess it up? This woman grinds Holt’s gears so much that we’re certain he would throw every one of his detectives under the bus to get the best of her. He loses all faith in them, specifically Jake, when it comes to Madeleine Wuntch. That’s not super cool, and this woman definitely brings out the worst parts of Captain Holt, especially when it comes to being a boss.
Best: The Halloween Heists
While Captain Holt has quite the tough exterior, it is always hilarious when he lets loose and participates in the shenanigans of the precinct. Specifically, he’s a pretty stellar boss when it comes to the Halloween Heist.
Yes, Holt becomes super conniving and back-stabbing because he’s super competitive, but this is definitely something a cool and amazing boss would participate in. His enthusiasm makes him pretty awesome.
Worst: When He Ruins The Beach House
We all definitely felt bad for Captain Holt during this episode. The gang is headed to Charles’s ex-wife’s beach house, and Jake begrudgingly invites Captain Holt after realizing that Holt has never been inviting to a precinct outing because of his sexuality. Of course, we pity him, but he certainly doesn’t gain any ‘cool boss’ points in this episode. He spends the entire episode being quite the Debbie-downer, and that doesn’t suit his ‘good boss’ persona very well.
Best: When He Helps Rosa Break Up With His Nephew
Not only is Captain Holt totally supportive of his nephew, Marcus, dating his employee, Rosa, but he even invites them over to his house for supper. What makes Holt an even better boss, is that Rosa confides in him that she actually wants to break up with Marcus. Rather than getting angry, Holt actually helps Rosa break it off with his nephew. If that isn’t some incredible boss-employee relationship, we’re not sure what is.
Worst: When He Thinks He’s Better Than Gina
This is probably one of Holt’s least redeeming moments. You’ll remember when Gina and Captain Holt take psychiatric evaluations, and they end up getting the same score. This offends Holt, because he thinks he’s better than Gina. While he doesn’t say it out loud, Gina knows that Holt thinks of her as an inferior. This is super not cool, because no boss should think they’re exceptionally better than any of their employees. Obviously, Holt redeems himself, but this was definitely not his best moment.
Best: When He Loans Pimento Money
After Pimento is having a difficult time sorting out his life, Holt offers to lend him $2,000 to help him get a Private Investigator’s license. That’s a pretty generous offer to make to a previous employee, and this definitely proves that Holt has a heart of gold, and treats his employees incredibly well. Yes, Adrian gambles this away on a dog show, but it’s the thought that counts, right?
Worst: When He Doesn’t Help Terry Report Racial Profiling
This is an incredibly deep episode. Terry experiences racial profiling by a fellow officer when he’s off the clock, and wants to file a complaint. Captain Holt believes it will only jeopardize Terry’s career, and refuses to submit the report. The two work it out, and Holt explains it’s because he himself has faced a lot of repercussions for being a black man. However, he always should have had Terry’s back, because all he wanted was support from his boss.
Best: When He Tries to Get Amy Mad
This sounds like this is a “bad boss” thing to do, but it really isn’t. Holt is keenly aware that Amy will never do anything to cross him. Rather than exploiting this loyalty, Captain Holt tries to get her to stand up for herself in front of him.
Holt loses Amy’s favorite pen, and she claims it’s okay, but Holt tries to get her to express her true anger over the situation. Holt wants Amy to show her backbone, and this is actually a really impressive part of Holt’s leadership.
Worst: When He Relapses Into a Gambling Addiction
You’ll remember when Jake, Holt, and Terry must work together to infiltrate an underground gambling ring. While Jake is the one to go undercover, it’s because they realize that Holt has A LOT of unresolved gambling problems. His addiction definitely comes to the forefront, and it gets pretty ugly when he starts snapping at Terry and Jake. Yeah, it’s kind of funny, and it works out in the end, but Jake and Terry certainly had to take on the ‘boss’ position during this situation.
Best: When He Jeopardizes Himself for Rosa and Jake
After Jake and Rosa find themselves framed and in jail, Holt’s only hope of getting them released is to ask Seamus Murphy (a mob boss) for any details he has about the framing. Murphy agrees to help, but only if Holt “owes him a favor” in the future. This is scary stuff, and certainly should not be taken lightly, but Holt agrees in order to help his detectives. In fact, he doesn’t even tell anyone that he made this deal, he simply sacrifices himself for Jake and Rosa. That’s some pretty deep stuff, and proves that Captain Holt is probably one of the best bosses a person could have.
