Raymond Holt, the beloved Captain of the 99 and one of the funniest characters on Brooklyn Nine-Nine comes across as hard as nails — he expects work to be completed, on time, and in triplicate (if he could have his way.) He refuses to bargain over his moral standards, which is honestly one of the best traits to expect in a police officer, not even if his career is at stake.
As stentorian as he usually is, Holt does indulge in a lot of the shenanigans initiated by his squad, mostly Jake. However, there have been several moments in which the complexities of his life as a minority in terms of both race and sexuality, results in some rather unforeseen outcomes. A good number of his problems can be attributed to his inflexible nature, even in the face of solid logic.
10 Pretends To Be Stoic
To be fair, Captain Holt almost never exposes his feelings through facial expression (and every time he claims he does, nobody else is able to see it.) However, this detached demeanor is clearly a front for his internalized emotions, many of which are incredibly complex.
For instance, the fact that he has to deal with being a gay, black man in NYPD during the 70s and 80s have made him apathetic in many ways, partially explaining why he chooses to respond with aloofness rather than through emotional involvement: to protect himself.
9 Feud With Madeline Wuntch
A grown man; in fact, one of the most mature characters in the story, continuing a feud with his so-called nemesis for several decades is the definition of woeful. Holt won’t, or can’t, give up on hating Madeline Wuntch for something she did in the ancient past, nor can he find it in his heart to forgive her for it.
What’s sad is that he suspects foul play at her funeral, expecting her to have the last laugh from beyond the grave, forcing him to deliver his eulogy at a pretend funeral to not be caught unawares. That he’s proven to be right in the end doesn’t mitigate his ridiculous compulsion.
8 Denies His Obsessions
Captain Holt is a man of few interests, and whatever he likes most is as spartan as it can be. Tan is his favorite color and he has a single dream, annually appearing on “Tax Day.”
Interestingly, it seems that behind this bland exterior lies the heart of a manic addict. Holt gets obsessed with the game Kwazy Kupcakes, but flat-out denies it altogether until Gina makes him capitulate. He’s also shown to be a veteran gambler (and a terrible one to boot.) Even in this situation, he still refuses to acknowledge his faults.
7 His Victory Complex
Coming from a presumably strict family, Raymond Holt prides himself on his accomplishments in life (much like his latest protege, Amy Santiago.) The issue is that he goes overboard whenever the stakes are raised against him, as can be seen in all of the Halloween Heists.
This is one of the few situations in which Holt trash-talks, and he has broken into Jake and Amy’s apartment in the middle of the night just to prove a point. The man really needs to accept that failure is an option.
6 Acts Superior About His Tastes
Holt generally enjoys classical literature and music, which is not really problematic; his upbringing and cultural lineage have led his aesthetic in this direction. The facet of him that emerges when he encounters different forms of art, though, is nothing short of condescending.
Holt refers to “all music after Mahler” is basically noise, and rudely discards Terry’s version of his toy train set because it doesn’t match his hyper-specific vision. This kind of immature attitude in a superior officer is pretty pathetic.
5 Doesn’t Support Terry When He Gets Racially Profiled
In the singular episode to discuss racial profiling of African-Americans, Terry is racially profiled by a fellow officer who believes that he might be a criminal loitering around (just because he’s black.)
Although Captain Holt eventually takes his sergeant’s side and advises him to file a proper complaint, he tells Terry to let it go when he first hears about it. Discussing the probable outcomes of this situation would have at least been a start, rather than just forgetting that such an unjust act ever happened.
4 Snubs Anything He Doesn’t Understand
Captain Holt is a difficult man to read, but he’s just as impossible to relate to. This is mainly because he doesn’t take the effort of getting to know another person for who they are, and for what they do, but prefers to resort to catty remarks and cold observations instead.
For example, when Gina explains to him, in detail, how much dancing means to her, he dismisses it as “a hobby”, one which wouldn’t be able to pay the bills nor bring about personal growth. Holt assumes that he gets to decide how others live their lives, which is quite lamentable.
3 Tries To Handle Everything Alone
Captain Holt is blessed with a team that is intensely loyal, not to mention a loving husband who would move the world for him. And yet, he presumes that he should be capable of managing every situation without asking for assistance, even if he undergoes the horrifying experience of an attempted mugging and a successful stabbing.
Is this because Holt doesn’t trust people to take care of him when he’s down, whether physically or psychologically? Not telling Kevin of this event makes it that much more gloomy.
2 Fixation On “Proper” Syntax
Amy might be specific about proper word usage, but Holt’s reaction to alternative forms of grammar is downright egregious. In fact, he often appears confused when people mention his unnecessarily rigid definitions of language, indicating that he lacks the perspective to see beyond the one in which he still remains.
Holt has rejected potential employees for shortening “you” to “ya”, referred to the concept of “woke” as “awake”, and states that those who say “What’s Up?” are people “not worth talking to.” Sad is an understatement in this case.
1 A Vengeful Romantic Partner
When Raymond Holt was dating Frederick, one of his earlier boyfriends, the latter claimed that the relationship ended over an argument about a precious wooden duck belonging to the latter. He rejects Holt and Jake’s pleas, at least until his ex offers an apology for the error.
Until now, the story appears to be on the captain’s side, but at the conclusion, he explains that he is, in fact, responsible for the duck’s disappearance, except that it was tossed into a river due to its “weak beak.” So much for romantic stability.
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