To be perfectly honest, Brooklyn Nine-Nine would have been an amazingly progressive show even if Captain Holt's character was excluded. However, the presence of a gay black man as one of the lead roles in a sitcom (which makes it a point to discuss both sexuality and race issues), is why this show is unprecedented in so many ways.
Captain Holt's robotic obedience to customs and laws are only surpassed by his expectations of fairness from his squad. While he tries to let them handle their problems as best they can, he does step in when things take a turn for the worse (but also unwittingly becomes the actual problem in several instances.)
10 Overrated: His Emotional Stability
Captain Holt is best known for his stoic demeanor to most things, rarely even raising his eyebrows let alone hinting at a smile. Though he is generally able to pull this off, there are times when he has no idea how ridiculously cranky he is being.
For instance, after getting stabbed during a mugging, he doesn't tell anyone about it but instead takes his impotent anger out on the nine-nine. When the squad goes to Charles' alimony beach house, Holt gate-crashes the party (courtesy Jake), and just sulks his way through the night, oblivious to how miserable the others are.
9 Underrated: His Eternal Feud With Wuntch
Madeline Wuntch is the Joker to Holt's Batman, or so he goes around telling everyone. In addition to his complete lack of trust in her, regardless of her intentions towards him, a good chunk of the show's humor comes from their interactions together — the best, of course, being his hilariously terrible insults for her.
The feud is eternal because it apparently lasts after her death, as shown when she tries to humiliate him at her funeral (which he is asked to officiate because of his "close relationship" with her.) Holt wins the final round, but he admits that he will miss Madeline deeply.
8 Overrated: His Greatest Case
Raymond Holt's proudest moment, excluding his marriage to Kevin and becoming an NYPD Captain, is his capture of the Disco Strangler, a seventies serial killer. The way he talks about it, however, sounds like he's reinvented the wheel. When the criminal escapes prison, everyone believes that he is killed in a vehicle fire, but Holt knows something else is up.
Instead of acting professionally, he harshly accuses the prison truck driver of having succumbed to the Disco Strangler's "groovy voodoo." While his hunch turns out to be unbelievably accurate, his obsession with the case is simply over the top.
7 Underrated: His Various Addictions
One would never think that a man as disciplined as Raymond Holt — someone who found entertainment in reading municipal code as a child — to suffer from extreme addictive tendencies.
The man is filled with surprises, indeed, like when he resumes his gambling habits while on an undercover job (denying vehemently that he has a problem until it gets serious.) In "Tactical Village", Gina accidentally gets Holt hooked on to Kwazy Kupcakes, to the point that he hides out in the men's room to avoid being labeled a hypocrite.
6 Overrated: He Needs To Win Everything
The Halloween Heists bring out something dark in Captain Holt, kind of like going through a personal Purge. No respect, no manners, no shame, nothing comes in the way of satisfying his craving for the final prize. He also pretends that he is the only "two-time champion," a patently false fact as one of them ends in a three-way tie.
Holt hates the idea of being wrong at anything, even innocent mathematical paradoxes like The Monty Hall Problem. When Amy admits to him that his solution is incorrect, as opposed to Kevin's, he tells her that she's fired.
5 Underrated: He Believes In His Officers
Eccentric or not, Captain Holt is a compassionate person who goes the extra mile for his officers' happiness and safety. During Amy's Thanksgiving, Pimento embarrassedly reveals that he has been fired from his job, but Holt immediately offers him the basic financial support needed to obtain a Private Investigator license.
When Amy's smoking is exposed, the captain insists on taking her out for a run to get the nicotine out of her system. Most importantly, Holt puts himself in grave danger after making a deal with an Irish mobster to get Rosa and Jake out of prison.
4 Overrated: His Taste In Music
It's a given that Holt's musical appreciation would be as ancient as his social and linguistic expectations from people. He refers to any kind of modern music as "noise", but places the Western Classical canon on a pedestal. His bizarre overreaction upon meeting John William Weichselbraun, some obscure oboist, is irrefutable evidence towards this.
In fact, he claims to have been removed from the musician's performance for "gasping too loudly." Holt tries in vain to get his subordinates interested in his aesthetic, for example, when he calls the composer, Gustav Mahler, the "original punk rocker."
3 Underrated: He Supports Queer Voices
Holt emerged from the closet in 1987 and has never looked back since. He is totally unashamed of his sexuality, irrespective of how often he was (and is) subjected to homophobia and bigotry. He has been busy improving the framework for queer people within the NYPD — it all started with the founding of the AAGLNYCPA decades ago.
More recently, Holt extends all his love and support when Rosa comes out as bisexual, telling her that "Every time someone steps up and says who they are, the world becomes a better, more interesting place."
2 Overrated: Does He Really Support BLM?
A volatile subject in current times, the BLM movement is vaguely alluded to in the episode "Moo Moo", in which Terry is racially profiled by a white cop for being out on his own street. After finding out that Terry is a cop, the offender apologizes specifically for that reason, obviously enraging the sergeant.
However, his attempt to submit a complaint regarding the matter is blocked by Captain Holt because the fallout might have a negative impact on Terry's career. Although he concedes that he was wrong to place professional security over the very real issue of police brutality, the fact that he hesitates in the first place is not encouraging.
1 Underrated: Best Workplace Daddy Ever!
When the series started, Jake found Holt's authoritarianism disagreeable, and consequently tried to rebel in all sorts of nonsensical ways. Over time their relationship has gotten much more intimate, with both of them unironically calling each other "son" and "dad".
When Jake's father disappoints him once again, Holt tells him that he's proud of him, bringing the former to tears. This paternal aura of his engulfs the entirety of the nine-nine, as seen when Amy accidentally says "Captain Dad is just my boss," stunning Rosa into silence.
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