Leland Stottlemeyer is kind of comically heteromasculine in his gender performance. It is even made fun of in s4ep4 Mr Monk Goes to the Office, when Leland is chewing on a toothpick, and Monk finds the perpetrator's toothpick, which he has chewed on, and hypothesises (which by show logic means he is correct) that the episode's bad guy, and implicitly, Leland, are "insecure." They are "always trying to impress people."
I don't know if this is going to be coherent. But physically, he is a broad-shouldered, mustachioed, serious-looking older man. He is physically strong and carries himself like he is in charge, and he has to because he is a police captain. He rides a motorcycle (offscreen), and sometimes he wears a leather jacket to impress women. He used to have anger issues, was too involved in his kids being winners (baseball), and he loves to grill, and he loves football (going to a game is better than sex).
But he is insecure. Early on in the show, he was insecure about Monk's superior detective skills, which is partly why he was so annoyed with him (that and their personal history). This insecurity does arguably not totally go away, because when Monk tries to warn him about Linda, Leland is mean and accuses Monk of being jealous because he does not have a badge. Yes, Monk wants his badge back, but you could say that this is Leland projecting his insecurities about his own work. He may not be as good as Monk, but at least he has a badge.
Also, he is insecure in his relationship with Karen. They are high school sweethearts with nothing in common except for their love and their children. And in the episode where one of their kids play baseball, Leland and her both agree that their children should be da best. But he is insecure here, and it fuels his anger issues. He feels emasculated because Karen stops touching him, and he fears she is cheating on him.
One could also argue that he is insecure in his relationship with Linda because of his failed marriage. She is arguably a way for him to regain his masculinity after what he went through with Karen, and that is why he takes her betrayal so, so hard (who wouldn't feel betrayed), that's why he lashes out so harshly at Monk. As I noted above, Leland calls Monk out for his lack of a badge, but he also points out that Monk does not have a woman. He is attacking Monk's presumed heteromasculinity here. Leland is A man. Monk is jealous of that. It's Leland projecting with some amount of truth in his words, because, yes, Monk wants his badge, and he misses Trudy, but he is not Leland.
Leland is also insecure when it comes to TK. He fears that he will die alone; he needs a woman, so he rushes in. His old man running into a relationship comes from feeling that he has to be with someone, and those feelings come from expectations that are created by heteronormativity, and fullfilling these expectations, is him completeting this heteromasculine image he wants to have of himself.
Leland knows who he feels he has to be, and he shows that in the way he appears to others, but it all stems from insecurities brought on by basically heteronormativity. He has to conform. He has to be hypermasculine. He has to chew on his toothpicks.
And yet, to him, Monk is "the man" despite not being hypermasculine. Leland calls him "fragile" at some point; he knows he has to cater to Monk and has to take care of him. Yet, Monk is "the man." It's because Monk is a great detective, sure, but he may also be "the man" because he is himself. He is someone who does not conform to rules Leland feels he has to follow.
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