Comparing and contrasting Robby's interactions with Samira vs Whitaker as he spirals further and further downward and out of control is just so much more interesting to me when you take the genders of everyone involved out of it for a second. And I'm not saying that criticisms of Robby as someone with misogynistic biases are completely unfounded or unworthy of discussion, but there is also just so much more there.
It is abundantly clear that Robby sees Samira as a younger, less broken reflection of himself, as has been discussed in great length by people who are far more articulate than I will ever be. But I also see so many people arguing that Robby sees Whitaker through the same lens, so why isn't he treated the same way? And I actually so vehemently disagree with that interpretation, at least in so far as this season goes. I don't think Robby particularly sees himself in Whitaker, I think he feels seen by Whitaker, in more ways than one, and that is the crux of where Robby's attitude towards them differs.
The more Robby's self-loathing manifests, the more critical he becomes of Samira, and seemingly the tighter he attempts to draw Whitaker into his life. Abbot compliments Al Hashimi and says they'll be fine without him, accidentally hitting on Robby's biggest insecurity, and Robby immediately goes to offer Whitaker his house. Samira has a panic attack, so identical to the one Robby still hates himself for, and Robby introduces Whitaker to his motorcycle mentor and tells him how much he trusts him. And I don't see either of these actions as really about Whitaker personally or professionally, but rather what he represents to Robby. Someone who saw him at his weakest moment, guarded his most shameful secret, and still looks up to him as a respected teacher anyway; Someone who makes Robby feel like he isn't the catastrophic failure he views himself as.
Robby is suicidal. Perhaps at the start of the shift it was a more passive ideation, but as the hours drag on he's becoming becoming firmer and firmer in his convictions. And in this, keeping Whitaker close provides him both comfort in feeling seen in his final moments and the belief that he's tying up all his loose ends, that Whitaker will remain quiet and loyal inside the box he's tightly enclosing around himself--something that is inevitably going to blow up in both of their faces.
