I kinda zoned out at the end of last night's episode. What were the two paths Hugo was telling Kendall? I believe Kendall told Hugo to go down the path which I believe hurts his dad image correct?
The Hugo / Kendall conversation highlights the hard demarcation point between high level staff and analysts and actual blood family.
You don't get to say "No" to a certain level of power. It just doesn't happen. No matter how insane and ridiculous the situation becomes. In media optics, if you distill it down to fundamental crisis management, in that situation you give the person two "choices".
The one where they survive. And the one that they should never take if they have any sense of pure self preservation. It is not a real choice, it's an illusion of choice. If you closely watch the larger meetings on the show, the support staff like Gerri, Karl, Frank and even Tom don't actually try to get into direct confrontation with the adult children. Even if they are wrong. Even if they are behaving stupidly. They will however begin to undermine and snipe at each other. Only in a very rare moment of actual honesty, does Gerri tells Roman, when the attempt against Logan fails -
What's in this for me? How does doing this help me?
Otherwise she decides she has to indulge Roman's sexual advances and partially sate them. You begin to see that Gerri, Karl, Frank, Hugo, Karolina and Tom all had to navigate a very complex minefield to get where they are and stay where they are. And they see the children doing things and remaining anyway, that would have gotten anyone else either fired or just outright killed. Someone on the writing staff is a baseball fan, because Frank's character construction is shaded towards Joe Torre as a real life counterpart. Torre was known to have a deft ability to keep simple questions in play to manage Old Man Steinbrenner's gigantic ego and impulsivity.
The evolution of Kendall towards real character progression is that he finally understands that Hugo and Karolina are effectively telling him that there is no choice. There is only one real practical option. That's too run Logan's reputation into the ground even further, even after death.
Part of the reason that the writers pair off Tom and Cousin Greg so often is they swing between two worlds. Tom is both family and he's not. He married in but he's not real blood. Hence his sniveling and begging when he tells Logan that there might be a divorce. And he is basically asking for Logan's forgiveness and blessing. Tom has the same limitations of a Frank or Karl, but none of the benefits of an actual Roy child. Even Connor, the village idiot, is granted more leverage than Tom. Cousin Greg is family, but only serves a role as human punching bag. He also is inside and outside at the same time. Because he's incompetent, he has no role. Because he's technically blood, he has to be tolerated. Logan sees no value in Greg other than as a way to torture his inane gutless brother. You'll notice before "Boar On The Floor", that Cousin Greg rebels against Logan. He tells him that he told the truth and he wasn't supposed to be punished for the truth? What's the lesson there? With a malignant narcissist, and in a pit of vipers, trying to bunker up and huddle in only makes you a bigger target. What little safety you have is just to go on the full bore attack.
The reason Tom is so vicious to Greg is that Tom gets it on all sides. He takes the full brunt from Logan, then Shiv at home, then the adult Roy children who mock him, then the infighting that naturally occurs in the support staff. Tom cannot attack a real Roy with a role, so Greg is the closest thing possible. Thematically, to go after Logan after his death shows a stark reality within the show's world building - The only way out is to run over someone else. Living or dead doesn't matter. The carnage is going to happen eventually, all you can do is make sure it's not you. You can't wait for your moment, you must actively bear down on everyone else all the time. You are a hunter or you are prey.
A critical visual motif on the show is reflection with distance. You'll see Kendall staring into a window, barely seeing his reflection from afar, and struggling to look at himself. Part of that is built around the inevitability of narcissistic collapse from an emotional standpoint. The other is that the audience is told they are forgiven for the malice against the characters. Kendall, Shiv, Tom and the rest can't even look at themselves. Not what they truly are. And since they can't, it's OK for you the viewer to take joy in their fall. In their suffering. The manipulation in the writing, score, visual and tone inflection wants you to assess that the only answer is death. That the world is a better place when Logan Roy dies. And that his children are weak pathetic failed contenders for the throne of being worthy enough to be so despised.
Head writer Jesse Armstrong gave a speech at the Emmys that he shouldn't have done. HBO traditionally does not want that kind of press engagement. They want prestige television, ratings, critical acclaim, money and a certain level of cache with the general viewership.
Go watch Armstrong at the Emmys. While the baseline structure of the show is built around being derivative of Rupert Murdoch and his media empire, it's not a huge secret who the Roy family are constructed from and why. Armstrong is gaslighting the audience -
Why isn't he dead now? Why don't you want him dead? Doesn't he deserve to die? Why aren't you strong enough and pure enough to kill him?
But the biggest mistake was the caricature that is Cousin Greg. Think about the real life counterpart for Greg. The young but far too tall "relative" or "son" of a current widely despised highly public malignant narcissist that is constantly in the national daily media cycle. This is an open violation of an informal agreement made in the mid 90s by all the networks. Making Greg a failed clown and implying he's the product of even more cuckolding is too far. It's one thing to imply all the women in the Roy family, and their real life counterparts, are whores. That's vicious enough on it's own. But you aren't supposed to go after civilians. Armstrong decided he should make the audience visualize what [EDIT - Name Redacted / "Tim Tax" ] will become in absolute terms. That this is all OK because it's only a "projection" of the future. But the kid is a civilian. You aren't supposed to go after civilians.
The talk between Karolina and Hugo with Kendall about post Logan spin control is a rationalization. It's trying to normalize what Armstrong is doing. And he's doing things that he shouldn't. It opens the doorway to use mass entertainment to settle grudges against everyone else's children as a means to proxy attack someone deemed too much of a public villain.