@pynkhues wonderful response to my ask has sent me on a tangent again.

There's something about Logan talking Willa through his medal collection I've always found fascinating and a little disturbing. It makes me wonder if like Roman with Tabitha and presumably Grace, part of why Connor was first drawn to Willa is because he thinks she's someone Logan would find attractive (blech). Maybe one thing Connor has in common with his old man is a shared juvenile taste in pretty ladies who are nice to them and appear to agree with them about everything.

Look at S1 Marcia always having Logan’s back no matter what shitty thing he does to the kids. Look at Rhea playing the role of helper and the acquiescing companion. Look at Kerry becoming his favorite when she echoes all his opinions. Then look at how sweet and defferential Willa is when she asks him about the medals, and how almost strangely gentle he is with her in return. That’s Logan Roy’s type: women who treat him like a Very Special Boy that must be Respected and Pampered. He would never admit it, and I’m sure he likes some surface feistiness like Rhea displays when they first meet, but at his core Logan is just as emotionally stunted as his children, moreso. Ultimately he wants someone to take care of him and soothe his ego. Caroline’s inability to do that probably played a not insubstantial part in their divorce.

So If Sally-Anne was the interviewer we see in Argestes, I wonder if Logan became infatuated with her when she flattered and cajoled him into a 60 Minutes-style interview -- only for him to watch the broadcast and discover he comes off as the demented little troll he is, with no softening or defending on Sally-Anne’s part. Hence the "black cloud after Sally-Anne" and his deep paranoia about a biographer "sniffing around his panties".

…However, if that were the case, I think Roman and co. would associate that with her instead of horses and harps. It's probably another woman coincidentally called Sally-Anne. Still, fascinating to think about.

Also, re: Willa: I recently re-watched Austerlitz with subtitles on. I never caught before that, after she tells Kendall to fuck off for his high-class call girl line, she quickly says, “That’s okay, I have an aunt who’s an addict. It was wonderful getting to know you all.” Willa is definitely using the Roys to her advantage when it comes to funding her plays, but I do think this scene is telling: she’s probably the nicest person in the show. Maybe not a great person, but the best among them. And it’s important to remember that even though she’s genuinely fond of Connor (I think she loves him, she’s just not in love with him), she has seen what this family is capable of. Can she really trust how this “nice man” Connor would react if she tried to leave him?

Ugh, I do hope she writes that hit tell-all play about the Roys and uses the profits to get the hell away from them all. Run, Willa, run!!