I think he liked her enough that if she’d stayed a political consultant or had been content to boost his career in the firm more than his own, he would have made a workable marriage from it.
For someone who was offended by the thought of a hall pass on his stag do/an open marriage, he swallowed his load quick enough.
But he did know he would be able to manipulate Shiv by making her think he was hurt by it. That he could withdraw a bit of attention and feel powerful at how much she really depended on him. He knows she is more enmeshed with him than she lets on, that she uses a lot of bluster to hide a hurt little Daddy’s girl inside.
He knows she needs to feel in control and like she doesn’t need him. She’s not just a Daddy’s girl but her father’s daughter. She likes it when she kicks the puppy and he comes back.
He’s been talking about “what do we like for me?” and the business plan from the start.
But a betrayal was always on the cards if Shiv set her own eyes on the prize rather than supported him. How and when he would betray her was shaped in circumstance but rooted in his character and intentions.
He only put up with the level of shit he did because he was playing the long game. The real Tom is the person who said to Kendall he’d never seen Logan get fucked. We also see flashes of him with Greg.
I also think Logan sees himself in the slab of gravlax in a way he doesn’t in his own children. The ability to be a killer, the ability to live for nothing but the business win. It’s like being a warrior or a fighter.
I think that if one or all of his children was genuinely able to deliver a killer blow to him, to really outmanoeuvre him he’d be incredibly proud, and think they were worthy, finally have some respect for them.
But the proof of the pudding is in the eating, they have to do it, not just be judged able to do it. I think Kendall has known that for a while and it’s why he keeps going for the jugular. Because somehow he knows it it his best shot at making Daddy love/respect him. But he’s doing it for the love, not for the thrill of the kill, and so he doesn’t succeed.
But as it is, Logan is kind of embarrassed by their inability to be as sharp, instinctive and ruthless as he is.