It's Logan's fundamental flaw of flattening out the emotional dexterity of people and rendering them into economic units that elevates Succession into a tragedy. More so, it's the eventual spilling of business and politics into the personal that reverberates through all the character dynamics in the show, making it a prestige drama.
In television, a familiar set of tropes tend to follow around a main character’s death, often accompanied with grand overtures and keyed up hoopla. How else do you reinforce the inevitability of something such as death? With the third episode of season four, called 'Connor's Wedding', the show creates suspense and shock out of the very thing that was staring right in front of our eyes both in the show's literal title and the events from its first ever episode.
The possibility of one or another sibling pushing their father to a physical breaking point has always been a recurring theme that drove the suspense in the show. Alas, they had now done it, together. While Roman sits down on the deck-floor while thinking about the last mean words he had said to his father (his last words to Logan included, “Are you a cunt?”) and whether that would have triggered something, the other two - equally flustered - cope with the guilt manifested by denial in their own ways.
"You're not serious people", Logan says to his kids in the second episode of the season after putting his guard down, while trying to convince them of the GoJo deal. Now with them literally ashore with their anchor gone, will their father's ruthless absence prove to be his greatest power move? The denial of each Roy sibling has a hard-hitting subtext to it, as they had devoted their entire lives around trying to impress and live up to the (undefined) expectations of their megalomaniac father.
It's not that Connor doesn't have insecurities of his own, but it was his acceptance of his father's true self ever since the start of the show that always made sure he didn't chase his life behind impressing him by throwing empty hijinks, pretending to be someone he's not. In the sad karaoke monologue from the second episode, Connor also said, “The good thing about having a family that doesn’t love you is that you learn to live without it".