Of all the sorry and pathetic and pitiful characters that make up the Roy menagerie, Con is definitely the saddest and the one that elicits sympathy. Con is the kind of guy, with the kind of life and emotional and psychological circumstances who you read about that ends up eating a pistol.
Another thing that struck me, for really the first time over four seasons, is how rare and brilliant a businessman Logan Roy is. I know it's supposed to be assumed, because in our culture we are trained to believe being a billionaire means you are brilliant, but I think most of us watching this show have lived long enough and seen enough to know that's not necessarily the case and true.
But on the back of his, "you aren't real figures.." speech and his rousing "You are Pirates!" speech to his ATN folks, along with all the deal and people machinations, it seems that Logan is the rare businessperson who could have made Waystar what is ended up becoming and valued which circles back to the premise and early season questions explored which we see a lot in real life: when a special person creates something and his kids are not special, businesses fail.