I think Tony was a lot more complex than simply being a monster. Phil was a monster - even Paulie and Chrissy, real freaking psychopaths - but it's a lot harder to define Tony purely as a monster. Behind the toxic masculinity, guilt, crime, and murder, there was somewhere a human being who wanted to be loved. But as you wrote, he also wanted everything.
The guy you used to drink with probably had fears that one day he would end up like Tony did. If I were him, I'd fucking hate the ending, too.
Great essay. Happy birthday, John!