#this came about actually because i'm writing post-canon and it's important to me to detangle his logic

[aquickstart]

one thing that's been talked about here and by creators and is obvious but still important to articulate (to me) is that oliver is not envious of the cattons because they are wealthier than him, necessarily. it's not about the money. or it is, but in a way that everything in life is about money: no matter how much you have, you kind of always want more, because want is a very strong driver. he's not coming from a place of poverty or any financial need at all, and he is not genuinely burning with the anger at the rich as a working-class guy constantly overpowered by them. there is no righteousness of the oppressed in his motives; sure, he "knows how to work", but to me—and this is, again, personal interpretation—the more important part is that the cattons "made it so easy" for him to take everything from them. it doesn't matter where oliver is coming from, ultimately (which is why he is so pointedly an upper middle class kid, quite comfortable, not a struggling genius he paints himself to be). for oliver, and for his audience, what matters is what he wants, not why he wants it; how badly he wants, how deep inside his own desire he is.

in short, it's not that the cattons had something he didn't have. it's just that they had something he wanted.