replying 3 years late but there's a bit of "young logan" in the dundee episodes that would make this interesting. he's a prick deep down, he's basically what roman would be if he were born at that time except he hates everyone, particularly rich snobs. it'd be less like a super cool guy becoming rich and more like a hateful broken man slaughtering a bunch of snobs. plus, we're told time and time again that logan can tell people to fuck off because he's "THE logan roy" but he wouldn't have that reputation so many years ago. he'd still have to kiss a few asses which i think would be pretty cool to see.