i know fantasies are fantasies but it's kind of funny to me that the image of recasting yourself as like this silver-tongued amoral pragmatist grifter has remained so attractive despite exposure to the likes of martin shkreli and crypto weasels and all the other versions of what that looks like in real life, which is as something not just "morally wrong" but also like, viscerally unappealing and unglamorous.. and it survives as fantasy in part bc it's so fitted for the world those guys helped to make, but also because it kind of repudiates them by presenting that condition as something rogueish and exceptional instead of the bleakly universal state of affairs it is. it's like there's something uncanny about how charmless that stuff is in practice and so fantasy has to work harder than ever to fill the gap.
I think part of this also is that in the fantasy it's never truly as amoral as it's made out to be. The grifter rogue always has a heart of gold as much as they try to deny it, and the people they grift are always somehow detestable—those with money or power, those who are grifters themselves, those who who are cruel or even just hubristic. This is a mandate of the narrative. Real grifters make their ducats not by big cons of big targets, but at scale: they drain a little bit of money from a lot of poor and desperate people, amortizing their exploitation across thousands and thousands of tiny sins.
