Lincoln Square

Lincoln Square

Newsletters

Winners & Losers | Voting Rights & Wrongs

A justice who's an originalist except for when "things change."

Sam Osterhout's avatar
Sam Osterhout
May 04, 2026
∙ Paid

Great stories have great characters. And great characters are built out of flesh and blood. A good hero isn’t flawless. They aren’t always good. They make mistakes, and sometimes their flaws verge on fatal. The greater the flaw, the greater the exuberance we all feel when they overcome it to succeed in the end.

A great villain wants something beyond the literal object of their villainy. Yes, they are going to destroy the city. But they also want to show their mom how great they are!

In fact, one of the great strengths of Trump is his seemingly endless well of badness. If he were a movie villain, he’d need some workshopping. It’s human nature for us to wait around for redemption, for the qualities that will make him a whole-cloth member of the human race to spring forth. We tend to give people — even villains — the benefit of the doubt. Or, at least, we wonder what trauma in their lives led to their villainy.

Winners & Losers is a special feature for our Lincoln Loyal paid subscribers. Upgrade your subscription today.

But Trump is irredeemable, fully. He steals money from everyone. Literally everyone. He would sell his own children if it benefited him. He sells the men and women who devote their love to him shitty swag — watches and coins and NFTs and pennants and wallets and piles upon piles of overpriced giftshop slop. They believe buying his garbage makes him love them. And he lets them believe that. He’s destroying the country because, well, that’s all he’s got.

And, of course, there are those allegations that he abused children.

His actions are unforgivable. His villainhood is so cartoonish as to be shockingly one-dimensional, and that’s why it works. I still want him to reveal something that feels authentically good. Or, maybe even just authentically okay. Or at least find some deep well of trauma that led him to this awful conclusion to explain why he’s doing this to us. But nothing like that is coming.

Watching the world shatter around us is like sinking into an endless Netflix binge of the dumbest, most engrossing, high-stakes, good-vs.-evil series of all time. Partly because for so much of it, most of us have the awful feeling of being bystanders. While the actions of the administration and its proxies have enormous impacts on our day-to-day lives, sometimes it feels like all we can do is sit back and watch it happen, like we’re watching it on TV.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2026 Resolute Square PBC d/b/a Lincoln Square · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture