Lincoln Square

Lincoln Square

Share this post

Lincoln Square
Lincoln Square
Winners & Losers | The Greatest Loser of All Time
Newsletters

Winners & Losers | The Greatest Loser of All Time

All the world's a stage for Trump.

Sam Osterhout's avatar
Sam Osterhout
Aug 18, 2025
∙ Paid
85

Share this post

Lincoln Square
Lincoln Square
Winners & Losers | The Greatest Loser of All Time
11
9
Share

Welcome to your weekly scorecard, where I take a tiny pencil and count up all the pins dropped to reveal the week’s biggest Loser and most impressive Winner.

You’re reading this on Monday, but I file these columns on Friday. As I write, I’m waiting for news out of Alaska, where Trump is preparing to nestle himself inside Putin’s body like a tiny Matryoshka doll. In the stories we tell our grandchildren about this era, this “summit” will likely be the story of this week (watch Stuart Stevens’ Friday video about it at the end. It’s devastating). But this week contained multitudes. It’s been exhausting, to be honest.

Remember how the week started? Trump held a press conference to announce that he was activating the National Guard to take over Washington, D.C. As Putin arrived in Alaska, we are starting to see the terrifying videos of armed men in masks pushing their way through a city in which they do not belong.

Grandkids: So he sent troops into D.C. and welcomed Putin to America in the SAME WEEK?

I will tell you up front that my loser this week is Trump. But it’s not for any of the above reasons (or, not exactly). I’ve shied away from picking him for this column in the past because … duh. He’s the biggest Loser on Earth. A nepobaby who failed upward his entire life until his failures became so big they lit the world on fire.

Share

I’m always more interested in the Losers who actually look up to this guy. Can you imagine? Go find the world’s cheesiest, creepiest fraud and do whatever it takes to make him love you. How there are still Losers like this to write about, I don’t know. But they are in seemingly endless supply.

Every week is a heartbreak, I know. Every week we reach a new low. But with the flood of bad news, sometimes we miss the forest for the trees. Something new happened this week that is so absurd, and yet so emblematic of the entire mess we find ourselves in that I think we need to hold on it for just a little bit. We need to linger in the absurdity to understand exactly what we’re looking at, what’s actually happening.

On a positive note, it turns out that our Winner this week seems to understand all of it. He’s not without his flaws, but he’s fighting back in a way that is appropriate to the moment.

Read on to find out why this week, of all weeks, Trump has finally made the Losers’ list, and who made the Winners’ column.

This post is for paid subscribers

Already a paid subscriber? Sign in
© 2025 Resolute Square PBC d/b/a Lincoln Square
Privacy ∙ Terms ∙ Collection notice
Start writingGet the app
Substack is the home for great culture

Share