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The Last Winners & Losers ... For Now

Tired of losing? So are we. So we're focused on what's next.

Sam Osterhout's avatar
Sam Osterhout
Jul 27, 2026
∙ Paid

Sometimes Winners lose, and Losers win. That was the premise that led me to write this column each week. It might merely sound like a clever turn of phrase, but our entire timeline is based on that premise.

All the chaos. All the catastrophe. All the pain and suffering. The potential collapse of our empire, really, is baked into that very simple construction.

Look at it another way. Replace Winners with Heroes, and Losers with Villains, and you have the basic building block of virtually every movie ever made. The Hero is flawed. Always. It’s their flaw that is in tension with their unique ability to overcome the obstacle in front of them. The broad objective isn’t necessarily to vanquish the Villain. In fact, the Villain is simply a force standing in the way of the Hero’s ultimate objective.

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You have to defeat the dragon to save the princess.

Defeating Trump cannot be our ultimate objective. But to achieve our ultimate objective, we must defeat Trump.

Our ultimate objectives are complex, of course, but they include words like freedom and equity, peace and justice. How these vague, shiny words apply to our daily lives, well, we should be able to decide. Maybe that itself is the ultimate objective — the ability to determine the path of our own lives.

The Losers I write about in this column are sometimes grifters, sometimes they’re frauds. They are fools and cowards and fascists and white Christian nationalists. Whatever they are, whatever their personal objective, they are standing in the way of where we need to go.

This will be the last Winners & Losers. Maybe forever. Maybe for a while. I love writing this column, but, honestly, I want to write less about the Villains blocking our path forward, and more about where that incredible path might lead.


Newsletters

The High Court, of Course | Winners & Losers

Sam Osterhout
·
Jul 20
The High Court, of Course | Winners & Losers

You have chosen a winning Loser! And it wasn’t even close. I’ll reveal your choice in a second. But first, let’s set the table.

Read full story

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