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Winner of the Year | Round 2: It's All about the Culture

These nominees may not always change laws, but they do change people's minds.

Sam Osterhout's avatar
Sam Osterhout
Dec 22, 2025
∙ Paid

The year we all thought would be terrible is coming to a close, and … it was probably more terrible than we imagined.

But as Joe Trippi said on the latest episode of Two Joes (we’ll release the podcast later this week, fyi), we’re ending the year in a better place than maybe we imagined. There have been some jaw dropping electoral wins by Democrats. Republicans in +8 seats see very clearly that they’re either going to have to do big numbers in fundraising … or retire.

And many of them are choosing the latter option.

Trump’s polling is finally catching up with the reality of his terrible policies/personality. People are catching on that Trump is, well, Trump. And they hate it.

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These are all good things that I wish never had to happen. As the new signage goes up on the Kennedy Center (that I had to type those words gives me side cramps), it’s important to understand that next year is going to be tough. All things could — and probably will — get worse before they get better.

But we are Americans, and there are signs of hope.

Enter the Winners.

Two weeks ago we crowned RFK Jr. as the King Loser of the Year in a landslide victory. Last week we began the Tournament of Winners, round 1, which featured electeds who are doing the work: Arizona U.S. Senator Mark Kelly, Illinois Governor J.B. Pritzker, and California Governor Gavin Newsom.


Newsletters

Winner of the Year | Round 1: The Leaders

Sam Osterhout
·
Dec 15
Winner of the Year | Round 1: The Leaders

Last week, we crowned the Loser of the Year. RFK Jr. took it by around 20 points. It wasn’t even close. That’s not totally surprising, as he seems set to remove protections against infectious diseases that we’ve taken for granted for decades.

Read full story

This round features Winners from culture. These are the people whose actions might not change policy, but they change hearts and minds. They aren’t suing the administration in a court of law, but they are taking the regime to the cleaners in the court of public opinion.

That’s not to say that their actions don’t matter. They do. Absolutely. But how they are handling the current situation works as an example for the rest of us, who don’t have the same access to power as, say, Gavin Newsom.

Before we get started, a few notes:

  1. There are a million people who could have taken any one of these candidate’s place. I encourage you to write in someone I’m missing.

  2. You have to be a paid subscriber to add your vote to the comments. But you don’t have to be a paid subscriber to share out!

  3. I’d love to hear why you made your choice. I will feature some of your comments in next week’s Winner Reveal.

Without further ado…

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