What Happened When I Sat Down With My "Enemy"

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Wilk Wilkinson at Braver Angels

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May 10, 2026, 9:08:40 AMMay 10
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Dear Newsletter,

A few weeks ago, I sat across from Minnesota State Representative Walter Hudson for a recorded conversation through The Enemies Project, a program built on a simple but radical premise: that the people we've written off as adversaries might have more in common with us than the story we've been telling ourselves.

Walter is a once "never Trump" Republican who has moved firmly into the MAGA camp. I voted for Trump three times. I'm not in that camp anymore. So on paper, we should have had plenty of ammunition for each other.

We started talking about immigration, specifically the fractures that aggressive ICE enforcement has created, not just in Minnesota where we live, or even across the country, but inside the Republican Party itself. That's where things got interesting fast. What began as a policy disagreement revealed something deeper: we see the "greatest civilizational threat" facing America very differently. That's not a small gap. That's a fundamental one.

And yet.

By the end of the conversation, Walter and I had found something neither of us expected to walk away with: a real bond. Not agreement. Not a debate win for "either side". A bond. The kind that comes from actually listening to someone's story instead of their talking points.

That's the power of The Enemies Project, created by renowned mediator and bridge-builder Larry Rosen and his daughter Sadie. The format isn't magic. It's just structure that slows you down long enough to hear the human behind the position. Larry and Sadie create the conditions for something rare: a conversation where both people leave a little more whole than when they started.

Here's what I keep coming back to: there is always a deeper story. Walter's story. My story. Yours. Most of us are carrying experiences, fears, and convictions that make perfect sense from the inside but look like pure obstinacy from the outside. When you never get past the surface, you never find out why someone actually believes what they believe. You just confirm what you already thought about them.

That's the trap. And Braver Angels exists to help us out of it.

The conversation wasn't comfortable. It wasn't supposed to be. But discomfort, in the right container, with the right intent, is where real understanding begins. Walter and I disagree on some significant things. We probably still do. But I respect him. And I believe he respects me. That didn't happen in spite of our differences. It happened because we were willing to sit with them instead of running from them.

You can watch the full episode here: The Enemies Project — Wilk & Walter


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If it moves you, share it. Not to score points, but because someone in your life might need to see that this kind of conversation is still possible.

Larry and Sadie Rosen will be at the Braver Angels National Convention in Philadelphia this June. You won't walk out of their session having experienced the full depth of what they do — that takes time, vulnerability, and the right person sitting across from you. But you'll get enough of a taste to understand the why behind it, and that curiosity might just be the thing that changes how you show up in your next hard conversation.

We won't agree our way to a better country. But we might just listen our way there.

— Wilk

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***

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