Trump says Portland needs “cleaning up.” What if Portland is actually a model of democracy in action—messy, loud, and making progress?

If Donald Trump and his MAGA minions don’t want to be called fascists, here’s a thought: stop acting like them. Instead of threatening West Coast cities with troops, raids, and funding cuts, a real leader might look at how places like Portland are tackling their own problems—head-on, locally, and democratically. A great leader might even ask, “How can I help?”

In this episode, Greg talks with Kari Chisholm, a veteran Oregon political strategist, about what Portland actually looks like beyond Trump’s caricatures. From cleaning up its streets with compassion to making the government more representative, Portland is moving forward—loudly, imperfectly, and authentically.

Together, Greg and Kari take on the myth of Portland as a “failed city,” expose the cynical national attacks meant to delegitimize urban progress, and ask: what if the West Coast leaned into its independent streak and set its own democratic example for the nation?

In this episode, we cover:

• Why Portland’s reputation as a protest city is misunderstood—and why protest is part of democracy
• How local leaders are tackling homelessness and ICE abuses despite federal hostility
• What MAGA attacks on “blue cities” reveal about authoritarian impulses in Washington, D.C.
• Why speed and clarity matter when the Trump administration is “moving fast and breaking things”
• What Portland’s choices say about the broader West Coast’s capacity for autonomy

About Our Guest:
Kari Chisholm is an Oregon-based political consultant and strategist. As the founder of Mandate Media, he has worked on campaigns across the Pacific Northwest and nationally for more than two decades. He is also the publisher of BlueOregon and a sharp observer of how West Coast politics both clash with and influence national trends.

Resources & References:

• Swift Public Affairs - Kari’s consulting shop
• Portland Transition: Geographic Districts
• “Portland Says ICE Violated Agreement with City 25 Times by Holding Detainees Too Long,”
• Portland Blueprint to End Unsheltered Homelessness
• “Oregon Law Rolling Back Drug Decriminalization”
  
  

Related Episodes:

• 29 How to Build a Firewall Against Hate? With Heidi Beirich
• 14 Could Ambitious Civic Projects Jolt Us Back to Trusting Government? With Nolan Lienhart
• 10 What If Blue Cities Got It Together? With Sandeep Kaushik

Join the conversation: Walking your dog through Portland to the food trucks or brewery, you catch a glimpse of Mt. Hood, would you say Portland – or other colorful parts of the West Coast – is in need of clean-up or full of character? What if we embraced our role as a providing ground for democracy with updating the ways we govern our own cities, counties, and towns? 

Share your take wherever you follow or send me your thoughts, questions, comments and constructive suggestions to [email protected].

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Thank you to:

• Guest: Kari Chisholm (and to Sandeep Kaushik for the intro)
• Producers: Tim Wohlberg, Valerie McTavish
• Family & friends who have hosted me many times in Portland (yes, even Timbers fans)