The City Found $100 Million… While Homelessness Keeps Rising

There’s a moment in The Wizard of Oz where Dorothy and her friends realize that while the Emerald City looks powerful and magical, when they pull back the curtain they find a system built on performing power instead of results. Portland just had one of those curtain moments.

The city recently discovered roughly $100 million in unspent housing and homelessness funds, at the same time our houseless population continues to grow. We are reducing shelter bed numbers and more neighbors are living and dying on our streets. Despite a complex apparatus set up to support our most vulnerable, the problems persist and expand.

No one woke up and decided, “Let’s not help people”, that’s what makes this a Yellow Brick Bureaucrat problem.

The system followed its rules.
The forms were filled out.
The committees met.
The reporting boxes got checked.

And still; people are sleeping unhoused.

That is what happens when a system becomes more accountable to procedure and process than to purpose. When government loses its way, it usually isn’t because people stop caring, it’s because risk management replaces moral urgency. Our politics have become a game and the public just keeps losing.

Every additional approval layer exists for a reason:

• Prevent misuse

• Ensure fairness

• Protect public money

Those are good goals, but when bureaucratic layers multiply faster than outcomes, help moves slower than harm. Homelessness is a crisis where time is the most expensive currency we have. This isn’t about blaming individuals. It’s about asking harder structural questions:

• Why can we allocate money but not deploy it quickly?
• Who is responsible for results, not just compliance?
• Where are we rewarding caution instead of effectiveness?
• What would it look like to measure success by people housed rather than dollars accounted for?

I’m running because I believe government should work like the Yellow Brick Road was supposed to:

Clear.
Direct.
Guiding people toward safety and stability — not looping them through endless corridors.

Portland is full of public servants who want to solve this problem. Oregon is full of communities ready to help. But wanting is not enough; structure matters, leadership matters. Courage in governance should look like simplifying systems that have quietly grown too complicated to function.

If you’ve ever tried to navigate housing assistance — for yourself or someone you love — I want to hear your story.

Because good policy starts with listening to the people trying to walk the road.