On November 3, Multnomah County picks a new chair, and for the first time we’re doing it with ranked choice voting. The chair runs a roughly $4 billion government that handles the “people stuff”: homeless services, mental health and addiction care, jails, the health department, libraries, even the animal shelter. Whoever wins inherits a squeezed budget, a city-county homeless services agreement up for renegotiation, and a public that’s short on patience.

This week I sat down with one of the three candidates, Commissioner Shannon Singleton. Shannon is a trained social worker who has spent her career inside the housing and homelessness system. She worked at Cascadia Behavioral Health and the Portland Housing Bureau, ran JOIN, advised Governor Kate Brown on housing and racial justice, served as interim director of the Joint Office of Homeless Services, and in 2024 was elected to represent north and northeast Portland on the county commission.

Here’s the twist most people don’t know: her District 2 seat is on the same ballot as the chair’s race. To run for chair, she had to give up the job she has now.

In this episode:

* The childhood memory that set her on this path, and how an accounting major ended up in social work

* Marching from Philly to New York, and working with survivors in a small New Mexico town

* The woman who lived at the SAFE shelter for nearly three years, and why Shannon fought the rules to keep her there

* How a data nerd went from Housing First skeptic to believer

* Why she gave up a likely reelection to run for chair

* Her management philosophy: asking “what will it take?” instead of “why can’t we?”

* Why HR 1’s Medicaid cuts scare her, and what the county can do about it

* 720 deeply affordable apartments in the pipeline against a need of 36,000

* A positive vision for Portland: Preschool for All, the creative economy, and murals

* Flipping the budget process so it starts with outcomes and the people served

* What “progressive” means when everyone claims the label

* The endorsement that means the most to her

* Tales from the trail: doorknocks, forums, and the snack bin in her back seat

Learn more: ShannonSingleton.org, where you can also sign up to knock doors or write postcards.

Vote: Ballots go out October 14. Rank your choices and return your ballot by November 3.

Missed our episode with former County Chair Deborah Kafoury? Go back and listen. It’s the perfect primer on what this job actually is.

Thanks to our Season 3 sponsor, Corbett Hill Wellness. If your business or organization wants to support independent civic media in Portland, reach out. If you got something out of this episode, share it with a friend who’s still figuring out how to rank this race.

Schmidt Show PDX is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.

We’re less than a month from Election Day, and the headlines are worrying. The president is attacking vote-by-mail. The DOJ is threatening election officials. People are talking about ICE at drop boxes, and some Oregon ballots are likely to be rejected because the mail is too slow. So I went straight to the person running Oregon’s elections: Secretary of State Tobias Read, who at 6’7” is also the tallest guest in Schmidt Show history.

What we covered:

* The job you didn’t know he has. The Secretary of State is also Oregon’s auditor, and his office built a statewide risk map to decide where to look first.

* Playing defense against D.C. Federal election-security staff vanished days into his term. Since then Oregon has faced an executive order trying to rewrite election law, the SAVE Act, and a push to use a flawed federal database to check voters’ citizenship.

* “No, thanks.” The DOJ sued Oregon for its voter data. The judge tossed the case from the bench, and the feds are now 0-for-25 nationally.

* Why late ballots are piling up. All of Oregon’s mail now gets postmarked at one facility in Portland, which is why 7,314 primary ballots were rejected for late postmarks in this years primary.

* More drop boxes. About 20 new ones are coming, and BallotTrax text alerts are going statewide - sign up for BallotTrax when it becomes available in your jurisdiction.

* The fraud myth. Over 19 years and 60.9 million ballots examined in Oregon, ONLY 38 cases of improper voting during that entire period.

* Lightning round. What to do about ICE at drop boxes, the National Guard, hacking, a canceled election, or a refusal to certify. On that last one, Read’s answer: Oregon certifies its own results.

Key dates 📆

* Oct 13: Register or update your address

* Oct 14: Ballots mailed

* Oct 21: No ballot yet? Call your county clerk.

* Oct 27: Last day to mail safely

* Nov 3: Election Day. Ballots are due by 8 p.m.

The short version: Use a drop box. Any drop box in Oregon works. If you’re mailing, send it a week early or ask the post office for a hand postmark. Check your voter registration status at OregonVotes.gov.

Your homework: Check your registration, talk to a neighbor, and don’t let fear keep you home. VOTE!

Thanks to our sponsor, Corbett Hill Wellness. If you’d like to sponsor the show, reach out. And if you liked this one, leave a review, tell a friend, or share it. See you next week!

Schmidt Show PDX is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.