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.

Election Day is less than seven weeks away, and one of the most consequential races on your ballot is for a job most Portlanders couldn’t describe: Multnomah County Chair. The incumbent isn’t running again, so no matter who wins, the county is getting a new leader and a new direction.

To help make sense of it, I sat down with someone who knows the job better than just about anyone. Deborah Kafoury spent 14 years on the Multnomah County Board of Commissioners, eight of them as chair. She guided the county through the COVID-19 pandemic, heat domes, wildfires, and more than 200 nights of protest. Before that, she served in the Oregon House, including as Democratic leader. She’s now chief of staff at Portland Public Schools.

Deborah and I worked side by side through some of the hardest stretches in this community’s recent history. We had a candid, funny, and useful conversation about what the chair actually does and what voters should be asking the people who want the job.

In this episode:

* What the county chair actually does. Deborah’s shorthand for the difference between the two governments: the city builds physical infrastructure, and the county builds human infrastructure. She also explains why the chair acts as both a governor and a legislator.

* Why management experience matters. Every county employee, all 7,000 of them, ultimately works for the chair. Deborah explains why voters should ask whether candidates have run a team before, and whether they did it well.

* Her father’s rule for surviving public life: hire people smarter than you.

* What’s waiting on the next chair’s desk: homelessness, affordability, and projected budget cuts. She also explains why she sees the budget as a moral document.

* Working across the aisle. She tells how Republican partners made the Sellwood Bridge and the new county courthouse possible, and why the Republican House speaker threw her a baby shower.

* The questions to ask at a house party. Deborah’s advice: ask about trade-offs, and ask candidates who they’ll spend their time listening to.

* The red flags to watch for. Be wary of promises to end homelessness on a deadline, guilt-by-association attacks, and the idea that asking hard questions counts as getting things done.

* Her new role at Portland Public Schools, and some good news: test scores are up.

Plus, In the News: Our trash news correspondent Elinor Jones turns her attention to a group that doesn’t get nearly enough attention: men. She covers robots that can’t walk downstairs, Mitch McConnell’s return to the Senate, and Pete Hegseth’s testosterone plan for the military. Find more from Elinor in the Portland Mercury’s Trash Report.

Your homework: Attend a house party, knock some doors, talk to your neighbors, make sure you’re registered, and get your ballot in.

Season 3 of SchmidtShow PDX runs through Election Day. If you like what we’re doing, subscribe, share this episode with a friend, and leave us a review.

This episode is brought to you by Corbett Hill Wellness Center, offering chiropractic, massage, acupuncture, naturopathic medicine, and more. Interested in sponsoring the show? Reach out. We’d love to have you.

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

It’s back to school season, which means it’s also back to the annual drama over Portland Public Schools — superintendent contracts, building closures, classroom consolidations. But this week, Mike zooms out to the bigger issue hiding underneath all of it: Oregon currently ranks 50th in the nation in fourth-grade reading proficiency.

To talk about it, Mike welcomes a guest who’s impossible to ignore — quite literally dressed as a two-foot pencil. J. Schuberth is the creator behind “Pencil for Governor,” a write-in campaign designed to force Oregon’s literacy crisis into the spotlight. Jay walks through how a joke among friends turned into a real campaign, what it’s actually like knocking on doors in a pencil costume, and why it took a mascot to get people talking about something this serious

Together, they dig into what states like Mississippi, Louisiana, and Tennessee did differently to turn their reading rankings around — and lay out a five-step pledge for what Oregon could actually do about it. It’s part satire, part policy deep-dive, and a reminder that sometimes it takes something absurd to make people pay attention to something urgent.

Plus: Elinor Jones returns for a back-to-school edition of “In the News,” covering celebrity balloon arches, Meghan Markle’s UK school controversy, and JD Vance’s stay-at-home parent stipend proposal.

In this episode:

* Oregon’s 50th-in-the-nation ranking in 4th grade reading proficiency

* The origin story behind the “Pencil for Governor” campaign

* What Mississippi, Louisiana, and Tennessee did to improve reading outcomes

* The five-step pledge for fixing literacy in Oregon

* Pencil’s picks for governor-for-a-day: policy, press conferences, and photo ops

* In the News: back-to-school culture wars, royal school drama, and the politics of parenting

Thanks to our sponsor, Corbett Hill Wellness, for supporting this episode. If you or your business would like to sponsor SchmidtShow PDX, reach out — your support keeps this project going.

Links:

* You can read Elinor Jones at the Mercury Trash Report

* You can learn more about Pencil’s run for Governor

* Sign the Petition to build support for fixing Oregon’s reading outcomes!

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

U.S. Senator Jeff Merkley joins Mike for a wide-ranging conversation on the state of the Senate, institutional trust, and what comes next — plus the debut of a new segment, “In the News,” with first-ever Schmidt Show correspondent Elinor Jones!

In the News with Elinor JonesA look back at three cultural giants lost this week — Dolly Parton, Tim Curry, and Peter Cullen (the voice of Optimus Prime) — including the surprisingly dark origin story of Dollywood, a brief history of celebrity theme parks, and a case for reviving the Rocky Horror midnight-screening tradition as an afternoon one.

Senator Jeff Merkley

* His old nickname, “Smash,” and how he unwinds back home in Oregon

* Favorite hidden-gem spots in Oregon, including the Oregon Treasure Quest

* The Senate then and now: from a 30% approval rating in 2009 to a historic 10% low today

* Ringing the alarm bells to recognize and fight the rise of fascism

* Growing inequality, being locked out of power across all three branches, and the case for “fighting fire with fire”

* The real mechanics of restoring trust: insider stock trading on Capitol Hill, Supreme Court ethics, and the influence of Citizens United

* ICE and the record-setting 50,000+ arrests in July

* Advice for the next generation of leaders following in the footsteps of Edith Green, Mark Hatfield, and Jeff Merkley himself

Lightning RoundFavorite Dolly Parton song, whether there’s a blue wave coming in November, election security, Mitch McConnell’s status, gardening, Reagan-era tax rates, and more — straight from listener-submitted questions.

Links mentioned

* Ring the Alarm Bells: The Ten Rules of Trump’s Authoritarian Playbook

* Oregon Treasure Quest

* Crystal Crane Hot Springs (Burns, OR)

* Carnivorous bog boardwalk (Florence, OR)

* Elinor Jones’ “Trash Report” at the Portland Mercury

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

Mike sits down with sitting Oregon Supreme Court Justice Bronson James — public defender and private practice lawyer turned Circuit Court, Court of Appeals, and now the state’s highest bench — for a rare, wide-ranging conversation with a sitting Justice. They start with comic-book tattoos and an actual ongoing Oregon Supreme Court Dungeons & Dragons campaign, then dig into the real stuff: what privacy even means in a world of data brokers and license plate readers, why Oregon’s 1859 constitution offers stronger protections than the federal floor, the “laboratories of democracy” under strain from federal preemption, and the perfect questions to ask judicial candidates this fall in your backyard gatherings. They close on judicial courage, Brown v. Board, and what it actually looks like when a judge is doing the job to improve the lives of the people they serve.

Topics Covered

* Comic-book tattoos and an actual ongoing Oregon Supreme Court Dungeons & Dragons campaign

* His path to the bench: Reed College, the dot-com boom, PhD guilt, and why he ended up in law school “not for any particular reason”

* What surprised him at each level of the job — trial court, Court of Appeals, and now the Supreme Court

* A plain-language tour of Oregon’s court system for non-lawyers

* What privacy actually means today, and why the law struggles to keep pace with technology

* Oregon’s constitution vs. the federal constitution — how Article I, Section 9 differs from the Fourth Amendment, and Hans Linde’s legacy building Oregon’s independent constitutional tradition

* Contested judicial elections in Multnomah County this November, and the real mechanics of how judicial campaigns work

* The information gap between lawyers (who can read a judicial candidate’s philosophy easily) and voters (who mostly can’t)

* Why “just calling balls and strikes” is a myth, and what actually reveals a judge’s character

* Judicial courage, Brown v. Board of Education, and MLK’s Letter from Birmingham Jail

* Closing advice: why headlines rarely tell the full story, and how listeners can become better-informed voters on judicial races

About Our Guest

Justice Bronson James sits on the Oregon Supreme Court, appointed by Governor Kate Brown in 2022 and elected to the seat in his own right in 2024. He previously served on the Multnomah County Circuit Court and the Oregon Court of Appeals, and worked as a public defender and in private practice before that. He teaches Oregon constitutional law at Lewis & Clark Law School.

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