May 2025 Endorsements: Schools

Your tax dollars. Your children. Our future.

The backside of Jefferson High School, 2021. Gaze upon its glory.

Preamble

If you haven’t voted yet please use a drop box. Voting deadline is Tuesday, May 20 and it’s too late to mail.

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Off-cycle election season is back! No extended digressions¹, let’s get down to business.

This May’s election is simple:

• Schools,

• Schools,

• Schools,
  and, of course,

• Urban Flood Safety and Water Quality

Let’s take them in reverse order.

Urban Flood Safety and Water Quality District

UFSWQD, for short.

What is it?

It’s a special district to address flooding issues and water quality isssues in Portland, obviously. It’s basically all in the name. Here’s their history. It’s existed in its current form since 2016 but various versions have existed since 1917 (which I don’t think helped folks much in the 1948 flood of Vanport).

Why is it on the ballot?

Because we pay for it, so we vote on it? Like the Multnomah County Soil and Water Conservation Districts, this is another case of Too Much Democracy.

Were it up to me, this would be managed entirely in-house by either Multnomah County or the State of Oregon. We’d hire some expert technocrats and call it a day.

But it’s not up to me, and so voters have to vote on something they don’t understand or care about, even if their lives depend on it (which, in this case, may actually be true if you live in low lying parts of North or Northeast Portland).

How am I voting?

Lori Stegmann (again) for Position 1. I’m not quite sure why she is up again after we had to vote for her in November. I also wouldn’t vote for her for other positions in the city or county, as I’m skeptical of the company she keeps. But her opponent, Leo Morley does not appear to be a serious candidate.

All other candidates are unopposed.

Multnomah Education Service District

What is it?

To quote the Mercury:

Multnomah Education Service District is responsible for coordinating education services and resources for regional school districts. MESD is one of nearly 20 ESDs in Oregon and provides everything from special education, to health services, alternative education, outdoor school, career pathways, and more.

Why is it on the ballot?

Again, I’m skeptical we should be voting on a position that we, as voters are unequipped to accurately assess the success or failure of the board. But here we are. It’s on the ballot because that’s how Oregon rolls.

How am I voting?

Susie Jones. Erica Fuller didn’t submit to the voters guide. Rebecca Yeaman seems passionate about book bans but otherwise doesn’t appear to have any relevant experience. Kevin Michael Butler is actually endorsed by a sitting member of the board, which got my attention, but the rest of his Voter’s Guide submission was generic and unhelpful—one step up from word salad. That leaves Susie Jones, who has experience in the job and was a previous educator.

Will that make her a good board member? Honestly — no idea. But “can walk and chew gum” is the bar and a retired teacher/retired community college faculty member who previously sat on the board can probably do both.

Portland School District

What is it?

It’s the school board for Portland Public Schools (PPS). I don’t know why they don’t call it the school board because it’s the school board.

Why is it on the ballot?

Because 50-60% of our property taxes go to schools, 40% of our state income taxes go to schools, and, if you’re one of the lucky few, another 3% of another chunk of your income goes to (pre-)schools.

Also maybe you have a kid or three in school.

How am I voting?

Before I get to my actual choices, I need to throw my cards on the table. Thanks mostly to late night, beer-soaked policy conversations with Conor P. Williams of the Century Foundation, I am an Obama-era school reform liberal when it comes to schools.

Broad strokes, that means I believe a bunch of things which were popular in 2009-2016 but many of which have since fallen out of fashion:

• Students outcomes first — Teachers and parents are great and their input is crucial. But ultimately the outcomes of students are far more important than any other stakeholder in the system.²

• Data-driven accountability — Yes, over-testing and teaching to the test are bad, but we need to actually measure how students are doing to understand how to best support them.

• School choice — I’m pretty skeptical of a lot of charter school initiatives (especially in red states) but I’m not a priori opposed to them. Indeed, I think school choice, when properly implemented, can be a net benefit to students from all backgrounds.

• Pre-schools, early interventions, dual-language programs, etc. all can improve outcomes when implemented wisely and funded appropriately.

• Phonics is good, yo.

Basically, it’s a technocratic and accountability-based approach to schooling grounded in data, rather than one based on… anything that isn’t that. Vibes, I suppose.³

I had hoped to vote with this lens, basing my votes on whomever most closely hewed to educational philosophy here. In practice…it was much less obvious. Mostly folks are fighting about per-student funding (which they don’t control, the state does) and the capital funding, a.k.a the bond (which they also don’t control but at least is more relevant to the gig).

There also seems to be a divide on accountability — on what we should be holding teachers and schools accountable for vs. the state. The background noise to all of this is the 2023 teacher’s strike, which was brutal for students, parents, and teachers alike.

That strike is interesting. It’s been a minute, so my memory is a bit foggy but in the binary choice of “who was right, the teachers or the administration”, I sided with the teachers. I wanted to see them get paid more, which they did. But there’s a lot of complexity under the term “administration”. It’s the principals, it’s the central office, it’s the state budget, it’s the school board.

Disentangling that is complex and I don’t pretend to be an expert. Broad strokes, I’d like to see: 1. more funding in a more reliable funding model from the state and 2. more accountability for student achievement at the district, the per-school, and the per-teacher level.

Which is to say, I want to invest in teachers and in schools but I also want to ensure accountability up and down that chain.

District 1, Zone 1:

Ken Cavagnolo has a bunch of interesting ideas on his website and is a bit of a fire-breather, in a way that resonates with me. But I’m left with a feeling of “why the school board?”

Christy Splitt seems generally well-meaning and has a bunch of rather unpleasant experiences in her time with a kid at PPS. She’s on the board now, but her term has been extremely brief so she doesn’t have much to show for it. Her platform is shallow and generic.

She wants more money for the schools, of course. Me too! I’m supportive, in principle that but it’s clear that isn’t the only answer to what ails us. Oregon is about average among states for funding-per-student but significantly below average in terms of reading and math scores.

I’ll admit this is all vibes but between her WW interview and her platform, I’m left with the feeling that she won’t force the hard decisions and trade-offs that may be required to improve outcomes.

In the end: I’m open to both and could be swayed It’s an abbreviated term, so it’s less of a commitment either way.

Realistically Christy Splitt is going to win. I’m interested to see what she does with the remainder of her term. But I’m voting Ken Cavagnolo—his background for a candidate is unusual but I’m willing to take the chance.

District 1, Zone 4:

Herman Greene has served on the board for a term. His approach seems to be students-first. I’m glad he highlighted some of the major issues with the Bond and I appreciate his realism in negotiations with teachers as well. But I don’t love his style, nor do I love that he shows up unprepared to meetings

Rashelle Chase-Miller has a strong literacy background and does appear to be prepared, for meetings or otherwise. But like with Splitt, her WW interview answers have me worried she’s going to use school funding (or lack thereof) as an excuse for the school achievement issues.

Both candidates are flawed. I won’t begrudge you for voting for Rashelle Chase-Miller. But I’m going Herman Greene.

District 1, Zone 5:

Whereas Zones 1 and 4 are “less of two evils”, Zone 5 is actually a choice between two seemingly good choices.

I love an 18 year old who is capable, knowledgable and deeply, hopelessly involved. I dig that so much. And I appreciate his lived experience, very recently, as a student; it makes me confident that he’ll focus on students first rather than other actors in the system.

I also appreciate folks who can actually make things happen in the district. I don’t care much about lights on a sports field but lead abatement is exactly the sort of infrastructure improvements we should prioritize.

I wish they were running in different districts. Since I can only vote for one, I’m swayed by Virginia LaForte’s “top 3” priorities for the district: chronic absenteeism, repairing crumbling infrastructure, and raising low reading proficiency rates.

District 1, Zone 6:

A former cowoker of Rob Galanakis described him to me like this:

Smart dude, very much the kind of technocrat you’d want making decisions. Also likely incapable of getting elected or working within a system to get shit done.

So I’m obviously predisposed to like him.⁴

But liking him doesn’t mean I’ll vote for him. Two reasons:

1. He will have to work within a system to get things done. Governing requires coalition building, which requires tact.

2. His opponent has is a strong, pragmatic candidate with the right focus for schools. Her top 3: chronic absenteeism; fairer access to the arts, apprenticeships work, and college prep courses; and taking greater fiscal responsibility. I can get behind that.

I’m voting Stephanie Engelsman.

School District Measure 26-259

What is it?

It’s a bond! A $1.83B dollar bond. It will replace an existing PPS bond, so property taxes should roughly stay flat and the money will get spent…somehow. The original plan has the majority set aside to replace three high schools, with the remainder to go towards a handful of other changes

OPB has the best rundown I’ve seen on it.

Why is it on the ballot?

Crumbling infrastructure! We have it! PPS typically pays for capital improvements via property tax funded bonds. Many districts country-wide do this, so there’s nothing unusual here. What is a little unusual is the price tag which is 50% larger than the previous largest bond in history. Inflation, man. It’s a bummer. Trump’s tariffs will only make this worse and interest rates are much higher now than in the 2010s.

My thought process

Full disclosure: I, personally, have a vested interest in this as my kiddo is districted for Jefferson, one of the schools targeted for replacement.⁵ I’m also a Portland city resident, and thus a local tax payer.

The case for the bond is pretty straightforward. We have a significant backlog of deferred maintenance for our schools. We have rebuilt the majority of high schools in the city and the majority of the money will go to finishing this job. We also live in the Cascadian Subduction Zone and an earthquake here will be Very Bad, especially for folks in buildings with unreinforced masonry (like, say, a school with a brick facade).

It’s mostly unsaid, but there’s an additional case for: delaying this work will only cost more money thanks to inflation/tariffs/rising interest rates. We’ll have to pay now or later; might as well pay now.

The case against the bond is a bit more complicated and different folks have different critiques. I’d say the come down to some combo of the following:

1. $1.8B is a lot of money!

2. Specifically, the $1.15B for the three high schools is a lot of money.

3. Enrollment is projected to decline significantly in the coming years.

4. The money is better spent on fixing up elementary and middle schools rather than the high schools.

5. There have been cost overruns with previous bonds and insufficient oversight/accountability.

6. There is not enough transparency in how the money will be allocated with this particular bond.

I would recommend reading the following endorsements to get a sense of the landscape:

• Mercury: Yes

• Oregonian: Tepid Yes, followed by a more enthusiastic yes

• Willamette Week: No

I waffled here a lot. I want money for infrastructure and a lot of these schools need the upgrade. I also had to look at a very big number and just sit with it while. It’s easy for very large numbers to wash over you so I wanted to consider that actual scope⁶ from first principles.

Assuming no change to what’s delivered, and assuming they basically hit their budget, what’s the difference between a $500M bond and a $1B, $3B, or $5B bond?

Would I vote yes for all of them? For none of them?

At $500M, the answer is obviously yes to me.
At $5B, the answer is obviously no.

Per the apocryphal Churchill quote, now we’re just haggling over price.

I know folks are worried about declining enrollment. Cities are dynamic, funny things and I’m not confident projecting out enrollment 10-20 years out. But I can look at the cost for the capacity of these schools and see if it makes sense.

Let’s go to the chalkboard.

Howard County, MD -

• My hometown just finished a high school build out. They broke ground in 2020, finished in 2023. Total costs were $143M for a 1,750 student capacity.

  = $81k per pupil

• Median income in Howard County is $68k and median home price is ~$667k.

Lexington, MA

• The most expensive HS construction on record, still in progress. Our local press will quote this as costing $662M but the actual price tag is now up to $695M.⁷ This is for a school that has a capacity of 2,400.⁸
  = $289k per pupil

• Median income in Lexington is $219k and median home price estimates vary but it’s between $1.6M and $2.5M.

Portland, OR

• Three high schools at $1.15B (+ the $366M already spent on planning fees) = $1.5B / 3 = ~$500M per high school, each with a capacity of 1,700.
  = $294k per pupil

• Median income in Portland is $47k and median home price is ~$545k.

So we’re talking about, on a per pupil-capacity basis, the three most expensive high schools in the country.

Why costs are so expensive deserves another post, which I don’t have the time, patience, or deep knowledge to write. Thankfully the Oregonian has a decent rundown. It’s a combo of green energy requirements, labor requirements, and (in my opinion) an unwillingness to make hard trade-offs.

How am I voting?

“Most expensive schools in the country” is a tough pill to swallow. And yet, were this the only chance to vote for a school bond in the next decade, I would probably swallow that pill and vote yes. The upgrades (especially the HVAC and seismic upgrades) are sorely needed.

Luckily for me, this isn’t the only chance. There will be a primary election in May of 2026. If voters shoot down the bond this time that should be more than enough time for the district to trim costs, perhaps even work with the city to eliminate expensive requirements. I’m confident they will try again soon enough.

I’m voting no on 26-259.

In the meantime, I pray the Big One waits for a few more years to hit.

1. I’ll leave that for next post.

2. You can also read this as: if there’s good evidence that it’s good for students then I’m for it, irrespective of what the Teacher’s Union thinks.

3. You can also read this as: fuck your signaling where you “center the voices of marginalized communities.” Show me the studies on how what you propose will actually improve outcomes for actually underserved kids. Or any kids, for that matter.

4. Even if he doesn’t wear a bike helmet most of the time. Which, actually, I’m totally fine with most of the time but I don’t think it’s great signaling for kids when you lead a bike bus.

5. She’s going into Kindergarten though. So PPS has a decade to figure this out before she walks through those doors.

6. Three High school upgrades, a bunch of deferred HVAC and Seismic maintenance, some new athletic and arts facilities

7. Original reporting here at Mortlandia. Source: my friend, a Lexington, MA elementary school teacher.

8. Note that modeling suggests that, just like with PPS, Lexington High is expected to be under-enrolled thanks to demographic decline. Rich people: they’re just like us!