City Cast Portland logo
Advertisement image

Your Guide to May 2025 Special Election

Posted on May 14, 2025   |   Updated on September 30, 2025

Rachel Monahan

front of a brick high school building

Will Portland voters approve a modernization of Cleveland High School? (Rachel Monahan / City Cast Portland)

Surprise! There’s a May special election.

If you’re anything like me, you probably haven't filled out your ballot yet.

The good news is, this election is nowhere near as complicated as it was in the fall: You won’t be ranking your choices, and there are fewer decisions. And yet there are some key issues and candidates to decide between — including a major bond for Portland Public Schools.

If you don’t have your ballot, call the elections office for a replacement (Multnomah County: 503-988-8683, Clackamas County: 503-655-8510, or Washington County: 503-846-5800). (This close to the election, you may need to vote in person.)

⚠️ The deadline: Drop your ballot in an official ballot box by 8 p.m. next Tuesday (May 20). Or get it postmarked by that date.

Measure 26-259: Portland Public Schools Bond

Portland Public School is looking to raise an estimated $1.8 million to overhaul Ida B. Wells, Cleveland, and Jefferson high schools, as well as some other projects.

🗳️ What’s on the Ballot:

✅ A yes vote passes the bond.

❌ A no vote would not.

Background: Since 2012, the district has been working down the list of high schools that need modernization. This bond would complete the last three — and provide technology as well as other upgrades for schools. (A bond doesn’t cover ongoing expenses, and will do nothing for the budget shortfalls the district is currently facing.)

If passed, property owners would continue to pay $2.50 per $1,000 of assessed value that they have previously supported for past bonds. (The district expects there will be no more costs.)

✅ The argument for it: Portland’s schools were mostly built more than 75 years ago and are in need of an update — not to mention a seismic upgrade.

❌ The argument against it: Opponents argue the district has failed to complete the work funded by the previous bond, including the Center for Black Student Excellence. They also say the current designs for the high schools are too expensive — and too big — given that PPS’ enrollment is declining.

🥊 Editorial positions:

  • No says Willamette Week
  • Yes (“under duress”) said the Oregonian, before revising to a “strong yes
  • Yes says the Portland Mercury

🗞️ Further reading:

If you read one more thing on the bond, check out OPB’s comprehensive rundown of the issues: “Late to the party? Here’s what you need to know about Portland Public Schools’ 2025 bond.”

🗳️ Other issues:

As always, the voter’s pamphlet is surprisingly informative. Here’s your reading for Multnomah County, Washington County, and Clackamas County.

City Cast

The Gigantic PPS School Bond on Your May 20 Ballot. Plus, Our Listener Mailbag

00:00:00

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

Local Civics

See All
Local CivicsFebruary 10

$106M in Unspent Funds at the Portland Housing Bureau

The Portland Housing Bureau has $106 million in unspent funds, the city administrator disclosed late last week. Some of it may be spoken...

City Hall, Portland, Oregon
Local CivicsJanuary 28

The Gas Tax and Oregon's Legislative Session

State lawmakers convene in Salem next week after a chaotic few weeks for Democratic state leaders as they scramble to address the issue o...

Oregon state capitol with cherry trees, Salem, Oregon
Local CivicsNovember 12, 2025

US Sen. Wyden Explains His Votes To Arm Israel

Oregon’s U.S. senators usually vote the same way (like for continuing the government shutdown until healthcare costs are addressed). But...

U.S. Senator Wyden in blue suit and tie stands outside the U.S. Capitol building near columns
Local CivicsOctober 23, 2025

The Portland Parks Levy on the November 2025 Ballot

The Parks Levy 2025 Ballot Initiative (Measure 26-260) would raise some $456 million over the next five years.

pond in the middle of Laurelhurst Park, Portland, Oregon
Local CivicsJuly 2, 2025

What Passed and What Didn't in Salem This Year

After the Legislature failed to pass new transportation funding, the Oregon Department of Transportation is expected to lay off workers.

Oregon State Capitol Building
Local CivicsJune 9, 2025

Portland Mayor Keith Wilson Has a Plan to Fund Both Parks and Police

Mayor Keith Wilson, a trucking company entrepreneur turned politician, sat down with the City Cast Portland podcast to discuss his first...

Mayor Keith Wilson in white pullover sweater leaning against a wall, the blurred vision of sidewalk behind him.
Local CivicsJanuary 22, 2025

What's the Deal with Portland's $100M Budget Shortfall?

Portland’s budget office announced last week that there’s an expected $100 million shortfall going into the next fiscal year, which begin...

City Hall in Portland, Oregon, with an image projected on the front
Local CivicsNovember 20, 2024

What Actually Happened With Portland's First Use of Ranked Choice Voting

Two Portland City Council races are still up in the air, as the third councilor has yet to win decisively in Districts 1 and 4: In East P...

Ballot drop box, Multnomah County, Oregon

The latest in Portland

Summer GuideJuly 30

Tips for a Better August 2026 in Portland

August is our hottest month, so we all need to figure out how to stay cool in Portland - check out a few tips we've gathered.

The Oregon coast with haystack rocks off the shore and a wide beach.
Portland, ExplainedJuly 30

Test Your Knowledge of Portland Art

You can tell whether you’re a real Portland resident by how you pronounce local names. Or can you? Today’s quiz tests your Portland stree...

elk statue next to a tree, with high-rise buildings in the background
Portland's BestJuly 30

What To Do in Portland in August 2026

We have some ideas for how to make this month in Portland more exciting, easier, and just an all-round good time.

Green fish or shark like head with pointy teeth and a tongue hanging out is this soapbox derby entrant. People and a van and trees in the back.
Summer GuideJuly 27

The Most Overrated (and Underrated) Portland Summer Activities

Summer in Portland often feels ideal — the weather is mostly moderate, and there's an endless list of events and outdoor destinations to...

A mossy and rocky terrain with a steep cliff covered in trees in the background.
The Weekly Wander by City Cast PortlandJuly 26

Side Quest: Stop and Smell the Roses

Although you’ll now encounter a multi-hued oasis, when the garden opened in 1913, it was planted with nothing but fragrant, pink roses.

Two people walk their bicycles through an ornamental rose garden, popping with vibrant red, pink, and white blooms.
The Weekly Wander by City Cast PortlandJuly 26

Your Guide to Piedmont

Piedmont is perhaps Portland’s oldest planned community, with a deed dating back to 1889.

Hundreds of people sit on the lawn in front of the historic gazebo in Peninsula Park.
The Weekly Wander by City Cast PortlandJuly 19

Side Quest: Second-Run Stars

Portland’s historic movie theaters are time capsules of cinema-how-it-was, and watching modern films somehow feels less soul-sucking.

Cars are parked on the street outside of Academy Theater in Portland’s Montavilla neighborhood. The blue facade is cylindrical with a marquee lined by blue lights.
The Weekly Wander by City Cast PortlandJuly 19

Your Guide to Montavilla

Long a stopover for travelers between Hood River and Portland, Montavilla is a crossroads of cultures and camaraderie, and every summer,...

Crowds of people browse the stalls at the Montavilla Street Fair. Booths can be seen on both sides of the street.