City Cast Portland logo

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

The Weekly Wander by City Cast PortlandMay 10

Side Quest: Inner Peace

The Vedanta Society of Portland, founded 100 years ago, is based in Mt. Tabor, but the group also oversees the Vedanta Retreat — 289 acre...

A large wooden eagle structure made in a Native American style is nestled among soaring evergreen trees at the Vedanta Retreat outside of Scappoose, Oregon.
The Weekly Wander by City Cast PortlandMay 10

Your Guide to Mt. Tabor

For a neighborhood built on and around an extinct volcano, Mt. Tabor is remarkably peaceful. You won’t catch a whiff of fire and brimston...

Looking west from Mt. Tabor, grass and yellow flowers sit in the foreground with evergreen trees and a filled reservoir beyond. Portland’s distant skyline can be seen on the horizon under an overcast sky.
Portland's BestApril 30

Your Guide to May 2026 in Portland

From Mother's Day brunches to 503 Day celebrations to the Primary Election, there's going on in Portland this month.

People on a podium having shot off confetti.
Food & DrinkApril 7

Where To Find the Best Deals for Portland Groceries

For the last year, Stumptown Savings’ Bryan M. Vance has been tracking where to find the cheap groceries in Portland. His one-person medi...

A grocery store aisle.
Portland's BestApril 1

Your Guide to April 2026 in Portland

Out on the Oregon Coast, April means it’s time to celebrate the puffin’s seasonal return to Cannon Beach, which will host an annual Puffi...

A closeup of a tufted puffin.
Portland's BestMarch 16

Where to Find Downtown Portland's Best Hotel Bars

With the opening of Damian Lillard's shiny new bar at the Benson Hotel, I've been thinking a lot about our city's hotel bar scene. For me...

people sitting curved banquettes and tables, at Abigail Hall, Portland, Oregon
Portland, ExplainedMarch 12

How Well Do You Know Portland?

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...

couch street sign
Portland, ExplainedMarch 10

The Portland Area’s Local Income Taxes, Explained

Here’s a reminder on all our local taxes due today: The Portland Arts Tax, Metro Supportive Housing Services, and Multnomah County Presch...

Cropped shot of Asian woman sitting at dining table, handling personal finance with laptop.