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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

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