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In April, Portland School Board Vice Chair Michelle DePass posted an intriguing blind item to Facebook. DePass recalled how a local elected official had approached her at a March 5 fundraising event and allegedly demanded a change to a Portland Public Schools policy that frustrated her family.
“Recently, I was approached at a party by a local elected official who wanted to shame me into making a special decision for her daughter that would allow the daughter to bypass the ‘rules’ about kindergarten entrance into her neighborhood school,” DePass wrote. “The elected official told me she thought it was an equity issue that the district wasn’t more flexible. She walked away saying ‘we just lost another PPS family’ before I had a chance to share that moving the rules for people who have access IS an equity issue.”
Who DePass was writing about is no mystery. Everyone familiar with the underlying encounter agrees it was Portland City Council President Elana Pirtle-Guiney. But what exactly the interaction meant is far less certain.
The district policy at issue requires that a child be 5 years old on or before Sept. 1 of an academic year to enter a PPS kindergarten that year. Born on Sept. 3? No luck.
Pirtle-Guiney says DePass misunderstood their conversation. In the council president’s telling, she was expressing alarm over a district policy that affected other families, not hers.
“My conversation with Board Vice Chair DePass was based on some emails [my family] got from PPS that raised a serious concern for me. We were told that kids whose birthdays fall around the kindergarten cutoff date could enroll in private school and then switch into PPS midyear,” Pirtle-Guiney tells WW. “That policy struck me as deeply inequitable: It’s not accessible to families in that situation who can’t afford private school. That is the point I made with her. And to be clear, my concern was not about my child specifically—any PPS policy change would have come too late to impact her.”
That last statement doesn’t appear to be correct, however. School Board Chair Eddie Wang says a policy change can “go into effect right away, or when the board members and superintendent say it will.”
For one elected official to publicly accuse another of trying to bend public policy to her family’s advantage would be noteworthy enough. But the allegation, which had been around for six months without anyone from the press taking an interest in it, also speaks to the way in which Portland Democrats have split into two camps—progressives and centrists—that each view themselves as sticking up for fairness and common sense against unreasonable adversaries in the other faction.
Pirtle-Guiney, a first-term city councilor whose wielding of the gavel as council president is increasingly a topic of debate as the presidential seat comes up for grabs in January, is perhaps the most high profile of Portland’s centrists—and understanding the background of the allegation against her isn’t possible without examining the tension between the two factions that have arisen in local government.
At the time Pirtle-Guiney spoke to DePass, the School Board was considering a policy change similar to the one she wanted.
Multnomah County Commissioner Julia Brim-Edwards, at the time a School Board member and chair of the board’s policy committee, pushed a change in policy this spring to allow families with soon-to-be 5-year-olds born between Sept. 1 and 30 to petition to enter kindergarten at a PPS school. She brought it up at the committee’s February, April and May meetings.
In fact, Brim-Edwards tells WW, she proposed the policy change after a conversation with Pirtle-Guiney at the swearing-in ceremony for councilors-elect on Dec. 19. It was their first meeting.
“She was like, ‘It’s odd because PPS is losing enrollment. Your kindergarten numbers have dropped, and it seems like PPS would want kids,’” Brim-Edwards recalls. She says Pirtle-Guiney was not asking for a personal favor. “She did not ask me to change the policy. She didn’t threaten me. She absolutely wasn’t asking for a special decision. I did it because I thought it was a reasonable thing, and PPS is bleeding students.”
The School Board had changed a more flexible version of the kindergarten entrance policy in early 2023 after district staff raised concerns that it favored more-affluent white families. Obtaining an exception to the birthday rule under that policy required an application, a costly readiness assessment, and a reference letter from a teacher. A staff memo in November 2022 called the policy “deeply inequitable.” Staff wrote: “This policy primarily supports the interests of a small number of white, middle or upper class families matriculating from private, tuition-funded [pre-kindergarten] programs.”
(Brim-Edwards’ proposal would not have ended the work-around that parents with means could send their child to private kindergarten and then transfer them to a PPS classroom midyear, which Pirtle-Guiney tells WW was her primary concern.)
Emily Glasgow, senior director of PK-5 academics at PPS, told the committee Feb. 26 that since the change in 2023, “there have literally been a handful of families who have reached out to us concerned. A handful meaning less than five.” Glasgow said she was “real hesitant to divert any staff resources to this small slice.”
That’s the context in which Pirtle-Guiney and DePass crossed paths at the March 5 annual fundraiser of the Center for Women’s Leadership. Attendees chose between blackened chicken, Thai salad rolls, and smashed frites for dinner.
There were no direct witnesses to the conversation.
DePass wrote about the conversation a month later. Under DePass’ Facebook post, commenters took competing views.
One of those who defended Pirtle-Guiney was Laurie Wimmer, executive secretary-treasurer of the Northwest Oregon Labor Council. “I know the situation of which you refer. With respect, that’s not the whole story. This family was EXPLICITLY told to seek private schooling…and then to transfer the child into PPS for first grade. That is unbelievable, given the declining enrollment financial challenges of the district, to say nothing of the best interests of the child,” Wimmer wrote.
In the comments, DePass dug in. “If it was me asking for my kids, this would be on the front page of the newspaper. Ethics and integrity matter.”
When contacted by WW, DePass declined to comment further on the interaction or her post. DePass is an employee of the Portland Bureau of Planning and Sustainability and during her tenure on the School Board has been one of its most progressive members. Last fall, she ran unsuccessfully for City Council in District 2—Pirtle-Guiney’s district—placing sixth.
School Board member Rashelle Chase-Miller, who was running for the board in March, stood just feet away from the DePass and Pirtle-Guiney conversation. She says she couldn’t hear exactly what was said, but she clocked the exchange as an unpleasant one.
She says DePass recounted the conversation back to her later that night. DePass’ telling of it matched her later Facebook post, Chase-Miller says.
“I was concerned about people that have power and influence working with other electeds—or trying to influence other electeds—to pass policy to their potential benefit,” Chase-Miller now tells WW.
Wimmer of the labor council says she spoke with Pirtle-Guiney about the birthday rule before her encounter with DePass and that there “seemed to be many dimensions of objection” to the policy. She says she rejects “the way that Michelle DePass was framing the conversation, accusing [Pirtle-Guiney] of using her privilege in an untoward way.”
If it is difficult to get anyone to agree what Pirtle-Guiney’s elbow-bending meant, that’s in part because who will control her gavel next year is top of mind for all city councilors.
The council will elect its next president at its first meeting of 2026.
Perhaps what best demonstrates the difficulty of the president’s job is that both the council’s progressive caucus, or “Peacock,” and its less-organized centrist bloc (no nickname as of this writing) have complaints about Pirtle-Guiney’s leadership.
Those complaints largely center on who gets to set the agenda at City Hall, either by chairing committees or getting a hearing for their policy proposals.
“Structurally, this council has basically spent a year dealing with Peacock’s stuff because they have chairmanships and majorities on these committees,” says centrist Councilor Eric Zimmerman. In other words, Pirtle-Guiney hasn’t reined in Peacock’s influence. (The council approved committee appointments by an 11–1 vote.)
Peacocks see it differently. They aired grievances in a group chat this spring that Pirtle-Guiney favored the centrists, and background conversations with five of the six Peacocks make it clear that frustration remains. “There’s a perception that she will use the bureaucracy to slow down your policies if she’s displeased with you,” Councilor Angelita Morillo says. But, Morillo concedes, it’s a tough job. “The president’s position is alienating. You’re in a position of saying no.”
Pirtle-Guiney says she’s “worked hard to ensure that policies that have been through the review in committee and met the deadlines are put on our council schedule as quickly as possible.”
Councilors on both sides of the centrist-progressive divide are sometimes frustrated by how inscrutable and careful Pirtle-Guiney is on the dais. Some ascribe it to her desire to remain professional and neutral as council president; others perceive it less favorably, calling her calculated and hard to pin down on her policy beliefs.
Pirtle-Guiney’s most complex and tender relationship is with Council Vice President Tiffany Koyama Lane, a member of Peacock. In response to WW’s request for comment about the DePass post, and Pirtle-Guiney’s leadership on the whole, Koyama Lane offered an oblique response.
“In positions of power, it’s important to stay aware of power imbalances that can exist and how our actions affect others,” Koyama Lane said, “especially behind closed doors.”
