Oh, the irony. For all their talk about reforming law enforcement, Portland’s progressive leaders are fast becoming the language police.

This week’s dust-up over two departures from the Portland Board of Education – longtime member Sarah Thompson abruptly ended her bid for re-election, while newcomer Jeffrey Irish resigned after one year in office – has all the trappings of an elected body mired in dysfunction.

Their beef: The school board, chaired by Emily Figdor and dominated by fellow members of Portland’s self-described progressive movement, has come down with a bad case of lockstep. If you’re not 100 percent with them, as Thompson put it to Press Herald reporter Rachel Ohm on Tuesday, “you’re automatically the enemy.”

Tough words, to be sure. But wait, there’s more.

Announcing his resignation on the heels of Thompson’s surprise withdrawal, Irish laid bare an incident that was, in a word, chilling. In an executive session on Aug. 17, he said board members discussed whether a newly appointed Portland school principal was the right fit for her job because she had the gall to question, in a personal email, what the local progressive movement is doing to her city.

It all started on June 10, when Robyn Bailey, then-assistant principal of Lincoln Middle School, emailed Mayor Kate Snyder, members of the City Council and City Manager Jon Jennings in the immediate wake of Portland’s charter commission election. Bailey copied me on the email.


In it, she said the tone that had been set by progressive candidates who’d just been elected to the commission was “downright rude, disgusting and should not be tolerated.”

Specifically, Bailey cited repeated claims by commission member Nasreen Sheikh-Yousef that the city manager was a “white supremacist.” Bailey also took issue with commission member Shay Stewart-Bouley’s “tweets about sodonmy (sic), her hatred of white people (and) her covid pounds in relation to her breast size.”

Bailey continued, “I am embarrassed for me, you and as an educator I am not sure how I explain all this to the middle schoolers I work with. My families would not tolerate such behaviors from me, nor should they have to. I work FOR them. These newly elected people need to do better.”

Then she crossed over into what some in Maine’s largest city might consider political heresy: “No one wants to hear my next words, but we all know that if the people saying these things were NOT people of color, they’d be done, gone and trashed. Please hold ALL people accountable for their words.”

As Ohm reported on Thursday, the email was forwarded in June from city Councilor April Fournier to Roberto Rodriguez, a member of the school board and currently a candidate for city council.

That’s when things got sticky. Shortly after Superintendent Xavier Botana informed the board in August that Bailey had been appointed interim principal at Lincoln Middle, Rodriguez moved to go into executive session. There, according to Irish, Rodriguez read Bailey’s email aloud and then urged Botana to reconsider her promotion to interim school principal.


At the same time, Irish said in his resignation letter, “five other members of the board who have never met the appointee, all agreed that an educator with over 20 years of exemplary service does not reserve the right to express their private opinion while climbing the professional ladder when their perspectives do not align with the board.”

The good news for Bailey is that she was not fired, demoted or otherwise disciplined. Still, the board’s closed-door deliberation sends an ominous message: If you’re going to work for us, you should think twice about criticizing our political allies.

In a brief telephone conversation Thursday morning, Bailey made it clear that the board’s message had been received. “I am not going to say anything at this point, as you can imagine,” she said.

No surprise there. But a few questions remain.

Was it right for the school board to discuss Bailey’s email in an executive session, where they were free to critique her politics without a pesky public audience? Superintendent Botana said earlier this week that the session had the blessings of the school department’s attorney – a dubious call at best. But now-former board member Irish raised a valid point when he noted in his letter that the private discussion “better resembled a safe space for someone who felt hurt about another’s opinion.”

Another question: Does Rodriguez, who sat on Bailey’s letter for two months before pouncing on the night she was promoted, understand the difference between personal politics and his public conduct as an elected official?


Rodriguez told me in a telephone interview on Thursday that he asked for the executive session not to go after Bailey, but rather to confront Botana for promoting someone to a leadership position when, in Rodriguez’s opinion, she appeared not to be in line with the school department’s racial equity goals.

“If I see a communication from a staff member that there are no (racial equity) problems in our schools and nothing needs to change, then I wanted to express to the superintendent that I did not have confidence in this person’s ability to advance the work that I have charged (the superintendent) with doing,” Rodriguez said. “This was me holding the superintendent accountable.”

One problem there. Bailey never said in her email that there are “no problems” regarding racial equity in Portland’s school system. What she did say was that “we simply don’t have the same racially charged issues as big cities, but we are creating them. We don’t need to undo our educational system the way we are, we already have teachers who are teaching perspectives without alienating their students or their families.”

In short, she was exercising her right as a citizen to free speech. I asked Rodriguez: Might other city and school employees, having watched Bailey’s email lead to an executive session over whether she’s the right person for her new job, feel squeamish going forward about speaking their minds to their elected leaders?

“You know what? That’s a really fair question,” Rodriguez replied. “And yes, I’m aware of that. This is a reality and I acknowledge that that’s the case.”

OK, then. If preemptively muzzling those on the city’s payroll who see the world differently than those in charge is the cost of doing business, then so be it. Talk about oppressive work rules.


Finally, beyond the school board drama, where exactly is Portland’s government headed?

At last count, the city manager, police chief, three city councilors and two school board members have either departed or announced their plans to do so soon – virtually all of them having crossed the progressive powers that be in one way or another.

Simultaneously, groups like Progressive Portland and the Maine Democratic Socialists of America are poised to strengthen their grip on both the City Council and school board in next month’s election, while at the same time aiming to overhaul the city charter to align with myriad far-left goals.

My prediction: Portland will find itself immersed in political turmoil for the next three to five years before the pendulum swings, as it always does, back to a place where its working motto is no longer “our way or the highway.”

In the meantime, if your paycheck comes from the city and you happen to have a problem with the current state of affairs, you’d best be watching what you say.

FOOTNOTE: While writing this column, I did not reach out to Shay Stewart-Bouley, a member of the Portland Charter Commission, to discuss Robyn Bailey’s concerns about a post by Stewart-Bouley on Twitter. In retrospect, I should have and regret not having done so.

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