A Portland middle school principal has apologized to her school community for an email she wrote to city officials criticizing two charter commissioners and saying they would be “done, gone and trashed” if they were not people of color.

“When I penned my email in June, it was intended to move beyond divisiveness to a position of collaboration; it was intended to facilitate communication, not to stunt it; it was intended to raise the level of dialogue, not devolve (it) further,” Lincoln Middle School Interim Principal Robyn Bailey wrote in a letter to the community that was shared with families Monday. “Unfortunately, I undermined the success of those women. I fell short on all accounts, I’m sorry.”

Bailey’s letter comes about two months after her email to the City Council and mayor was the subject of a school board executive session called as Superintendent Xavier Botana announced he was appointing her from assistant principal to interim principal at Lincoln. Executive sessions are confidential but former school board member Jeff Irish leaked details of what was discussed when he resigned this month. The emergence of the email prompted a backlash in the community and questions about whether Bailey is committed to the values of the district and fit to be a school leader.

“We simply don’t have the same racially charged issues as other big cities, but we are creating them,” Bailey wrote in the email.

In a separate letter to the Portland schools community Monday, Botana rejected Bailey’s comments and her assertion the city does not hold people of color accountable but stood by his recent decision to appoint her interim principal. Botana did not respond to emails or phone messages Tuesday seeking additional information.

“Once I became aware of the email, I met with Ms. Bailey to discuss her words,” Botana wrote in the letter. “She expressed remorse and an understanding of how her words in that email could be perceived as examples of unchecked biases. She affirmed her commitment to learn from this experience and take steps to restore the trust that was lost as a result of those words.”


Bailey’s original email came in June on the heels of elections for the city’s charter commission, a race in which her husband, William Bailey, ran for an at-large seat and lost. She did not respond to phone messages or an email Tuesday. City Councilor April Fournier shared Bailey’s email with school board member Roberto Rodriguez at the time, although he said it was sent to an email account he doesn’t regularly monitor, so he did not read it until August.

Rodriguez said Tuesday it was never his intent to harm or penalize Bailey, but he had reservations about her appointment as interim principal based on the content of the email and was seeking to make the superintendent aware so he could address them with her. The board was not voting on the appointments Botana presented at the meeting and no action was taken after the executive session to change them.

“We have a number of staff members that I believe are ready to take on a position like interim principal and when I told the superintendent I don’t have confidence in this appointment, my message to him was, ‘When we put people in leadership we need to be confident these folks can carry forward the charge of the Portland Promise, the comprehensive plan,'” Rodriguez said. “It’s me telling the superintendent what I always tell him, that these decisions, whether it’s personnel, the budget or anything else, need to be aligned with the comprehensive plan.”

During the executive session, Botana said Rodriguez drew attention to the comments Bailey made in the email about disparities and people of color being allowed to get away with statements for which others would be held accountable. “We have incontrovertible evidence that both of these premises are false,” Botana said in Monday’s letter. “Furthermore, they are patently inconsistent with the work that we have been engaged in as a school district for the past five years.”

In explaining his decision to move forward with Bailey’s appointment, Botana said the district supports employees’ First Amendment rights to express their views in myriad ways, including by writing letters to elected officials. He also said decisions around hiring, retention and promotion are based on how well employees do their jobs, as well as whether their performance and beliefs are in alignment with the values the district prioritizes.

Botana said the district requires ongoing professional development around diversity, equity and inclusion, and provides frequent feedback to staff to keep those issues at the forefront of their work.


“We are an educational institution and, as such, we believe in the importance of learning,” he said. “We believe that all of us are better than our worst moments. We believe in learning from our mistakes, which is an essential step in overcoming biases and prejudices.”

The two charter commissioners who were the subject of Bailey’s email said they have been disappointed by the district’s response.

“I will just say that for a school district with a stated commitment to diversity, equity and inclusion, they are falling short,” Commissioner Shay Stewart-Bouley said in an email. “In some ways, I am more bothered by Xavier Botana’s letter. It takes courage to be a leader and that means the ability to name things, even uncomfortable things and at this moment, his leadership seems lacking.”

Stewart-Bouley said she was not making a statement on Botana’s leadership overall, but just on the issue of the letter.

“What does this incident say to students of color in the district who are old enough to be aware of what’s going on?” she said. “Specifically what does this say to Black students and Black girls in the district? Personally, racism isn’t a learning moment, and should never be treated as such. To do so is to perpetuate the harm.”

Commissioner Nasreen Sheikh-Yousef said she wants a direct apology from Bailey, who she said has not reached out to her, as well as from Press Herald columnist Bill Nemitz for a column he wrote about the situation.


“As you can see, it doesn’t matter what people of color and I think and feel,” Sheikh-Yousef said in an email. “If it matters, they (would) not have moved forward with her appointment to the interim principal, (in a) school district that many students of color and immigrants attend.”

Soon after winning her seat, Sheikh-Yousef, who had previously been critical of City Manager Jon Jennings and described the city manager position as inherently racist, tweeted that Jennings is a white supremacist. Bailey did not name that tweet specifically in her email, but said comments by Sheikh-Yousef were “shameful” and “full of accusations and opinions.” She also took issue with tweets allegedly made by Stewart-Bouley, although Stewart-Bouley has denied Bailey’s characterizations on social media and her blog, Black Girl in Maine.

At the time, Bailey’s email raised concerns with at least one city councilor, Fournier, who forwarded it to Rodriguez, along with the message, “So disappointed and sad that this is someone who leads one of our schools.” In an Instagram post Oct. 7, Fournier said she shared the email with Rodriguez out of concern over the racial undertones she perceived in reading it.

“As a mother, an educator, a person of color and an elected official, I’m definitely concerned about the racially charged language and the message that was being conveyed in that email by someone who is a leader in our schools,” Fournier said. “The email denied that racism is a problem in our schools, but as the mother of four brown children who have gone through our schools and currently attend our schools, I can assure you there are lingering concerns from my children and myself that we have to address on a regular basis.”

The nonprofit Equity in Portland Schools also raised concerns about the situation in several posts on its Facebook page.

“Rightly, the School Board raised concerns about racist public comments from one of its vice-principals who was about to be promoted to interim principal,” the group said in one post. “An internal PPS process began to address the concerns, and the vice-principal in the meantime was promoted regardless. When resigned School Board member Irish leaked personnel information and made them public, he disrupted the process to address this complex, nuanced effort to respect their rights as a public employee, and appropriately address a racist act.”


Fournier did not respond to a phone message or email Tuesday. Equity in Portland Schools also did not respond to an email.

In her letter, Bailey said she has spoken with Stewart-Bouley and the two had an “open, honest conversation” in which they discussed how being able to have a voice is important. “I really wish someone had allowed me that same opportunity as I am the only one who can speak to my email,” Bailey wrote.

She said she learned a lot speaking to Stewart-Bouley, that Stewart-Bouley seemed to understand, and that she doesn’t want the June email to define her.

“I’ve had many difficult conversations, some with friends and some with people who don’t know me well,” Bailey wrote. “We are a strong community and significantly stronger together than divided. My door is always open to engage in dialogue about how we can do better. And I will continue to identify ways where our better angels can and should emerge as a community. Those are my commitments to this community and I wanted you to know that.”

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