Less than a month before the election, politics in Portland has reached a fevered pitch.

The tension – and some would say toxicity – of recent years between an energized, aggressive progressive movement and more moderate city officials spiked last week when a school board candidate suddenly dropped her re-election bid. Other city officials are also stepping aside, citing in part the political atmosphere. And former officials say the days of collegiality amid disagreement are gone and that officials are increasingly grouping into hardened factions, unwilling to compromise.

Portland Mayor Kate Snyder

City officials in Maine’s liberal largest city have been accused of not caring about people experiencing homelessness, even though they have agreed to pay up to $25 million to build a new homeless services center with wraparound services and a health clinic. They have been accused of being on the take from developers, even though they have passed moratoriums impeding development.

People who voice concern about city budgets and taxes are dismissed as privileged or even racist if they question anything labeled as an equity investment. Empathizing with concerns of small businesses makes one hostile to workers. And angry residents have shown up at or called the workplaces of some councilors to call them out.

“The pot has started to boil over,” Mayor Kate Snyder said. “It has become a bit unhinged. It is becoming untenable.”

Three city councilors not seeking re-election this year have said the political climate in Portland contributed.


The city manager, who was called a “white supremacist” by a member of the city’s charter commission on her first day in elected office, is leaving before the end of his contract. While interviewing for a similar position in Clearwater, Florida, Jon Jennings said the climate in Portland was so bad that his teenage daughter urged him to get a job elsewhere.

Sarah Thompson

Last Tuesday, when Sarah Thompson, a longtime school board member, dropped her re-election bid, she spoke of a political atmosphere that shuns collaboration in favor of strident ideology. What bothered her was the waning collegiality, not differences of opinion – which she acknowledged might fade over time if more people like herself walked away.

“It was really very hard for me to come to the conclusion I did, but I just find it’s taking more of a toll on me,” Thompson said. “If we’re all doing the same thing and all agreeing on the same things, we’re not representing the community as a whole.”

Jeff Irish

The very same day, school board member Jeff Irish resigned, less than a year into his three-year term, because of his discomfort with an executive session in which progressive members pushed back against the promotion of a principal. Their move was based on an email she wrote calling out two women of color on the charter commission and saying that Portland doesn’t have “the same racially charged issues as big cities, but we are creating them.”

Next month, voters will play a big role in determining the city’s future direction, with a third of the seats on the council up for grabs and no incumbents in those races. Meanwhile, an ongoing review of the city charter could soon prompt a radical restructure of city government.

Portland isn’t alone in its political shifts. Nationwide, local politics has become more heated. School board meetings have become the front line in battles over mask mandates and critical race theory. Before city councils, activists whose movements coalesced on crowded streets in last year’s protests are demanding local action, including slashing the budgets of police departments, in a nationwide fight to address longstanding injustice and inequity.


In Portland, progressives have thrived in the current political environment and pulled off a string of electoral wins, passing four referenda last fall and electing candidates to the school board, City Council and charter commission, which will issue recommendations that will then be subject to voters’ approval.

Kate Sykes at her home in Portland on Friday. Sykes is active in Portland’s progressive movement and is an organizer with the Maine Democratic Socialists of America. She believes elected officials have to develop better ways to engage with citizens face to face. Brianna Soukup/Staff Photographer

Kate Sykes, an organizer with the Maine Democratic Socialists of America and a board member of former Mayor Ethan Strimling’s “Swing Hard, Turn Left” group, said that the rhetoric can get harsh in Portland when people take to social media – which they do because there aren’t more authentic ways to engage leaders in political debates. The only way to get rid of that “violent communication,” she said, is for elected officials to develop better ways to engage with citizens face to face.

Former Mayor Ethan Strimling

When asked whether it was an acceptable tactic to foment political pressure on elected officials through email campaigns designed to spark citizens’ outrage, she said, “How do people participate otherwise?” She declined to comment directly on the current discussion of divisiveness in local politics, to which she and other progressives have contributed.

Sykes took to social media in 2019 after the council voted against a local paid sick leave proposal which it did primarily because a state-level proposal was on track for passage in the Legislature and would have trumped the local ordinance. She gave the dissenting councilors nicknames: “Crooked (Kim) Cook, Baby Vampire (Justin) Costa, Word Salad Spencer (Thibodeau), Deferential (Jill) Duson, and Whitey (Nicholas) Mavodones.”

Asked about similar jabs, Sykes wanted to focus on the positives – new people coming into office with new ideas, and expanded possibilities for real change given the increased awareness of systemic social problems that need fixing, not just in Portland but across the nation.

“We have a serious Overton Window shift in terms of our culture and our society, everywhere, not just in Portland,” she said, referring to a model that looks at the range of policies that the public is willing to accept at a given time. “And we need to be focusing our energy on a hopeful future.”


She noted that the DSA is not endorsing or campaigning for any candidates this cycle. “And I don’t feel this continued back and forth around ‘divisive politics’ in our newspaper is helping us get to a place that’s hopeful and community-building.”

Strimling, who over the summer urged the DSA to send out mailers opposing certain charter commissioner candidates, weighed in on Twitter on Thursday night.

“A lot of chatter right now about divisiveness in Portland politics,” Strimling said. “Make no mistake, the divide is not new. Nor the tactics. The difference is that those who are used to winning are now losing. And they don’t like it.”

City Councilor Belinda Ray

That doesn’t explain the elected officials who are walking away before losing elections. Some politicians say that campaign tactics such as fomenting outrage and demonizing those not in lockstep with purported progressive values is poisoning local political discourse and alienating people who may see the same problems but perhaps differ on the solutions.

“I am very happy to have hard conversations, but they’re not conversations when all you’re trying to do is shame somebody who doesn’t see it the exact same way as you,” said City Councilor Belinda Ray, who is not seeking a third term. “When you seek simply to shut them down, you end dialogue and you crush democracy.”

David Farmer is a Democratic political strategist, campaign consultant and Portland resident. Ben McCanna/Staff Photographer

David Farmer, a Portland resident and Democratic campaign strategist, sees a similar dynamic at play in both local and national politics.


Discussions about complex problems like homelessness and systemic racism are boiled down to buzzwords and talking points, he said, which are “accentuated by some pretty tough name-calling and rhetoric at times.” And policy disagreements quickly turn into questions about a person’s character or motivation.

“It’s not just that we disagree. It’s ‘you’re bad,’ and ‘you’re the enemy,’” Farmer said. “How can you compromise with the enemy? How can you compromise with the oppressor? How do you find a solution if you believe the other person is motivated by impure intentions?”

Portland City Manager Jon Jennings

Snyder and others point to the inception of Progressive Portland as the birth of a new political tone.

The group aggressively supported Strimling’s agenda and went to war against those who disagreed, sending inflammatory emails and action alerts.

It also began publishing an annual council scorecard, in which it declares the most and least progressive city councilors based on a few specific, cherry-picked votes.

Snyder said that has contributed to the us-versus-them, victim-versus-villain political atmosphere that she fears is tearing the city apart.


“It’s that Progressive Portland scorecard that basically declares that you’re either with us or you’re not. You’re either on the right side or you’re not,” she said. “I don’t believe you should arrive at the issues already knowing the answer, because you have to be willing to learn and have an open mind and work with your colleagues.”

Progressive Portland did not respond to an interview request last week sent through its website.

Snyder found herself getting called out on social media last week, after mistakenly sending candidate endorsements from home and on her own time through an emailing service that was connected to her city email account.

School Board Chairperson Emily Figdor took to social media to express her outrage, saying it was “a flagrant violation of city policy and possibly federal law. It’s why people rightly lose faith in govt & voting.” Another progressive activist, Jack O’Brien, echoed that on Facebook, telling the mayor sarcastically to “stay classy.”

A city attorney, meanwhile, said that section of the city’s personnel policy does not apply to elected officials. And Snyder owned up to the mistake and apologized.

Moderate Democrats have started to fight back. A political action committee, Unite Portland, was formed by former City Councilor Dory Waxman specifically to oppose Strimling’s re-election in 2019. And City Council member Tae Chong has taken to social media and the editorial pages of newspapers to push back against “progressive leaders” – though he seems to be borrowing from their playbook.


City Councilor Tae Chong

Chong recently posted on Facebook that school board member Roberto Rodriguez, who was born in Puerto Rico and is running for an at-large seat on the City Council, was actually white – at least according to how the U.S. Census defines race, he explained in an interview. He said he was trying to make the point that it was white school board leaders, not people of color, pushing the school board’s equity agenda.

Chong said he’s taken heat from progressive critics for misgendering an individual and for getting someone’s name wrong. He claims progressives would rather focus on those mistakes than debate the nuances of their policies, which he said are designed to make them “feel good.”

He argued that a $64 million bond approved by voters to renovate four elementary schools did nothing to address equity and that the new mandates in the Green New Deal for Portland passed by voters last fall will only further polarize new housing into luxury and low-income developments, with nothing for those in the middle. He also talked about how the hazard pay requirement in the minimum wage referendum passed last fall ended up stressing the budgets of nonprofits.

“I don’t care about what people say about me,” said Chong, pointing to his three decades of work on diversity, equity and inclusion. But as for the current style of politics, he said, “I’m sick of it. And that’s what I’m fighting so hard. I’m sick of that politics and I’m sick of people who have that mindset.”

Anne Pringle, a neighborhood leader in the West End, said local politics has become more ideological and partisan. When she served on the council in the 1990s, she said, councilors didn’t know one another’s party affiliations and were able to put policy disagreements behind them after the votes were cast.

Not so today, she said, when people are quick to make character judgments while claiming that officials are not listening to “the voice of the people.”


“People don’t speak with one voice. They speak with multiple voices that often differ from one another,” Pringle said. “And it’s the role of a city councilor to listen to all of those voices making a decision, and then explain it to the public.”

For others, the current upheaval is simply a changing of the guard, with longtime public servants questioning whether continued service is worth the headache and young progressives connected to the political machinery of interest groups eager to take their place.

That’s exactly what former City Councilor Kevin Donoghue sees happening on the school board.

“It’s uncomfortable, yet I see neither heroes nor villains here, just politics,” Donoghue said. “I know that serving in elected public office is stressful, especially in a time of significant change. Hopefully, elected officials can be compassionate with themselves and with others as they try to serve us best.”

John Anton, a former city councilor, said that the mixing of personal and policy conflicts is nothing new to city politics, which he described as always being “like a high school cafeteria.” It’s only more noticeable because of social media and local news coverage, both of which he said focus on conflict.

Anton said that the recent clashes – whether it’s Chong’s op-ed column accusing “progressive school leaders” of focusing on the wrong issues or recent school board resignations – are really about trying to influence the upcoming election.

“The balance of power is up in the air,” Anton said. “Political disagreements and personal disagreements are getting muddled up, and it’s just amplified by the current ways information gets out there. The shame of it is the substance, the important work that needs to be done, falls out of view when this happens.”

James Cohen, a former councilor and appointed mayor and past president of the Portland Community Chamber, said it’s up to voters to decide to make informed decisions at the ballot box, especially when it comes to local issues, which can take a tremendous amount of effort to become educated about.

“We all are responsible for creating an environment where negative campaigning works,” Cohen said. “That’s unfortunate. We all need to dig deep and reassess whether that’s the healthiest way for our government and society to function.”

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