The election of a commission to review Portland’s City Charter might be a low-key affair under more normal circumstances. Not this year.

A convergence of political forces, including impacts of the pandemic and demands for racial equity, has focused energy and attention on the new charter commission and the potential for historic reforms. It also has led to a profusion of lawn signs around town ahead of the June 8 election.

Three of the at-large candidates and a District 1 candidate have teamed up to run as a slate. The Rose Slate consists of at-large candidates Catherine Buxton, Patricia Washburn and Nasreen Sheikh-Yousef and District 1 candidate Shamika (Shay) Stewart-Bouley. The group describes itself as first-time candidates who support feminist values and collaborative politics.

Hope Rovelto has formally withdrawn from the at-large race, but her name will still appear on the ballot. Any first-place votes cast for Rovelto will be reallocated to the voter’s second choice.

Here is a look at the 10 active candidates for four at-large seats.



William Bailey

Bailey, a 52-year-old machinist, said he decided to step out of his comfort zone and run for the commission because many of the other candidates seemed to have the same agenda for changing the charter, including a push to a strong, executive mayor. He has his own opinions about city government, but says he’s not running to implement any specific agenda, but to provide balance.

“Everyone seems to be of one mindset – there needs to be a balanced viewpoint,” the Republican said. “I believe the focus should not lean too far in any one direction. Instead we need to hear from multiple perspectives and from many voices that make up a diverse Portland community.”

While emphasizing that he would keep an open mind about any topic, Bailey said he generally believes that Portland taxpayers are overburdened and would lean against proposals that would increase the size or cost of government.

He supports having a professional city manager to build the city budget and oversee the daily operations of the city, rather than an elected mayor. He doesn’t think being able to win an election necessarily qualifies a person to oversee the largest municipality in the state.

“(The mayor) might be a very popular person or a very nice person with the best intentions, but that doesn’t mean they have the skills to do that job,” he said. “I just think it’s dangerous.”

He doesn’t generally support expanding the number of city councilors, increasing their pay or adding any staffing positions.


“I am not in favor of enlarging government at all. If anything, I think it could be streamlined,” he said. “The taxpayers of Portland are overburdened as it is.”

For that same reason, he does not support a local public financing system for people running for the City Council or the school board, even though “at face value it sounds like a good idea.”

He said he doesn’t know enough about extending voting rights in municipal races to noncitizens, but he generally believes that citizenship should be required to vote.

Regarding the school budget, he said he supports the checks and balances, including the council review and voter approval.

In general, Bailey would like to bring common sense and an even keel to the commission.

“I’m not set in stone on any one subject,” he said. “I look forward to hopefully being able to sit at the able (and) listen to all viewpoints and make an informed decision and all come together and come up with something that works for everyone.”



Catherine Buxton

Buxton, a 31-year-old communications manager at Speak About It, a consent education and sexual assault prevention nonprofit, sees the charter review as an opportunity to make sweeping changes to the city’s governmental structure. Though she has her own ideas, she said her professional experience in violence prevention and education will help the commission design an inclusive process for all viewpoints.

“I spend lot of time brokering conversations with communities that don’t always agree with each other and I think that’s really important,” she said.

Buxton, a Democrat, would advocate for a strong mayor who has “more policy decision-making power” and a stronger influence over the city budget. She believes a professional manager or administrator would still be needed to help run daily operations, like in Westbrook. She said the commission would have to discuss how much power the mayor should have and whether that person remains part of the council. 

She envisions major changes to the council as well. She’s interested in converting at-large seats into district seats and redrawing the districts to better conform to neighborhoods. She’s also open to increasing the council from nine members to 12 or so and increasing their pay to make it possible for more working-class people to hold office, so they can spend more energy serving their constituents. Ideally, councilors would earn a full-time salary, she said, though she acknowledges the city has limited resources.

She is also interested in exploring neighborhood assemblies as a way to increase public engagement. The assemblies would be like neighborhood organizations, she said, only they would be elected by people in the district or appointed by councilors, and charged with helping district councilors solicit public input. 


She supports extending voting rights in municipal elections to noncitizens who live in the city. She believes that concerns previously raised by immigrant advocates, who worried that a separate voter roll for noncitizens could be used for immigration enforcement, can be addressed, since several communities in Maryland have safely implemented noncitizen voting. 

As a white woman, she would look would look to communities and leaders of color for ways to address any systemic racism in the charter. But she thinks the charter should require a staff position for diversity, equity and inclusion efforts, and mandate climate and racial justice impact statements for council policy, though she admits she would need more guidance on what topics are appropriate for the charter and which are policy issues for the council.

She supports creating a municipal clean elections program. 


Marpheen Chann

Chann, a 29-year-old activist/educator at the Holocaust and Human Rights Center of Maine, said he’s running because “we need open-minded, pragmatic people to help steer Portland toward a more vibrant and brighter future that is more inclusive and responsive, accountable and transparent, and fair and equitable.”

He said the commission’s most important task will be clarifying the roles of the elected mayor and professional city manager. However, he’s taking a more cautious approach than others, some of whom want to turn over budgeting and hiring decisions to a strong, executive mayor. He said City Hall services and operations should remain professional and nonpartisan.


Instead, he’d like to see the mayor be tasked with having a community dialogue to identify budget policies and priorities, and then packaging that for the city manager, who would be tasked with preparing a formal budget for the full council to consider. He’d also like to ensure that the mayor and council evaluate the manager on an annual basis, something that didn’t happen under the previous mayor. That way the manager would have to account for any priorities that were left out, adding a layer of transparency and accountability to the process, he said.

“They’re incremental changes that I think will have a big impact,” Chann said.

He’s open to the idea of eliminating at-large council seats and creating smaller council districts that better reflect neighborhoods. He also thinks that the mayor and council need to have staff to help conduct independent research of policy proposals.

He’d also like the commission to address racial justice and equity within the charter, beginning with land acknowledgement, stating that Portland sits on Wabanaki land and that it’s important to note the “painful and traumatic history of colonization.” He’d also like to explore requiring racial impact statements for policy proposals and establishing a permanent racial equity commission to advise the mayor and council. Such proposals should be embedded in the charter, he said, so they’re not subject to a change in political winds.

He supports public financing for municipal candidates. However, he would rather see the state’s Clean Elections program expanded to include municipal races, rather than requiring city taxpayers to pick up those costs.

He said he supports voting rights for noncitizens in theory, but such a proposal would need to be carefully studied. He is concerned about unintended consequences, such as people facing deportation for accidentally voting in a state or federal election, or by having the city’s voter roll of noncitizens fall into the hands of immigration authorities.


If elected as a commissioner, he would look for a collaborative process before recommending any changes, he said.


Lawson Condrey

Condrey, a 35-year-old project manager at the software consulting firm Fionta, said he’s running to make city government more accountable, accessible and transparent.

That begins, he said, with granting more executive power to the elected mayor, who should be setting the city’s priorities and driving budget discussions with the City Council. He thinks the city should have an administrator, hired by the council, to help run the daily operations of the city. He would like to see a model that emphasizes collaboration.

He believes that the council and the school board should have some staff to help analyze and develop policy.

“My guiding principle throughout all of this is making sure that the people who are making political decisions are the ones who are elected,” he said. “The administrator or manager is purely executing whatever the policy is that the mayor and council arrive at.”


Condrey said he’s most excited about expanding representation in city government. He would like to expand the council and create smaller council districts, which would make it easier to connect with voters and reduce the cost of elections.

“Right now it’s intimidating to get involved in Portland politics,” he said. “If a district is smaller, it lowers the barrier to entry.”

He doesn’t have a specific number of councilors in mind, but noted that converting at-large seats into new district seats would keep the council at nine members, who would be more closely connected to their constituents. He thinks the districts should be more aligned with the city’s established neighborhoods.

He supports a local public financing program for municipal campaigns and says that any local Clean Elections program should set aside a certain amount of taxpayer money for the mayor’s race and smaller amounts for district races. He also supports extending voting rights in municipal elections to noncitizens, many of whom have children in the school system and pay taxes.

He’s open to changes to the school budget process, but is not advocating for anything specific at this time. However, he worries that it could be confusing to have independent budget processes for the schools and city.

“I don’t know what the right answer is, but I’m open to discussion ’round that,” he said. 



Steve DiMillo

DiMillo, a 60-year-old lifelong resident and graduate of Deering High School, said he’s not running with any set agenda in mind. Instead, he’s looking to bring balance to the charter commission process.

DiMillo is the manager of DiMillo’s on The Water Portland, a family-owned business that also includes a marina and parking lot on the waterfront. He’s the chairman of the HospitalityMaine board of directors, a trade group representing restaurant owners and innkeepers. He described himself as fiscally conservative.

“I don’t think it should be as political as it is,” DiMillo, a Republican, said of the charter commission process. “I’m here literally to represent the citizens of Portland. I have lived here all my life and I feel a business-savvy person should be on the commission. I’m going to listen to everybody’s ideas.”

While many candidates are calling for more power to be vested in the popularly elected mayor, he said he hasn’t yet heard a compelling argument to replace the current system, which relies on collaboration between the mayor, council and professional city manager, who runs the day-to-day operations. He believes Mayor Kate Snyder is doing a good job, but questions whether even the current mayoral position is needed.

“I have not heard an argument yet that makes me want to (support) a popularly elected mayor executive – and I’m using that term loosely – someone who (is) calling all the shots instead of (the mayor) and (the manager) and the council working together,” he said.


He described the progressive activists who are pushing for a strong mayor as a “vocal minority” that is “very good at getting their message out.”

He believes it’s too easy for citizen initiatives to be placed on the ballot. He was the treasurer of the We Can’t Do $22 political action committee, which opposed the new minimum wage ordinance that was approved by voters in November. He said addressing referendums in the charter “is not on my agenda, but it’s on my radar.”

He opposes extending voting rights to noncitizens, saying that his grandparents were immigrants. “I’m a pro-immigration-done-the-right-way kind of guy. I love that Portland has this diversity, but it has to be done in a correct and legal way.”


Emerson, a 26-year-old Democrat who holds an English degree from the University of Southern Maine, said he was motivated to run because the pandemic laid bare structural inequities faced by working people in Portland.

Anthony Emerson

The grocery store cashier was upset the city ruled that a hazard pay provision in the voter-approved minimum wage ordinance would not take effect last December, as organizers intended. He blames the city and wants referendums to be more “iron-clad,” even though the city’s position was upheld in a lower court. An appeal is pending before the Maine Supreme Judicial Court.


“I felt like I really needed to throw my hat into the ring and stand up as the voice of the working Portlander – as someone who works and struggles in this city,” Emerson said.

“We need to think about what representation really is on the charter commission,” he added. “Most working-class people in this city making minimum wage are queer, many are people of color, many are women; we need to make sure our voices are also heard at the table when making these critical changes.”

He would like to make running for office easier. He supports a local public financing program for municipal races, by establishing a local Clean Elections program. He supports reducing the number of signatures needed to run for the City Council (currently 300 for an at-large race and 75 for a district seat). And he’d like to make it easier to place citizen referendums on the ballot.

“All of these are things that make it so difficult to really represent your community in municipal politics,” he said. “There’s such a high barrier. I barely made it because I didn’t have time to go out and collect 300 signatures.”

The number of district councilors should be expanded, possibly by eliminating at-large council seats and creating smaller districts that better align with neighborhood boundaries. Such a move would make councilors more responsive to constituent concerns, he said.

He believes the current city manager position holds too much policymaking power. Instead, he supports a strong mayor and city administrator form of government, like in Westbrook. He did not offer details about where the lines of authority should be drawn between the two positions. But he doesn’t envision a “Portland dictator.”


He’d like to cut the council out of the school budget process, allowing the school board to send its budget straight to the voters.

He also supports extending voting rights to noncitizens.

“I’m willing to sit down and listen to everyone basically on every issue,” he said. “I have my own views, but that doesn’t preclude me from listening to other people.”


Benjamin Grant

Grant, 43-year-old Democrat and attorney and partner at McTeague Higbee, said he’s running to reform the charter because he doesn’t think the system adopted a decade ago is working. He points to the increase in citizen referendums –six on last year’s ballot alone – and the City Hall infighting that occurred under the two previous mayors.

Grant has deep experience in state Democratic politics, including serving as party chairman from 2011-14 and executive director of the Maine Senate Democratic Campaign Committee from 2003-04. He also co-chaired the transition team and was a senior adviser for Gov. Janet Mills in 2018. He believes that experience will help inform the commission.


He supports creating a strong mayor system and removing the mayor from the council. The mayor should be empowered to craft and present the initial budget proposal, including the initial school budget, much like the governor does at the state level. That system, he said, will make it “easier to influence” and for residents to understand.

He said having the school and municipal budgets created and debated on separate tracks creates unnecessary friction between the board and council when the budgets are combined.

“I think it ultimately ends up shortchanging education in Portland because there’s almost this inertia around the two kind of silos,” he said. “The mayor is elected to presumably execute a vision that they ran on in the campaign, and they should be able to try to do that and not meet with a lot of resistance, at least at the outset.”

However, he would not make department heads, such as the finance director, political appointees to maintain a level professionalism and continuity in city operations. He’s open to reforming or eliminating the manager position and possibly having a city administrator. The mayor should have leeway in staffing decisions, especially with the hiring and oversight of the city administrator, provided that individual meets a certain set of qualifications. The council could have veto power over that hire and possibly others.

“The mayor should have some people that they bring (in) again within a certain boundary of qualifications,” he said.

The mayor should be the only person elected at-large and the election should occur during a high-turnout election, such as a gubernatorial or presidential election. He believes at-large seats on the council should become district seats that better align with neighborhoods. Such a system would make councilors more responsive.


He also thinks the council needs some staff to help with constituent services, including addressing complaints about potholes or other issues.

He also supports a local Clean Elections program and extending voting rights in municipal elections to noncitizens, since they’re impacted by the decisions of elected officials.

“I think the best type of city government is one that’s diverse, both racially and economically, and public financing certainly helps people run for office who might not otherwise do so,” he said.


Ian Pollis Houseal

Houseal, 42-year-old director of community development for the city of Sanford, is running because he believes his experience working in municipal government, including seven years working in Portland City Hall, would provide valuable insight and technical assistance in reviewing the charter.

He’s one of the few candidates in the race not advocating for a strong mayor system. In fact, he believes the mayor position should be a half-time job, rather than full-time.


“I think it would be a mistake to eliminate the administrative head of city operations and to have what’s called a strong mayor,” he said. “I think it would overpoliticize an overpolitized environment anyway and make it worse.”

He’s interested in creating a public advocate, or ombudsman position, to help people work through issues with City Hall and access needed services, such as General Assistance. He envisions the public advocate being an attorney working on behalf of city residents, rather than the council or City Hall.

The charter needs clarification around referendums, he said. While the referendum procedure is currently set by an ordinance and can be changed with a charter, he believes the rules governing citizen referendums should be set in the charter, which could set different standards for petitioning the City Council to take up a policy versus a petition to put an actual ordinance out to vote.

“I don’t necessarily think it should be more difficult,” he said.

He also thinks the charter can be an aspirational document for the city and outline a vision for environmental sustainability and other goals.

He’s open to changing the makeup of the City Council and school board, including eliminating at-large seats and creating smaller districts. He said he’d need to conduct more research before deciding whether the school board should have more budget autonomy, including the ability to send its budget directly to voters, without needing to go through the council.


As a naturalized citizen, Houseal said he supports expanding voting rights to noncitizens. He believes there are ways to address concerns raised by legal advocates about noncitizen voting rolls falling into the wrong hands. “We can keep a catalog that is inaccessible to other parts of our government. There’s absolutely ways to do that,” he said. 

He would also be interested in discussing whether the city should lower its voting age. For example, he said perhaps people as young as 12 should be able to vote in school board elections and maybe their vote should count as three-fifths of an adult’s vote.

He does not support a local Clean Elections fund, which would use taxpayer money to fund municipal campaigns. He doesn’t think it should cost a lot of money for candidates to introduce themselves to voters.


Nasreen Sheikh-Yousef

Sheikh-Yousef, 30-year-old progressive Democrat and community organizer, said she is running to focus on issues of racial justice. Although she is a member of Black POWER (formerly BLM Portland), she said her campaign is operating independently of that group.

Her top priority would be eliminating the city manager position and transferring those duties to the elected mayor, including the overseeing, hiring and firing of all city staff. She believes the manager has too much power to make decisions, especially when it comes to the city budget, and voters have no way to hold the manager accountable.


“It’s unfair to us Portland voters,” she said. “It makes no sense – there is no accountability. We elect our mayor to do that work.”

She wants to eliminate at-large seats and increase the number of district councilors. She’d like to pay councilors a full-time salary so they can devote more time to constituent concerns, without having to balance those duties with a full-time job. Councilors currently earn a stipend and serve part time, often in addition to holding a full-time job.

“It’s so hard to reach out to them,” she said. “I noticed that, when out campaigning, people are saying the same thing. And our mayor has no power.”

She supports clean elections, which is why voters were asked to create the charter commission in the first place.

She also supports extending voting rights in municipal elections to adult noncitizens, since many have children in the school system but are not allowed to vote on the school budget or elect councilors or school board members. And many noncitizens have jobs, own businesses and pay taxes, she said.

She thinks there are ways to address concerns raised by immigrant advocates, who worry that a special voter roll for noncitizens, which would be needed since noncitizens cannot vote in state or federal elections, could be used by immigration enforcement. Additionally, she said noncitizens worried about immigration enforcement could choose not to vote.


One topic she is interested in exploring in the charter review is defunding the Portland police and reallocating that funding to other community groups. She would also like to increase citizen oversight of the police, though she’s not sure if the charter is the appropriate way to do that.

“I’m still learning about the charter commission and what I can do if I get elected to the charter and what I can’t do,” she said.

On the school side, she would like to eliminate the City Council’s role in the school budget and instead allow the elected school board to send its budget directly to voters.

“It does not make sense why it has to go to the City Council,” she said. “They have no knowledge of it. I don’t support that system.”


Patricia Washburn Photo by Jen Dean

Washburn, a 56-year-old Democrat and senior copywriter at Aetna, said she’s running for the charter commission to advance equity and address systemic racism in the city charter. But she acknowledges that she’s a “white woman raised in a racist culture,” so listening to the community will be important.


“I’m doing this because I want to be part of the solution to structural racism in the city,” said Washburn, who co-founded Progressive Portland but has not been involved with the group since 2018. “I am committed to listening to and supporting populations of color in building a better city.”

Her top priority would be eliminating the city manager and shifting those powers to a strong mayor, who would run the daily operations of the city, perhaps with the help of an administrative deputy. She noted that the Ku Klux Klan supported the change from a strong mayor in 1923 to a city manager-council form of government.

“It’s important to do this and remove the influence of Ku Klux Klan from our city’s structure as a symbol and part of a real commitment of uplifting people who are not white,” she said. 

She would also advocate changes at the City Council and school board.

She would eliminate at-large seats from the council and expand it to include 13 district seats, or to “some other reasonable number” that better resembles city neighborhoods. She said if she were to run for the District 1 seat, she would need to campaign both on the peninsula and the islands. She said it can be difficult to represent mainland and island residents, because they have different interests.

“I think the other districts are equally large and unwieldy,” she said.


She would like to increase council pay, possibly providing a full-time salary so councilors can devote more time to responding to constituent concerns. The current structure makes elected officials only available to more affluent families, she said. If one is not affluent, she said, the low pay makes councilors susceptible to corruption and open favors or services in exchange for policy votes, though she quickly added, “Not that I’m accusing anybody of taking up this temptation.”

“You’re open to people offering you the money you’re not making as a councilor,” she said.

She supports extending voting rights to all adult residents, including noncitizens, because many noncitizens pay taxes and have children in the school system but are unable to vote on the school budget or elect school board members or city councilors. That would have to be done with input from the people impacted, she said.

“I’d like to explore whether it’s possible,” she said. “If it’s a really bad idea, we should drop it.”

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