With the 2018 election in the books, all eyes in Portland now turn to next year’s mayoral race.

Last Monday, one day before Election Day, incumbent Mayor Ethan Strimling filed initial campaign paperwork at City Hall that allows him to begin raising and spending money on things like polling. His filing is well ahead of former Mayor Michael Brennan’s registration, which wasn’t filed until the June before the 2015 election.

Strimling said the filing doesn’t necessarily mean he will seek re-election.

“I’ll make a final decision on running by the end of spring,” Strimling said. “(I) filed the paperwork to make sure everything is copacetic as I begin exploring.”

Ethan Strimling

Although no other candidates have declared, several city councilors may throw their hats into the ring. Those exploring potential runs are Councilors Spencer Thibodeau, Belinda Ray and Justin Costa. And since the city uses ranked-choice voting in its mayoral election, the door is also open to outsiders, especially those who have name recognition. The first mayoral election in 2011 drew 15 candidates.

Having sitting councilors in the mix will make for an interesting dynamic this year, since Strimling’s first term has been marked by high-profile clashes with the City Council and City Manager Jon Jennings.

Strimling has spent much of his first two years debating the council and attorneys about his scope of power and whether he should have an assistant. At one point, he suggested creating a task force to opine on the issue of mayoral power, but never followed through.

Over the last year, however, that debate has subsided, at least publicly. After helping pass a $64 million bond to renovate four elementary schools and passing a local property tax rebate plan for seniors, Strimling has focused more on advancing policies such as earned paid sick time and responsible contracting rules. He’s also trying to persuade councilors to borrow $7 million for unidentified affordable housing projects.

The mayoral election is likely to add a level of tension to the relatively routine, yet important, process of establishing council committees. Those members will be appointed next month by the mayor, but the council has the power to override those appointments.

Last year, the appointment process devolved into an all-out battle when Strimling tried to appoint himself chairman of the Finance Committee – a move that was rejected by an 8-1 council vote and led to a monthlong delay in establishing council committees and goal-setting, giving councilors less time to grapple with issues. Strimling said he hired an outside attorney using $500 in leftover campaign funds to assist him during that debate.

This will be the city’s third mayoral race since switching from a ceremonial mayor, who was appointed annually by the council, to a popularly elected mayor, who serves a four-year term, as opposed to three-year terms for councilors.

The mayor’s position is decided by a citywide vote using ranked-choice voting and instant runoff tabulations until someone wins more than 50 percent of the vote.

The mayor earns a full-time salary but does not have any executive control over city operations, which are overseen by the city manager.

The City Charter says the mayor must be paid a minimum of 1½ times the median household income for Portland, as determined by the U.S. Census Bureau, but that does not preclude the mayor from earning more.

The charter calls on the council to adjust the salary prior to nomination papers becoming available for the mayor’s position, but that did not occur in 2015, while also allowing the council to adjust it during a mayor’s term.

Strimling, who earned $73,000 in 2017, requested a salary review earlier that year, but the council delayed the discussion for at least a year. The council has not revisited that conversation since then and did not have it prior to the 2015 election.

The city’s first mayoral election in nearly 90 years was held in 2011. Strimling was defeated by Michael Brennan in a 15-way race that required 14 rounds of instant runoff tabulations before a winner was crowned. But four years later, Strimling, touting endorsements from almost every councilor, school board member and many former city officials, beat Brennan in a three-way race that was decided in the first round of voting. Strimling didn’t announce his candidacy until August, though polling was conducted by Bob Baldacci and Baldacci Communications on his potential candidacy earlier in April and June of 2015. Baldacci Communications later worked for Strimling’s campaign.

If history is any guide, whoever runs against Strimling should be prepared to raise money. And a lot of it.

In 2015, Strimling raised a staggering $117,537, including $16,275 from out-of-state donors from 15 states – from New York to Florida to Texas to Arizona to California to Washington. In the final 11 days, he raised over $17,000 and spent over $50,000 to make his closing arguments to voters.

However, a bulk of that money was raised from developers and the business community, whom the mayor has since found himself lined up against.

His 2015 campaign reported an $11,490 balance in its 42-day post-election report. Later that year, he paid an additional $4,000 to Baldacci Communications, $1,500 to the city-owned Barron Center for food for his inauguration party and $2,500 in fundraising fees.

Last fall, Strimling made an $800 contribution to Protect Our Neighborhood Schools, but that donation is expected to be refunded, since the state ethics commission staff has informed Strimling that surplus campaign funds can go only to other candidates and political parties, not PACs. He also paid $500 to Jensen Baird Gardner & Henry right before the new year to advise him during his debate with the council about committee assignments.

After those expenses and monthly banking fees, Strimling had $1,700 on hand, according to his July 2018 semiannual report.

Several sitting councilors are expected to try to unseat Strimling. If successful, it would be the first time the city had an elected mayor come to office after having experience as a city councilor. Both Brennan and Strimling previously served as state legislators, but not at the council level.

Thibodeau, who just won re-election for a second term in District 2 by a 2-to-1 margin, said he’ll use the next few weeks to talk to supporters about making a possible run. He currently leads the council’s Sustainability and Transportation Committee and serves on the Economic Development Committee.

“There’s no question I’m going to take a hard look at it,” Thibodeau said. “I think Portland is definitely ready for a change at the top.”

Ray’s name is also being tossed around, but she declined to talk about next year’s mayor’s race, since she just finished a successful re-election to a second term for District 1. She leads the Health and Human Services and Public Safety Committee and serves on the Sustainability and Transportation Committee and the Rules Committee.

“It’s too early to be talking about it,” Ray said. “The election signs aren’t even down yet.”

While Ray and Thibodeau already have built-in constituencies on the peninsula, where more progressive candidates like Strimling tend to do really well, District 4’s Costa is another potential candidate. A year into his second term, Costa has served longer than Ray or Thibodeau, including a three-term stint on the school board, and has a base constituency off-peninsula, a key demographic in a citywide race.

“I’ve been approached and asked to run for mayor by several people in the community who have served and who haven’t served,” Costa said. “I will think seriously about it and make a decision sometime early next year.”

At-large councilors, who have a demonstrated ability to win citywide elections, are also potential challengers, but none seem particularly eager to run – at this point, anyway.

Councilor Pious Ali said he will seek re-election to his at-large seat next year and Jill Duson, who faced a tough re-election bid in 2017 and made an unsuccessful bid for the Democratic nomination for state Senate this summer, said it was too soon to be thinking about next year.

Nicholas Mavodones, who narrowly won re-election against Joey Brunelle on Tuesday, did not respond to a request for comment.

Brunelle, who has been campaigning citywide for most of the last two years, laughed when asked by a reporter if he was considering a run.