Cheryl Leeman for mayor?

I suspect we haven’t seen the last of Cheryl Leeman, the Portland city councilor who’s ending her three-decade run this year. She’ll be serving until her successor is sworn in a couple weeks after Election Day, but one refers to Leeman as a “lame duck” at their peril — she’s as fired up about what’s happening in city government as she’s ever been.

That’s one clue to her future political plans. Another is her stock reason for leaving: to “spend more time with family.” Leeman, who’s in her mid-60s and divorced decades ago, retired from her position as Sen. Olympia Snowe’s regional representative in late 2012, after the senator herself called it quits, and it’s hard to believe she’s had trouble scheduling quality time with her two grown children since then.

But the third clue is the big one. As I detailed in a profile of Leeman for the September issue of The Bollard, as far back as the late 1970s, she’s jumped into the political fray pretty much every time her neighbors have asked her to.

When city officials wanted to widen Washington Avenue to four lanes, concerned parents huddled around Leeman’s dining room table to plot an alternative (which the city reluctantly accepted). When school officials planned to close Presumpscot Elementary School, in Leeman’s East Deering neighborhood, her house again became headquarters for the opposition, which turned that plan back, too. Realizing they needed a voice on the school board, the parents turned to Leeman, who was operating a daycare out of her home at the time. She ran and lost, then ran again, won, served a three-year term on the board, and won her city council seat in 1984.

Since Leeman announced earlier this summer that she won’t seek reelection this year, people have approached her “every day,” she said, urging her to run for mayor next year. Tellingly, she has not ruled it out. Frankly, I’d be surprised if she didn’t run.

The timing is perfect. Freed of her duties as a district councilor, but far from forgotten, Leeman can take a few months off to strategize, then begin building support for a mayoral run next spring.

photo/Patrick Lynch, courtesy The Bollard

photo/Patrick Lynch, courtesy The Bollard

Leeman’s primary disadvantage, should she decide to run, is the fact she’s a registered Republican in a city where such creatures are scarce — if not endangered, given the animus toward the Republican in the Blaine House these days. One Portlander I spoke with regarding Leeman’s potential candidacy imagined a “nightmare scenario” in which Republicans lead the governments of Maine and its largest city. (Portland’s city council and mayoral elections are officially nonpartisan, but if you believe that, I have a bridge to South Portland I’d like to sell you. )

That said, Leeman proclaims herself more an independent than a party loyalist, just like her former boss, and most city issues don’t have a partisan angle. Those that do could hurt incumbent Mayor Mike Brennan (assuming he seeks reelection) more than Leeman.

For example, while Leeman’s kicking back enjoying “family time,” Brennan will be fending off kicks over his proposal to raise the city’s minimum wage. Most of the business community will be unhappy if the wage is raised at all, and progressives are already complaining that the figures being floated by the advisory group Brennan formed aren’t high enough (topping out at $10.68/hour in 2016; far from the $15 die-hard activists are demanding).

There’s also the fact that Leeman’s council district, which includes East Deering, Back Cove and parts of Deering proper, is filthy with Donkey Party members who have consistently elected her by wide margins.

Leeman’s primary advantage is her experience. Nobody in City Hall, elected or otherwise, has the institutional knowledge she’d bring to the job. What’s that kind of knowledge worth? Well, add up the cost of the string of court battles the city’s lost in the past year fighting panhandlers, anti-abortion activists, and the Friends of Congress Square Park (who won a judgment last week that obligates the city to pay their attorneys’ fees, to the tune of over $50,000), and you’ll quickly appreciate the benefit of having someone around who knows the limits of city government’s power.

One other wrinkle: the ranked-choice voting system Portland adopted for its mayoral elections. Fifteen candidates made the ballot back in 2011. If even half as many hopefuls run next year, that’s six or seven people who aren’t Brennan to choose from. Voters seeking an alternative to the incumbent would boost Leeman’s tally even if she’s their second or third choice.

Leeman famously opposed efforts to reinstitute a directly elected mayor in years past. But hey, if you can’t beat ’em, beat ’em.

Chris Busby

About Chris Busby

Chris Busby is editor and publisher of The Bollard, a monthly magazine about Portland. He writes a weekly column for the BDN.