Leeman’s Way
An exit interview with the former, and maybe future, Mayor of Portland

by Chris Busby

Nine years ago this month, in the first editorial published in The Bollard, I tried to put the kibosh on a scandalous rumor that I married Portland City Councilor Cheryl Leeman. The truth is that Leeman married me — that is, she officiated at my wedding, in July of 2005, to a woman who worked for another city councilor. (Portland is Maine’s biggest city, but entanglements like this prove it’s really a glorified small town.)

A third city councilor, Peter O’Donnell, claimed Leeman’s role as a notary during the ceremony was proof of a conflict of interest that should effectively end my career. “You shouldn’t be covering anybody on the Portland City Council, because you’ve shown that you have a personal connection with one other councilor,” he told me back then.

Much as I hate to admit it, O’Donnell was right — about the second part, anyway. During the first half of the previous decade, when I worked as a reporter for Casco Bay Weekly and, later, the Portland Forecaster, Leeman morphed into something more than a subject of, and source for, news. She became a friend.

We didn’t hang out at the bars downtown and get stoned like other city officials and I did, though Leeman once met me for beers at Howie’s Pub, the friendly tavern in the East Deering neighborhood she’s represented on the council for three decades. Ours was mostly a phone friendship. I’d call to get comment for some story and inevitably the conversation would drift off the record into what was really happening around town and in our lives — local gossip, the stories behind the story, front-porch talk.

When I told Leeman in the spring of 2005 that I was engaged, she was thrilled for me. And being a local-news junkie, I could think of no one more appropriate to officiate at my wedding than Portland’s longest-serving city councilor and former, two-term, mayor. (She gladly accepted the job, but refused the $50 check I tried to give her for her notary service. As I wrote at the end of that first editorial, “I guess some politicians just can’t be bought.”)

Earlier this summer, when Leeman announced she will not seek reelection this fall, she asked if I would write a story about her time in city government, “as who knows me better than you do”? I replied that I’d be honored, though as this backstory implies, I may not be an entirely impartial observer of her career.

As we buckle down for the blitzkrieg of bullshit brought on by another election season, let’s brace ourselves with this tale of a politician who tells it like it is and embodies the spirit of public service — actually serving the public, working with others to solve problems, helping people get the government they pay for and deserve.

Leeman’s been pulling double-duty in this regard for much of her professional life. In addition to her service on the city council and scores of municipal boards, committees and task forces, Leeman worked for 18 years as a local representative for Sen. Olympia Snowe, handling constituent issues from Snowe’s home office in Portland.

“It was an awesome job,” Leeman told me in the fall of 2012, as she was preparing to leave that position in the wake of Snowe’s decision to leave the Senate. “It’s not often you can say you loved going to work everyday.”

Leeman said her most treasured memory of that job was the time she helped a Gulf War veteran suffering from ALS (Lou Gehrig’s Disease) get the military benefits he and his family were being denied due to bureaucratic hang-ups in Washington. The soldier died shortly after the matter was settled, but did so “knowing his family would be taken care of,” Leeman said.

Leeman also fondly recalled the friendship she developed with a Peace Action Maine activist, Sally Breen, who’d share baked goods with the senator’s staff when her group held sit-ins at Snowe’s office. “She made the best brownies ever,” Leeman declared.

This kind of “brownie diplomacy” is typical of Leeman’s personal approach to government and disregard for party politics. Her distaste for partisanship is one reason why, unlike so many of her council colleagues over the years, she’s never run for higher office. “There’s no way that I could be myself, and be true to my values and be principled, if I had to join one side or the other if I thought [that side] was wrong,” she told me last month while we chatted at her dining room table.

Of course, being a registered Republican in a city packed with Democrats could be another reason, though Leeman downplays her membership in the Elephant Party, insisting she’s an independent at heart.

“Call me a Republican if you want, but nah,” she said. “There are those that love painting me in that corner, but … don’t bother, because I don’t belong in that corner, and if you look at my [city council] record, it was never based on my being a Republican.” After all, she notes, “I live in a heavily Democratic area,” and those voters have elected her by wide margins nearly every time she’s run.

Leeman has long been the only Republican on the (officially nonpartisan) nine-member council that Democrats have dominated for decades. And she’s not infrequently been the sole vote opposing decisions by the other eight. But she attributes that to her principles, not her politics.

“A lot of it goes back to the way I was brought up,” she said. Leeman’s father, a veteran of World War II and the Korean War, was the patriarch of a traditional family in Scarborough. He worked for the military and for General Electric while Leeman’s mother stayed home to raise the kids.

“My father always taught us there’s either a right way or a wrong way. So all of us were brought up under the umbrella of being very principled,” Leeman recalled. “Sometimes it’s too easy to go along, and you feel the pressure. The pressure is intense when you’ve got eight other people who’d say, ‘What the hell?’ and put their hand in the air. But if it’s not the right thing, I can’t do it. That’s just who I am.”

Case in point: In early 2003, the Portland City Council joined the governing bodies of nearly 50 other cities by passing a resolution opposing the imminent invasion of Iraq. Leeman cast the lone vote against the non-binding resolution, but not because she disagreed with the ideas it expressed (she said she agreed with many of them). Rather, she does not believe municipal officials should weigh in on matters of U.S. foreign policy as though they are speaking for the entire city. “Some in the audience heckled her,” the Portland Press Herald reported.

In June of 2002, during another emotionally charged council meeting, Leeman was the lone vote opposed to requiring organizations that get grant money from the city to offer health insurance coverage to their employees’ domestic partners (in those cases where the organization offered married workers those benefits). The Salvation Army and other religiously affiliated groups with city contracts sought the same exemption from this part of Portland’s domestic-partnership ordinance. Leeman, who supported the ordinance itself, also supported the godly groups’ prerogative to discriminate in this regard, arguing that allowing them to do so was akin to honoring a “diversity” of views. Rejecting the Salvation Army’s request for an exemption, as the council ultimately did, “is the greatest example of hypocrisy that I’ve ever seen,” she said at the time.

Stances and statements like that are what raised the blood pressure of fellow councilors like O’Donnell, the city’s first openly gay mayor. And though Leeman was firmly stuck in the council’s conservative minority, O’Donnell may have had cause to be paranoid about her influence. In a 2001 profile for Casco Bay Weekly, Al Diamon wrote of her “relentless efforts to recruit Republican candidates to run for the council.”

Leeman denies she tried to recruit fellow Republicans, but even if she did, those efforts had very limited success. She was more influential when her arguments convinced conservative, off-peninsula Democrats to vote with her, which happened fairly often. And when Green Independents gained a foothold on the council in the second half of the ’00s, Leeman’s stock rose considerably.

Most famously, in 2007, Leeman joined three Greens and maverick Democrat Ed Suslovic to support The Olympia Companies’ proposal for redevelopment of the Maine State Pier over the competing plan submitted by Ocean Properties — a politically connected company that enlisted former Democratic Sen. George Mitchell; Democratic Gov. John Baldacci’s brother, Bob; and (who else?) O’Donnell to pitch its $100 million project. (In the end, both developers bowed out.)

So now that Leeman’s leaving, the Democrats in charge, like Mayor Mike Brennan, can breathe easy, right? Not exactly.

Since she announced her political retirement earlier this summer, Leeman said people have approached her “every day” urging her to run for mayor next year. Before the position of a directly elected mayor was approved four years ago, Leeman was one of the idea’s staunchest opponents — citing, among other points, the position’s potential to over-politicize city government.

When I asked Leeman last month if she’ll run, she didn’t say yes. But neither did she say no. Given her history of stepping up to the plate every time she’s asked, that means she very well may.

 

Street lanes and lawn signs

In the early 1980s, Leeman was a stay-at-home mom running a daycare out of her home in East Deering — the same house she lives in today. She’d quit a corporate management job to start the daycare, in part because the other child-care options around weren’t up to her standards, and because “that’s the only way I could financially stay at home.”

One day, a neighbor who lived a block away, on Washington Avenue, called Leeman to ask if she knew why city workers were painting dots down the middle of the street. “Uh, no,” Leeman replied. “Why would I know that? Call Public Works,” she said. So the neighbor did.

The city’s response: Washington Avenue is too wide, so we’re making it a four-lane byway.

The neighbors’ response: no way. “This is a highly residential neighborhood. We can’t let that happen,” said Leeman, recalling the resolve of the small group of daycare, PTO and tee-ball parents who began meeting around her dining room table to plot a way to thwart the traffic plan.

Leeman contacted a state legislator, who sent her an official-looking book of traffic codes and a request: “‘Don’t tell anyone where you got this from.’” The parents decided that offering the city an alternative plan would be a better strategy than simply being “naysayers and NIMBYs,” as Leeman put it. So they did their homework, bought poster board and markers, and made their own traffic diagrams, showing how turning lanes could alleviate the problems. Over 200 people from the neighborhood showed up for the public hearing at City Hall, and the news media followed.

City officials, with what Leeman called their “fancy flip charts,” were caught off guard. The councilor representing East Deering in those days ducked out of the hearing and called then-city manager A.J. Wilson. Wilson “comes running over in the middle of this meeting and he tries to convince us that there’s no difference between what we’re proposing and what the city’s proposing,” Leeman recalled.

“We looked at this guy and we said, ‘Do you think we’re stupid? Of course there’s a difference. We’re not buying that.’” Faced with the sizeable crowd and all the TV news cameras, Wilson’s side “backed down very quickly,” said Leeman. “We walked away saying, ‘Wow, you can beat City Hall! That was awesome.’”

But not long after the Battle of Washington Avenue was won, a new fight emerged. The school board revealed plans to close Presumpscot Elementary, in East Deering, and bus its students to schools in two other neighborhoods. The parents reconvened in Leeman’s dining room and did their own analysis of city population trends, which showed that development in North Deering would cause overcrowding in that neighborhood’s school if East Deering’s kids were sent there.

“We all came from business,” Leeman said of the dining-room cabal. “When you’re in business, you identify the problem, you identify the solution. [In] politics, you kind of go around the barn and you process it to death first, but more often than not you come up with the same conclusion.”

Sure enough, the school was spared by a 5-4 vote of the board.

“That’s when we all said, ‘We need to get on the other side of the podium, to protect our interests,’” said Leeman. “And they all looked at me. I said, ‘I can’t speak in front of a camera. Are you kidding?’ But then I said, ‘If you all will support me, I’ve never run a campaign, but we can do this.’”

Leeman said her first run for the school board was “the purest form of grassroots campaigning.” Neighbors called other neighbors. A fireman from the neighborhood cut a stencil for Leeman’s spray-painted signs and the owner of the neighborhood market paid for 75 of them. Supporters held bake sales, spaghetti dinners and a dance to raise more money, and Leeman knocked on doors every day.

She lost by 35 votes. But worse than that, the incoming school board member used a procedural maneuver to reverse the 5-4 vote that had saved Presumpscot School.

That move upset a lot of people, not least of all Leeman, who vowed to run again. And this time she won.

Leeman soon made a name for herself on the school board through hard work and a novel idea: a public-access television show, called Inside the Portland Public Schools, that highlighted school programs, teachers and students. “I felt like people didn’t know enough about the school system, and the best way to get parents and people engaged is to put their kids on TV,” she said. “And it worked! Everybody was watching: grampas, uncles — ‘Oh look, Susie’s gonna be on next week!’ Huge hit.”

Leeman quickly learned how local government and politics really worked. For example, city council and school board races in Portland aren’t actually nonpartisan at all.

At the end of her first three-year term on the school board, Leeman wanted to run for the city council seat representing her neighborhood’s district, District 4. A fellow school board member active in the Democratic Party told her: “It’s not your turn, and if you wait we’ll support you later on,” Leeman recalled.

Unbeknownst to that school board member — and pretty much everyone else at the time — Leeman was enrolled in the Republican Party. But she was more offended by the notion that local party bosses of either persuasion determined who ran for office. “It wasn’t supposed to work that way,” she said. “This is a democracy we live in …. I said, ‘Sorry, I’m running and I’m in it to win. See you at the finish line.’”

Leeman set out to run what she called “a class campaign,” by which she means a classy campaign. For example, rather than spray-paint the stenciled signs, which made the paint run and look messy, she and her husband spent many nights in their basement hand-painting them to letter-perfection. She chose a maroon color and put her name on an upward slant, “just trying to do something a little bit different.”

Her opponent, fellow school board member Jim Banks, had a hard time at the doors in East Deering. “They basically shunned him and said, ‘This is Leeman territory. Don’t bother,’” she said. “He couldn’t even get a lawn sign in this area. Not one. But he took all of mine one night in a truck,” she recalled with a laugh. “We never did find ’em.”

The Dems backing Banks “knew that I didn’t have a lot of money, and every one of those signs were a couple bucks, plus the stakes,” said Leeman. “So that pissed people off.”

“I don’t do that stuff,” she continued. “I don’t have to. I’m a strategist.”

Leeman won that city council race. It was the spring of 1984.

 

Battling the Old Boys

Leeman arrived on the council at a critical time in Portland’s development. “There was a recognition within the public that Portland, back in the ’80s, was not a very attractive place, and that we needed to get some things done,” she said. “The Old Port wasn’t safe, Congress Plaza was drugs and prostitution, and yet it was a remarkable city. Those of us who had vision could see that there was so much potential, but the folks that were in power at the time weren’t always visionary.”

The male Democrats who controlled local government began to be challenged by women, of all political persuasions, who saw what Portland could become. “It started one by one, one seat at a time, and we started to see the makeup of the council change,” Leeman said. Pam Plumb and Linda Abromson had recently won seats and been appointed to serve year-long terms as the city’s (largely ceremonial) mayor — in ’81 and ’82, respectively. Then Leeman arrived, followed by Ester Clenott, and both also served as mayor — Leeman in ’88, Clenott in ’89.

“You saw a shift,” said Leeman, but the old boys “had five votes locked up, so quite often there actually were votes right along gender lines — five men, four women.”

“Some of it was a power struggle,” she continued. “There were some significant five-four votes that were taken that benefited friends of theirs, certain developments, things that we all knew were wrong, but we only had four votes.”

The old-boys network used to “hand-pick” candidates for the planning board who could be trusted to play along. “I wouldn’t call it ‘corruption,’” Leeman said. “It was one hand washing the other. It was that kind of politics.” Leeman and her allies on the council put a stop to that practice, instituting a formal interview process for prospective members of city boards and, in one case, refusing to reappoint a planning board member loyal to the old guard.

“They thought they could embarrass us publicly and force us to vote for him, and we said, ‘Sorry,’ and it didn’t happen,” Leeman recalled. “This poor guy, he’s standing up there, and I thought, ‘Well, you asked for it.’ … It was embarrassing, but it sent a clear message that we’re done — done, a new day.”

When Leeman became mayor, one of the first things she did was reform the council’s work habits. “The absolute biggest thing was these midnight, one o’clock, two o’clock meetings,” she said. “We’d have budget meetings and [the old guard] would all go have drinks in between the afternoon and evening meetings. And we’re going, ‘This isn’t the way you conduct business here in the city.’”

Mayor Leeman instituted a new rule: “I said, ‘If we have not finished the agenda by 10 o’clock, as chairman and the mayor I will make a decision on what items we will work on and the rest will come back the following Wednesday.’ They laughed. They said, ‘Yeah, right.’ It only had to happen once. I called ’em all back the following Wednesday — never happened again. You’d be surprised how much business got done between 9 and 10.”

 

A third term as mayor?

While these sorts of inter-council tussles continued into the ’90s, Leeman continued to defend her home turf in East Deering. In his 2001 CBW profile, Diamon notes a number of battles she won in those days: nixing a halfway house for nonviolent offenders in 1993, killing plans for construction of a state Department of Human Services office building in a residential area in ’97 — the same year Leeman beat back an attempt to bring back the directly elected–mayor position.

Leeman’s staunch defense of her ’hood made her unbeatable in District 4 — she ran unopposed several times — but that same record could be a liability if she decides to run for mayor next year. A neighborhood activist on the peninsula told me she’d never vote for Leeman because the councilor’s concern about social-service programs in residential areas doesn’t seem to apply to those introduced into neighborhoods closer to downtown.

What changes would Leeman advocate if she were the boss of Portland?

For one thing, there’s be fewer tax breaks for developers and special tax-increment-financing (TIF) districts around town. Given the sorry state Portland was in when she was first elected to the council, and the explosion of development that’s taken place since, there’s no good reason why property taxes haven’t gone down, rather than way up, over this period. But the city has routinely handed out big tax breaks to stimulate development and diverted property tax revenue from TIF districts into special accounts for purposes other than running the city. Leeman would change that if she could.

She’d also cut way back on the city’s borrowing. In the past couple years, the council has far exceeded the $10 million annual cap it imposed on itself for bonds to finance big capital projects. Having seen several boom-and-bust cycles during her tenure, Leeman knows hard times will come again, and thinks the city should be more cautious.

Aggravations associated with Portland’s permitting process have been a perennial complaint among homeowners and entrepreneurs. Leeman said that although some improvements have been made of late — the system recently joined the digital age — it’s still much too frustrating to do business with City Hall. She likes the idea of a new rule whereby if an applicant doesn’t get a response from the city within two or three days for, say, a permit to build a porch, that permit is automatically granted.

Policies aside, Leeman’s strongest political asset, should she run for the citywide office, is her own story. It’s the story of a divorced mother of two who became the longest-serving city councilor in modern Portland history. It’s the story of how, during her second term as mayor, from 2000 to 2001, she shepherded city government through the turmoil caused by the unexpected passing of City Manager Bob Ganley, and again in the aftermath of the 9/11 attacks — which, lest we forget, partly originated here. It’s the story of how Leeman, who’s now in her mid-60s, faced down breast cancer in 2007, undergoing a double mastectomy to beat the Reaper and then using her experience to help other women deal with the disease.

“I had somebody say to me the other day, ‘Oh, you’re so politically astute,’” Leeman told me as our conversation at the old dining room table wrapped up. “And I said, ‘Not really.’ I’m kind of misunderstood.

“I guess I could be more politically savvy than I had been — you have to learn something along the way,” she continued. “But I never tell a lie, so I never get caught up in a lie. And I’m a straight shooter, and I call ’em like I see ’em. So if that’s being politically astute, I guess I am.”