Exit, stage left

What does the stunning upset of city councilor Katherine Triantafillou mean for progressive politics in Cambridge?

by Jason Gay

In politics, losing is never easy.

But losing's one thing when you're a fading pol in the twilight of your career, à la freshly deposed Boston city councilor Albert "Dapper" O'Neil.

It's another thing altogether if you're an up-and-coming pol like Cambridge's Katherine Triantafillou, who also got unceremoniously bounced from a council seat last week.

Dap, 79, knew the writing was on the wall. Triantafillou, 49, never saw it coming.

"It's surreal," she says. "I don't think it was an outcome that anyone anticipated."

It's two days after the election, and Triantafillou is sitting in her North Cambridge home. A fire crackles in the wood stove. Triantafillou, whose black hair is cropped just below her ears, is dressed in a thick wool sweater and a turtleneck. A pair of small dogs, a Chihuahua and a spaniel, bounce around playfully in the den.

The three-term councilor is in an affable but quiet mood. Shocked? Perhaps. Triantafillou admits that the first loss of her political career -- she finished 10th in the race for nine council seats -- has yet to register fully.

"We certainly felt confident going into the election," says Triantafillou. "It wasn't like we weren't working hard."

Triantafillou's loss was a jolt to progressives throughout Cambridge. Many residents viewed her as the queen of the city's substantial left-leaning population. She was mentioned as a candidate for mayor, even for Congress. She wasn't supposed to go out like this, so fast, so soon.

Since the news of the upset broke, there have been dozens of calls, Triantafillou says. People calling to say they're shocked. People calling to say they're sorry. People calling to ask what's going to happen to the issues Triantafillou stood up for. People calling to get her to run again. Some people call up and just sob.

"It's been quite touching," she says.

Of course, the losing hurts Triantafillou personally, too. But she's not about to stick her head in a hole. This is not a burial, she says. She lost an election.

"I have my life," Triantafillou says. "This is a defeat, but I have a life. I don't think this is a defeat of me."

---

Triantafillou burst onto Cambridge's political scene almost as unexpectedly as she now exits. She won a seat on the city council in 1993 -- her first try for public office. It was a victory that surprised even her.

"I didn't expect to win, and I was shocked," Triantafillou recalls. "It totally interrupted my life."

Triantafillou's upset win infused new life into the Cambridge Civic Association (CCA) -- the city's old, occasionally stodgy liberal political organization -- which endorsed her candidacy. It also signified the power of the gay and lesbian vote; she and her partner, Joyce Kauffman, also an attorney, had long been active in local gay and lesbian legal work and politics, and Triantafillou aggressively courted and organized the city's gay voters.

"Katherine's election in 1993 was inspirational to our community in Cambridge," recalls Sue Hyde, a leader in the Lavender Alliance, the city's gay and lesbian political organization. "Prior to running for the council, she had been a leader on many projects related to gay and lesbian people. When she took her place at the council table, many of us knew that we not only had a friend at the table, we also had someone whose own personal political history was synchronous with ours."

But Triantafillou was not just the "gay and lesbian councilor." Over time, she significantly broadened her constituent base, not only in her North Cambridge neighborhood, but also around the city. She became known as a strong advocate for women and women's safety issues, and, with the backing of council colleague Kenneth Reeves, she developed strong ties to Cambridge's minority neighborhoods. "She was a white woman who understood a lot about the oppression of all kinds of people," Reeves says bluntly.

Triantafillou also never turned her back on the political insurgents that Cambridge is full of. Most elected officials make it their business to stay as far away from them as possible, but ranting radicals didn't bother her a bit. If you had a beef with anyone from the local cops to the secret police in Latin America, she was your councilor.

She had her critics, of course. At times, Triantafillou was seen as too pushy, too aggressive, too divisive, too sharp-tongued. She despised the city's old-boy political network and made no bones about it. She openly sparred with council colleagues. She never hid her distaste for Cambridge's long-time city manager, Robert Healy, who was at the center of several discrimination disputes involving city employees.

Triantafillou's bull-in-a-china-shop approach didn't just irritate her opponents. Her style also irked her more moderate colleagues in the CCA, who viewed her City Hall clashes as detrimental to the organization's team spirit. When Triantafillou won re-election in 1997, placing third out of 19 candidates, and announced that she wanted to be mayor (in Cambridge, the council elects the mayor from its membership), CCA leaders were miffed that she said so before the organization collectively decided who would be its nominee. "We were rather taken off balance by Katherine going public with her interest," the CCA's then-president, Geneva Malenfant, said at the time.

Triantafillou's mayoral maneuver blew up in her face. Going into the city-council vote, she thought she had the CCA's backing, and had also secured the unattached Reeves for a critical swing vote. But in a last-minute switch, her CCA colleagues backed long-time CCAer Frank Duehay instead, pushing Triantafillou's bid aside. No matter whether you thought the CCA's move was sleazy or simply a hard-nosed power play, Triantafillou was clearly embarrassed. Furious, she quit the organization soon after.

Ditching the CCA seemed to energize Triantafillou's career. Unattached and uninhibited, she was free to do and say whatever she wanted. She continued to wage war on the old-boy network, and she became involved in issues such as local health care and affordable housing. She pursued a master's degree in public policy at Harvard's Kennedy School of Government. Recently, she orchestrated a sweeping anti-asbestos ordinance that won the support of every one of her fellow councilors, including former CCA colleague Kathy Born. "That was really her finest moment," Born says.

Triantafillou's political future felt so secure that she dissolved her law practice in order to concentrate on her career in public office. She made little secret of her intention to run for mayor again, in January 2000. She was even mentioned as a possible dark-horse challenger to Mike Capuano for the Eighth Congressional District seat.

And then came November 2.

---

Of all the possible scenarios conjured up by Cambridge political junkies going into last week's election, Triantafillou's losing was not one of them. Most people thought that all seven incumbents were going to win, with two newcomers taking the seats vacated by the departing Duehay and Sheila Russell. If another incumbent got bounced, it was generally agreed it was going to be Reeves or Henrietta Davis, a CCA councilor who finished ninth in 1997.

"I'm stunned by Triantafillou's demise," says Glenn Koocher, who hosts a cable-television show on Cambridge politics.

Koocher speculates that Triantafillou lost because her battles in City Hall had alienated some of her constituents. This may be partially true -- but only partially. A far more compelling explanation is that Triantafillou was the unlikely victim of a progressive overload. The '99 race was flush with lefties, including two impressive newcomers, 27-year-old wunderkind Marjorie Decker and former Tax Equity Alliance for Massachusetts head Jim Braude. What's more, two progressive incumbents, Davis and Reeves, were perceived to be in trouble.

As a result, Triantafillou found herself fighting for attention. This was significant, since Cambridge's proportional-representation (PR) system asks voters to rank the candidates -- number one for their first choice, number two for their second, and so on. Given the options and the perception that Triantafillou's seat was safe, many progressive voters chose to spend their top votes elsewhere. This cost Triantafillou dearly.

"People tried to outsmart the PR system," Triantafillou says. "A lot of my votes went to Marjorie Decker. A lot of my votes went to Jim Braude."

Triantafillou made mistakes too, of course. As solid as her '99 effort seemed to be, her campaign should have noted the flood of talented candidates and been more on the watch for voter defections. And though there had been talk early on about a new progressive slate to challenge the CCA, it never materialized, leaving Triantafillou without the kind of organizational backing she enjoyed in 1993, 1995, and 1997.

Whatever caused her downfall, progressive Cambridge woke up the morning of November 3 with a hangover and a big fat guilty conscience.

"Not only does the community lose, but we [progressives] lose a really important voice," says Decker, who acknowledges that her own celebration has been "tempered" by Triantafillou's loss. "I was looking forward to having her as a mentor."

---

It's unclear what impact Triantafillou's loss will have on Cambridge politics. Certainly, her council experience will be missed. It will be tough to replicate her work on issues such as health care and affordable housing, and her advocacy for constituencies like the city's gay and lesbian residents. No doubt some councilors are thrilled that she's gone, but others will miss Triantafillou's passion and drive. "To me, her loss is quite irreparable," says Ken Reeves. "Katherine has been an extraordinary ally."

But Triantafillou's defeat is far from a death blow for progressives. Some of the slack will likely be taken up by Decker and by Braude, who is expected to press the city to drop its weak-mayor/city-manager system in favor of a mayor elected by popular vote. (One irony of Triantafillou's fall is that if she had managed to get on the council with Braude and Decker, she would have been in an excellent position to become the city's next mayor.)

Triantafillou is on vacation now, someplace south, someplace warm. The trip was originally planned as a break before getting back to council business. It is something else now. The councilor isn't sure what's next. She could do some consulting. She could work in public policy. She could run again in 2001. It's all possible.

"I don't know what my plans are," Triantafillou says. "It's too fresh, too new. I was so totally focused on what I was going to do next week, and next month."

She'll be back in Cambridge soon, to finish out her term, to pass the baton before she wanted to pass it. Beyond that, things are less clear. The only thing certain is that Katherine Triantafillou will miss being a city councilor.

"I truly loved the opportunity to do this," she says.

Jason Gay can be reached at jgay[a]phx.com.