The Pioneers of City Hall

Lewis & Clark alumni play strategic roles in the fast-paced Portland mayor’s office.

Lewis & Clark alumni play strategic roles in the fast-paced Portland mayor’s office.

From left: Director of Strategic Initiatives Josh Alpert, Policy Director Jillian Detweiler, Mayor Charlie Hales, Chief of Staff Gail Shibley, and Communications Director Dana Haynes From left: Director of Strategic Initiatives Josh Alpert, Policy Director Jillian Detweiler, Mayor Charlie Hales, Chief of Staff Gail Shibley, and Communications Director Dana Haynes

Portland Mayor Charlie Hales takes pride in his Pioneer connections—after all, he took graduate classes in public administration at Lewis & Clark prior to winning election as a city commissioner back in 1992. (He also made the acquaintance of his wife-to-be, Nancy Sourek MA ’99 when they were both students on campus, but that’s a different story.)

Twenty years later, Hales was elected mayor in a landslide, pledging to restore public confidence in city government. And when it came time to choose the team he would take to City Hall, he discovered an excellent source of talent among graduates of Lewis & Clark. A third of his small, tight-knit staff are alumni: Chief of Staff Gail Shibley, Communications Director Dana Haynes, Director of Strategic Initiatives Josh Alpert, and Policy Director Jillian Detweiler. “We hire people who can think about the big picture and get things done—people who are well rounded and well grounded,” Hales says. “Lewis & Clark certainly deserves some of the credit for that.”

The Pio presence in City Hall isn’t happenstance. Lewis & Clark is highly regarded for academic programs in areas such as political science and environmental law. Just as important, the college is known for its ethos of public service that cuts across its three schools and academic departments.

We hire people who can think about the big picture and get things done—people who are well rounded and well grounded.Mayor Charlie Hales

His “gang of four,” as Hales jokingly calls his Lewis & Clark–connected aides, “have a really wide range of experience,” he notes. And that is a good thing.

Indeed, their personal backgrounds are as varied as the paths they took to City Hall. Shibley is a powerhouse policy maker with experience at the city, state, and federal levels. Haynes is a former journalist and accomplished novelist. Alpert has been involved in policy and politics since he was a teenager campaigning door-to-door. Detweiler made a visible mark on Portland working on real estate and transportation development for two decades before joining the mayor’s staff.

The traits these four disparate individuals share, Hales says, are a sense of humor to deal with “the absurdity in politics,” a talent for collaboration and negotiation in the “realpolitik” of city government, and a dedication to “working toward the common good.”

“The word that captures their spirit best is ‘communitarian,’” Hales says. “By the way,” he adds, “that’s a word I learned at Lewis & Clark.”

Gail Shibley JD ’09

Chief of Staff

Gail Shibley had already built an impressive resume in government before deciding in 2006 to pursue a law degree at Lewis & Clark. Despite her packed workdays as a top administrator for Oregon’s Public Health Division, she enrolled in the law school’s evening program. “It was one of those things I was always going to do but never seemed to have the time,” she says. “I reached a point where I realized that if I was ever going to law school it had to be now.”

Although she has not worked as an attorney, Shibley says her legal education has sharpened her approach to public policy—especially in her current job. As Hales’ chief of staff, Shibley’s task is to bring order and discipline to the ever-shifting landscape of City Hall. As the mayor’s hard-driving right hand, she works behind the scenes to keep his agenda on course. Hales keeps the big picture in mind; Shibley minds the details, making sure all the puzzle pieces fit together.

“I use my legal training all the time—administrative law, constitutional issues, you name it,” she says. “I’m not going to start writing wills or doing divorces, but one of the great things about a law degree is you can use it in lots of ways.”

When Mayor-elect Hales tapped Shibley to be his chief of staff, the move surprised many political insiders because she had never been part of Hales’ inner circle. But the mayor wanted a tough, independent thinker for the job, and Shibley fit the bill.

An Oregon native, Shibley had politics in her blood at an early age, volunteering while still in elementary school for Robert Kennedy’s ill-fated presidential campaign in 1968. She was in her early 30s when she served as a state representative in the Oregon Legislature. She received notice for being the first openly gay member of the legislature and impressed many as a savvy, energetic lawmaker with a promising future. After three terms in Salem, she lost a tight race for a city commissioner’s seat in 1996.

Deciding to take a break from Oregon, she moved to various government jobs in Germany and Washington, D.C., including stints working for the Federal Highway Administration and the U.S. Secretary of Labor. She returned home to Oregon to be an advisor to Gov. Ted Kulongoski’s re-election campaign in 2002 and went on to the Public Health Division. She was in that post when she enrolled in the law school in 2006, finishing the four-year evening program, she notes, a semester early.

Shibley has a hard time pinpointing the accomplishment she’s most proud of during her two years as chief of staff, undoubtedly because she is involved in nearly everything that happens in City Hall. Pressed for an answer, she cites attracting the World Indoor Track and Field Championships to Portland in 2016 (she is an avid runner). After some more thought, however, the answer becomes clear: She is most proud of assembling the team that works for the mayor.

“We’ve got an absolutely terrific, top-drawer group here—including the non-Pioneers,” she says, adding the tactful qualifier. “We have some strong personalities, but we share a common mission. I love being part of a team that’s working toward the greater good.”

Dana Haynes BA ’87

Communications Director

As an undergraduate at Lewis & Clark, Dana Haynes spent as much time in the office of the Pioneer Log student newspaper as the classroom. That turned out to be a sensible strategy, however, given that he knew what he wanted to be: a newspaperman.

Earlier in his youth, Haynes dreamed of pursuing an acting career but realized he had to commit to either the stage or the newsroom. He picked the latter and has no regrets about the choice. “I’ve been super lucky,” he says. “I’ve had the opportunity to make a living writing.”

Following a two-decade career in newspapers, Haynes has moved from asking questions to fielding them as Mayor Hales’ communications director. He helps articulate the mayor’s positions on the issues of the day to the press and public. Whether he is delivering pithy sound bites in front of television cameras, ghostwriting speeches, or staying on top of social media trends, he is involved in every facet of the mayor’s agenda. And whenever some controversy erupts or protesters converge on City Hall, he is in the thick of the action.

An Idaho native, Haynes attended Clackamas Community College and worked as a janitor at a Datsun car dealership before transferring to Lewis & Clark. Haynes parlayed his college extracurricular experiences and political science degree into 20 years as a reporter and editor spanning daily and weekly newspapers around the state, from the Oregonian and Salem’s Statesman Journal to the West Linn Tidings and the Lake Oswego Review. “I liked being behind the scenes as major decisions were made,” he says.

While still an undergraduate, Haynes found some success as a novelist, eventually publishing several mysteries under the pseudonym Conrad Haynes. His debut was a whodunit, Bishop’s Gambit, Declined, set at “John Jacob Astor College,” a thinly disguised Lewis & Clark. He later spent 15 years writing diligently, waking up early every morning to scratch out rough drafts with pen and paper. He wrote six more novels but wound up with nothing more than a collection of rejection slips. “It was depressing as hell,” he says. “But I kept at it.”

Haynes returned to bookshelves with the publication of his novel Crashers in 2010—published under his own name this time. He followed up with a series of thrillers featuring his heroine Daria Gibron, “an Israeli ex-soldier, ex-spy and adrenaline junkie,” who battles spies, gangsters, terrorists, and assorted villains around the world. The most recent installment, Gun Metal Heart, was published by St. Martin’s Press in summer 2014. Publishers Weekly called the book “a high-voltage, high-body-count thrill ride.”

Haynes had moved on to a new day job as public affairs manager at Portland Community College when Shibley, an old friend, made him the first recruit to the mayor-elect’s staff. Now, as a former journalist working for the “other side,” he takes the perspective that talking to pesky reporters isn’t a necessary evil but an essential part of the democratic process. “I help things be better,” he says. “We’ve gotten a lot of good things done, and that is very satisfying.”

Josh Alpert JD ’99

Director of Strategic Initiatives

Josh Alpert “absolutely hated” law school the first time around.

After graduating from the University of Pennsylvania with a philosophy degree, he moved straight on to law school at Boston University, already planning a career in public policy. But it wasn’t what he wanted, and he dropped out after a year.

Feeling “burned out and restless,” the Pittsburgh native decided he was fed up with the East Coast and needed a change of setting. He moved across the country to start over in Portland, working in a mall and taking on temp jobs.

Eventually, he enrolled at Lewis & Clark Law School, where he found the perfect place to pursue his passion for politics. “The law school lends itself to activism.” he says. “You learn how the law can shape public policy.”

Alpert gets to do exactly that as Hales’ director of strategic initiatives. His official portfolio ranges from education and the arts to equity and human rights, but unofficially, he is responsible for tackling some of the toughest issues facing city government. He has been instrumental in developing a controversial proposal to establish a fund for fixing city streets, finding a new site for a downtown homeless encampment, and stepping into contentious contract negotiations to avert a strike by the city workers’ union.

The Oregonian called the influential Alpert a “jack-of-all-trades” on the mayor’s team, adding, “There’s a saying among Portland Mayor Charlie Hales’ employees: The oceans cover three-quarters of the Earth, and Josh Alpert covers the rest.” He doesn’t shy away from tackling tough issues, he says, because controversy means that people care passionately: “That usually means it’s an important issue.” His law school education helped prepare him, he says, “for being in the thick of the fire.”

Alpert traces his fascination with politics back to high school, when he volunteered for a candidate for U.S. Senate. “I went door-to-door,” he says. “I was just a kid, but I realized I had the opportunity to have an impact on someone’s vote—that was mind-boggling to me.”

“We are such an accessible city when it comes to policy—the community is very engaged. I feel lucky to be doing this work in Portland.Josh Alpert JD ’99

While at Lewis & Clark Law School, he also held a job as a lobbyist for M&R Strategic Services, a political consulting firm specializing in progressive nonprofits, representing clients ranging from Planned Parenthood to Basic Rights Oregon.

He soon landed the post of campaign manager for Charlie Hales’ successful city commission re-election campaign in 2000 and later became his transportation liaison. When Hales resigned two years later, Alpert took a shot at running for his boss’ open seat. For three months he knocked on doors across the city. “I didn’t win, but I had a blast,” he says. He moved for a time to California, then back to Oregon, where he worked for the Trust for Public Land.

Alpert also reconnected with Hales, advising his election campaign and joining his team after he was elected mayor. “We are such an accessible city when it comes to policy—the community is very engaged,” he says. “I feel lucky to be doing this work in Portland.”

Jillian Detweiler BA ’87

Policy Director

Jillian Detweiler recalls her visit to Lewis & Clark as a prospective student—a soggy, gray day just before Thanksgiving when the campus was virtually empty. The shy teenager poked her head into the Frank Manor House and came face-to-face with the admissions director, who welcomed her warmly and engaged her in conversation by a roaring fireplace. “He completely sold me,” Detweiler recalls. “I got the sense that Lewis & Clark was the sort of place where people would take an interest in you.”

Detweiler says she was “not prepared” for college—working harder than she ever had in high school, interacting with students with whom she seemed to have nothing in common. “I was overwhelmed,” she says. “The experience befuddled my world view.”

But she made it through. She credits her time at Lewis & Clark with toughening her skin and broadening her perspectives—qualities that prepared her well for her current career in the hurly-burly of city politics.

Detweiler serves as one of Mayor Hales’ four policy directors, the point person on housing and development. She works with stakeholders ranging from affordable housing advocates to big-money condo developers and has a hand in virtually every major project under way or under consideration in the city. These cover the waterfront (sometimes literally), including the revitalization of the Lents neighborhood in Southeast, the growth of the upscale Pearl District, and the redevelopment of Veterans Memorial Coliseum.

Every day, she says, she is “confronted with really difficult issues” —homelessness, gentrification, and the growing gap between the rich and poor in modern society.

While she may have had a rough start to college, Detweiler eventually got her bearings in the classroom and went on to forge lifelong friendships. She grew up, as she puts it, “enormously.” As a student she also worked as a reporter and managing editor at the Pioneer Log newspaper (alongside her future City Hall colleague Haynes) and majored in political science. “But really, I could have majored in anything,” she says. “The important things were the critical thinking and communication skills.”

An early mentor was the late Professor of Political Science Jack Crampton, whose style of teaching, she says, was all about “bringing out your independent thought, not just memorizing facts.” He was an unforgettable character who “raised the bar on intellectual curiosity.”

She worked as a writer and editor in Washington, D.C., before going on to study urban and regional planning at the University of North Carolina. Her graduate studies made her aware of Oregon’s leadership in land-use regulation, so she made her way back to Portland.

Detweiler joined Hales’ staff when he was a city commissioner in the 1990s, then worked for the TriMet public transit agency for a dozen years. She oversaw transportation-related real estate development and worked to expand MAX Light Rail service.

Detweiler jumped at the chance to work again with Hales when she took the policy director post last June, becoming the latest Pioneer to join the mayor’s office.

“This is an extraordinary opportunity to serve the city,” she says. “I get almost teary talking about it, but being in a job where you can make a difference is an incredible experience.”

Romel Hernandez is a freelance writer in Portland.