Mayor of 'Portlandia': the real-life fight

Things didn't go so well with Sam Adams after voters picked him 4 years ago. Now, 3 contenders are battling to emerge from a large primary pack of would-be mayors.
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Charlie Hales

Things didn't go so well with Sam Adams after voters picked him 4 years ago. Now, 3 contenders are battling to emerge from a large primary pack of would-be mayors.

Half a century ago, every four years meant Oregon’s May primary was testing time for presidential candidates — the national news media flocked to the state, clogged the bar at the Benson Hotel, and put Oregon on the political map. No one pays any mind to that now, to the benefit of local candidates who are no longer under the shadow of the White House.

Ballots are already in the mail for Oregon’s May 15 primary and a few legislative races and a Democratic contest for attorney general are drawing attention. But the best contest is in Portland, with three well-matched candidates for mayor.

Unless one wins 50 percent in the primary (highly unlikely) the top two contenders for mayor of Portland move to November. In addition to the three leading candidates, there are 20 others on the ballot; none are expected to draw many votes.

The candidates make up a diverse trio: Charlie Hales, 57, is a former city councilman who spent the last 10 years in private business; Eileen Brady, 51, has strong connections with the city’s environmental, sustainability and organic-food communities; Jefferson Smith, 38, a two-term legislator from Southeast Portland, is best known for organizing young political activists.

The eventual winner succeeds Sam Adams, whose single term began amidst high hopes and much attention as the city’s first openly gay mayor, but crumbled after a series of bad personal judgments and misleading or false statements. For a city of two minds about its Portlandia image, a major question will be whether to roll the dice again on a promising young candidate or take a time-out to regroup.

All three candidates are Democrats in this deep-blue city and all have talked and walked iconic Portland issues, including public transit, sustainability, and diversity. The debate has been largely civil, with candidates perhaps holding some ammo for the fall election. Two closing debates produced as many yawns as cheers. “After months of joint appearances at forums across Portland, the candidates have sometimes acted like family members who have been on vacation together too long,” The Oregonian’s Beth Slovic said of the City Club debate, finding little real debating going on.

Most of the public campaigning in the past several days has been on The Oregonian's PolitiFact site, a fact-checking feature. With ballots already in the mail, and many returned, a political "twilight zone" in effect descends on the last two weeks of a campaign in Oregon.

In seven posts dated May 5, Hales got the most attention, with four checks on statements by or about the candidate. PolitiFact judged Hales's positions as "True" or "Mostly True" on statements about a systems-development charge, but "False" or "Mostly False" on statements about school funding and seeking a city contract. Smith gained a "False" rating for a water-treatment statement; Brady got a "True" on claiming co-ownership of a publishing group and a "False" on a water-treatment statement.

There are, however, differences that will need a Fall airing-out. Perhaps the most critical decision for Portland and the entire metro area right now is getting design agreement and funding for the Columbia River Crossing, the much-awaited third bridge linking Portland and Vancouver. Smith has strongly opposed present plans, Brady and Hales want changes but seem willing to move ahead. There are many players at the table from local, state, and federal agencies, but the mayor has one of the seats.

Portland has been on a heady run for a decade or more, attracting national attention for its lively downtown and success in attracting talented young people and others looking for a livable urban environment. But beyond Portlandia are a host of problems faced by all big cities: underfunded and struggling schools, gang problems, unemployment, and infrastructure.

Only Hales is experienced in City Hall, after 10 years as a city councilman, and that seemed enough as The Oregonian and Willamette Week, the city’s alternative paper, agreed in supporting Hales for his experience (WW also did an outstanding job of profiling the three candidates).

In its endorsement of Hales, experience was determinative to The Oregonian editorial board: "But right now Portland seems adrift, floating along with unacceptably high unemployment, letting streets go to potholes, watching businesses drift out of downtown. The times demand a strong, experienced and fully prepared mayor. That’s Charlie Hales.” Willamette Week explained its choice, “The fact is, when it comes to the substance of the mayor’s job, no one comes close to Hales. He’s ready to do the job, and do it well.”

The Hales campaign released results of a tracking survey April 24, showing him in a dead heat with Brady, 27 percent to 26 percent, respectively. Smith was at 16 percent, but 22 percent of the survey was undecided, with a high (4.5 percent) margin of error. Brady had a fundraising edge as of April 24, spending about $900,000 to $500,000 for Hales and $400,000 for Smith.

Brady drew early advantage as the first entry after Adams announced he would not seek re-election. She scooped up some early cash, endorsements, and was described by Willamette Week’s Corey Pein as “Portland’s most buzz-worthy politician in years.”

But some of the buzz had toned down and some of the core of Brady’s campaign had faded by the time ballots were mailed, including her major claim to fame, as a co-founder of New Seasons Market, a popular and trendy chain of local stores founded 13 years ago. As Pein and others have pointed out, although Brady’s husband, Brian Rohter, was a co-founder, Brady herself never had any role at New Seasons.

Brady in some ways is a Portlandia candidate; she was a college radical at Hampshire College in Amherst, Mass. and served jail time from a Pentagon protest in 1980. She turned her activism into more respectable pursuits at Evergreen State College in Olympia and got involved in the food-cooperative movement before moving to Portland with her then-husband and two children.

In Portland she alternated private-business and public-sector work, the latter with Ecotrust, the regional environmental and sustainability organization. She became a protégé of Stan Amy, whose Nature’s Fresh Northwest was a founding pillar of the region’s organic grocery industry. Amy and his wife have donated $20,000 to Brady’s campaign.

The knocks on Brady’s portrayal of her career have been part of what appears to be slippage from the “front-runner” status that many gave her as the campaign opened. More importantly, both Portland newspapers noted in their editorial endorsements that she has a somewhat fuzzy grasp of city issues. Willamette Week put it, “she is without a basic grasp of how city government works, filling in the gaps in her knowledge with jargon and buzzwords.”

Harsh words, but Brady’s lead in campaign fundraising may boost her into the November general election; some of that early “buzz” is still around and both editorial boards cited her energy and breadth of experience.

Somewhat like Brady’s identity with New Seasons, Jefferson Smith is joined at the rib with The Bus, an ambitious voter-recruiting effort he began in 2001 to help himself and other Democrats win local elections. Several refitted school buses were used to transport young people into competitive districts to rally support for candidates. The idea caught on, and has become somewhat of a political icon — and it’s all Smith.

Essentially The Bus is the heart of Smith’s rather thin political resume. And that is a problem as well as an asset.

I ran across Smith in 2008 at a reunion of people who had been involved in the 1970s in Demoforum, a freewheeling gathering of (mostly) young Democratic activists that produced a lot of future office-holders. At the reunion’s conclusion, party leaders trotted out half a dozen of their “new stars” for that year’s legislative campaigns. Smith was clearly one of the most impressive; a large, bumptious chap with the sunny disposition of his dad, longtime Democratic politician R.P. (Joe) Smith. Everyone thought young Smith had potential, but wondered how he would play in the Southeast Portland district where he had recently moved to run for office.

He played well, and has served two legislative terms to mixed reviews. There is a persistent concern among some that Smith’s eyes are already on higher office before he has paid his dues at home.

The tendency to keep an eye on larger goals while the house is burning down around you has raised questions about Smith in the media and even among friends. Smith graduated near the top of his class at Harvard Law, and got first-rate clerking assignments. But he bailed out of his first job at a top New York firm after a few months, and stayed very briefly at the Stoel Rives firm, Portland’s largest. Associates said he was so busy working to organize The Bus that he did little legal work. As director of The Bus, he ran a notoriously sloppy financial ship, and lack of attendance to details has caused him to pile up traffic tickets and had his law license suspended.

For a legislative role — such as his House seat — that might not be a problem. But Portland’s mayor-council form of government forces a mayor to actually run at least one major bureau (most previous mayor have selected public safety), and manage the budget. It is an executive position and Smith’s only executive experience is The Bus. At age 38, Smith is clearly a young man on the rise; both Portland editorial boards laud him for having new ideas and bringing spirit and energy to the race, but are not sure he’s ready to run the city. “He offers the promise of good things but also the potential to fail spectacularly,” Willamette Week concluded editorially.

Charlie Hales is the oldest of the trio, with experience in both public and private positions, although most has not been as a chief executive.

Hales was on the City Council from 1993 to 2002, when he abruptly resigned his seat to join a large transit company, HDR Inc., designer and builder of transit systems. He built on his Portland legacy, a downtown streetcar line running from busy Northwest Portland to Portland State University; it’s been a boon for riders and also a tourist draw. Much of the money for street-car systems in other cities such as St. Louis, Miami, and Minneapolis has come from a federal grant program championed by Congressman Earl Blumenauer, D-Ore, who worked with Hales on the plans while both were on the City Council.

Hales knows the city and its council politics and has a key endorsement from former Mayor Vera Katz, who remains a popular figure in the city. His City Hall experience figured hugely in endorsements by the two Portland newspapers. Noting Hales’ abandonment of his Council post in 2002, The Oregonian concluded, “Hales wasn't ready then to be the chief executive of this city. He is now ... Hales is seeking to return to public life as a wiser, more humble and more effective leader.”

The chief rap on Hales is that he is too flexible, perhaps too pragmatic. He began his public life lobbying for the fiercely conservative homebuilders’ association; he was a registered Republican. By 1992 he changed registration to non-affiliated (city offices are nonpartisan), and defeated a popular but fading incumbent. Councilman Hales voted on several issues against the interests of his former employers, and established a reputation for independence. He became a Democrat in 1998.

Hales also stands accused of moving across the Columbia River to Stevenson, Wash., between 2004 and 2009, where he filed residence for tax purposes — allowing him to escape Oregon income taxes — while at the same time keeping an Oregon residential address to vote in Oregon elections. Most of his work for HDR was outside Oregon, but using one state as a residence for taxation and another for voting is sensitive in Oregon; in a similar case in 2010 it damaged the campaign of Republican Chris Dudley, a candidate for governor.

If Hales’ tracking poll is correct, Jefferson Smith will be the odd man out on May 15, but Smith’s legendary energy and coterie of volunteers could surprise his more senior opponents. Otherwise a Hales-Brady general election will give Portland some contrasts in personality and life story if not serious divisions on issues facing Portland and most other big cities in a recession-weary and budget-short world.


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About the Authors & Contributors

Floyd McKay

Floyd McKay

Floyd J. McKay, professor of journalism emeritus at Western Washington University, was a print and broadcast journalist in Oregon for three decades.