What Money Can't Buy

Fresh off his May 15 primary victory, mayoral candidate Charlie Hales fired most of his staff last week. As a gesture of appreciation, Hales handed each an autographed photo of himself posing with the staffer he had just canned.

Meanwhile, Rep. Jefferson Smith, the surprise second-place finisher, says he wanted "healing" after a tough campaign. So his backers swarmed Twitter, Facebook and blogs to pitch for the support of the candidate whose hopes Smith had extinguished, Eileen Brady. 

Voters may be sick of the campaign just finished, but Smith and Hales are already working to win in the November general election. 

And no one has truly answered the question that Portlanders are still asking: How did Brady—a candidate who started with every advantage and spent a record $1.3 million in the primary—fail in such epic fashion?

Until the primary, former City Commissioner Jim Francesconi, who spent nearly $1 million in the 2004 mayoral primary, only to lose in the general election to a former police chief, Tom Potter, was the high-water mark for political folly.

The title now belongs to Brady. She won just 22 percent, spending a jaw-dropping $46 per vote—three times what her opponents spent per vote, and more than double Francesconi's historic $21.

Many of Brady's faults overshadowed Hales' and Smith's own shortcomings, and with her gone, their weaknesses will stand in stark relief.

The way this race played out has provided lessons for Smith, Hales and future city candidates—but most important, lessons for voters as well.

Know Thyself.

There are struggles in running for office that can be daunting even for someone with a successful career, including establishing one's identity with voters. Brady sought to define herself as the sustainability candidate who could bring jobs to Portland. 

But Brady often contradicted herself. While draping herself in green, she flip-flopped on the proposed $3.5 billion Columbia River Crossing and adopted a "build, baby, build" approach to win business and labor support.

She was also unprepared for scrutiny. When her claim of being a co-founder of New Seasons Market came into question, Brady attacked the news media for questioning her; her son, Colin O'Brady, recently blogged that his mother was the target of an "unfair and editorialized sexist negative campaign." (Brady didn't return WW's calls.)

When WW reported that a police officer had excluded her from Tom McCall Waterfront Park in 2003—and noted her threat to call "friends" at City Hall to help her get out of the ticket—she responded by calling the cop a liar. When her answers ran long during KATU's debate, Brady on live TV complained that the floor director (who stood in plain view) was making it difficult for her to see when her time was up.

By contrast, Smith and Hales took their knocks in stride. Smith dealt with public exposure of his attention-deficit disorder, spoke frankly of the medication he takes to manage it, and acknowledged a history of managerial mishaps without getting defensive. 

Hales faced revelations that he'd avoided Oregon taxes as a Washington resident while continuing to vote here—and at first didn't tell the truth about it. But he apologized (sort of) and addressed the issue directly (if incompletely) at campaign events.

They also showed they knew who they were and weren't afraid to run on that image. When Smith entered the mayoral race last September, he was five months late to the party and, because of an injury, wore a patch over one eye. The two-term state lawmaker—ostensibly the "Keep Portland Weird" candidate—promised to run a "fun" campaign. He cracked jokes, turned cartwheels in the street and tweeted madly.

As a former city commissioner, Charlie Hales also had an identity: He'd championed the streetcar, knew City Hall and promised steady (if slightly dull) leadership as mayor, not unlike the campaign he ran. Hales' persona was as gray as his hair.

"I'm pretty comfortable in my own skin," Hales says. "I also, unlike others in politics, have an actual life to go back to if voters disagree. This gives me an even greater freedom to be myself than someone who might be desperate for the next office."

Know Thy Audience.

Brady oftentimes left events having won more votes for her opponents than for herself.

She was the guest of honor at a dinner hosted last summer by two of Portland's busiest networkers, Stimson Lumber CEO Andrew Miller, the city's largest political contributor, and divorce lawyer Jody Stahancyk.

Neither Miller nor Stahancyk would comment on the 20-person gathering, but others who attended describe the evening as a debacle for Brady. Stephen Houze, a leading criminal defense lawyer, and other guests pushed Brady without success to describe the rationale for her candidacy.

Such scenes repeated throughout the campaign. In private meetings, Brady (and her advisers) told people she would be mayor and they needed to start dealing with her.

Smith and Hales, with more campaign experience, learned long ago to listen and respond. Hales stuck to the script he knew from experience that voters wanted to hear: He would return basics to City Hall. Smith knew his audience as well—progressive Portland. He'd oppose the CRC and fight for equity.

Going forward, however, both may encounter tension as they try to serve competing interests—a challenge a mayor must face. While folksy, Hales' campaign took in more than $200,000 from development and real-estate interests, and spoke of giving breaks in fees worth millions to business.

Smith has to reconcile his divided image as both the Occupy Portland candidate (as The American Prospect called him) and the choice of the Portland Police Association (which endorsed him and kicked in $10,000). 

Know Thy Opponent.

Hales—traditionally the proverbial tortoise in his campaigns—changed his message to fit the new circumstances, but the recalibration was subtle. Smith jumped in after Adams was out.

Brady never found a way to rebut Hales' "experience" claim. Nor did she take Smith seriously—until it was too late.

"What she was saying behind closed doors in terms of how real our candidacy was, I don't know," Smith says. "But it was not Eileen but Charlie who told me I didn't have a chance."

Smith and Hales are already trying to define each other. Hales is calling for more results and less rhetoric—a jab at his opponent, as Smith talks about an era of new ideas—a poke at Hales' being a retread.

Watch Thy Cash.

In his winning campaign, Hales spent $798,000. Brady burned through nearly that much cash by April and hadn't yet bought a TV ad. Her campaign had big overhead costs, as if it were a stimulus package for political consultants, yet ignored basic media strategy, including cable TV and direct mail. She finished deeply in debt after loaning herself $250,000.

Hales ended up loaning himself $100,000 while taking another $25,000 loan from a contributor. 

Smith's campaign hoarded its limited cash, making DIY ads out of footage recycled from campaign events. "I'm somewhat proud of being the only candidate to not go six figures into debt," Smith says.

But Smith and Hales handled their early money well and kept pace with Brady in the most important area: cash on hand. That's what buys TV time, and Brady's spending allowed them to overtake her. 

Know Thy City.

Portlanders see politics similarly to artisanal meats—they want to know how the sausage is made. They want a personal touch and know the difference between grass roots and AstroTurf.

Smith had a head start on his opponents in amassing and deploying an army of volunteers to canvass the city. His focus on the "ground game" was bolstered by the endorsement of key labor unions. Similarly, Hales, a veteran of old-school retail politics, says, "I was on the doors for months and months with no company."

Brady took a different tack. She branded herself the big-money candidate by telling The Oregonian in January she planned to raise $1 million for the primary. Her endorsement by the Portland Business Alliance, the city's most influential business group, only reinforced that image.

Brady's advisers persuaded her to run for mayor as if she were running for the U.S. Senate, saturating the broadcast media with ads. In contrast, Hales and Smith counted hundreds of volunteers spread out across the city. Brady's couldn't fill a bus.

It all ended in a sad scene on the afternoon of Election Day. Brady sat at a table in Pioneer Courthouse Square for "office hours." Two supporters held a banner behind her, and a third aimed a campaign video camera on Brady, who waited for voters to approach.

At first no one did, so Brady invited passersby to stop. Many had already voted. Others just weren't interested.

Brady found a woman to stop and speak with her, and the candidate looked hopeful.

They talked for a long time, before the woman told Brady she wasn't registered to vote. 

Staff writer Aaron Mesh contributed reporting to this story.

WWeek 2015