Portland City Council, Position 2
Dan Ryan

Something is missing from the Portland City Council since City Commissioner Nick Fish's death in January from abdominal cancer.

It's not just a tie-breaking fifth vote that's gone. Fish's death deprived the city of both the council's longest-serving member and its peacemaker.

In an Aug. 11 runoff election—held at an unusual time because of Fish's sudden departure—voters will choose between two civic leaders seeking to serve the rest of Fish's term, which ends in 2023: former Multnomah County Commissioner Loretta Smith and Dan Ryan, the onetime executive director of All Hands Raised, an educational nonprofit.

Both candidates have been in civic life for decades: Smith, 55, as an aide to U.S. Sen. Ron Wyden (D-Ore.) for more than 20 years before she served as county commissioner from 2011 to 2019; Ryan, 58, as a senior executive at Portland State University and Oregon Ballet Theatre and a member of the Portland School Board before joining All Hands Raised.

Both contenders boast an impressive list of supporters: Smith has backing from Wyden, Oregon Labor Commissioner Val Hoyle, several labor unions, and longtime leaders in the Black community, including Ron Herndon, Tony Hopson and former state Sens. Margaret Carter and Avel Gordly.

Supporters laud Smith for creating SummerWorks, a jobs program that has served more than 7,000 young people, while she was at Multnomah County, and helping to secure county and federal funding for a local Promise Neighborhoods initiative that provides programs for more than 1,000 underserved kids annually.

"I'm supporting Loretta because of her demonstrated track record of standing with community when times are tough and fighting for the needs of diverse communities," says Kali Thorne Ladd, founder of the educational nonprofit KairosPDX and former Portland Community College board chair. "Racism has always been part of the fabric of this city, impacting who has had access to what. Now, more than ever, this has been exacerbated by the COVID pandemic. I think we are on an arc towards justice and [Smith] helps bend that arc in the right direction during a time when it is sorely needed."

Like Smith, Ryan has attracted an impressive list of supporters, including former Govs. Barbara Roberts and Ted Kulongoski; House Speaker Tina Kotek (D-Portland); Karis Stoudamire-Phillips; Michelle DePass, the only Black member of the Portland School Board; and City Commissioner Jo Ann Hardesty, who defeated Smith in a bitter 2018 City Council race 62% to 37%.

Those supporters point to a résumé that includes Ryan's leadership on PSU's first capital campaign, which raised $200 million, and his expansion of OBT'S fundraising capacity before he took over at All Hands Raised, formerly known as the Portland Schools Foundation.

He shifted the organization's focus from fundraising to equity and widened its reach to include East County school districts, which have higher levels of poverty and second-language speakers than Portland Public Schools.

Multnomah County Commissioner Susheela Jayapal, who served on the All Hands Raised board, says Ryan focused on equity long before it was fashionable. "He brought a very diverse group of people to the board and to the table when others were wringing their hands and saying they couldn't find anybody."

But some political insiders are motivated as much by reservations about Smith as enthusiasm for Ryan.

Hardesty says that, in her view, Smith is not a good fit at City Hall, where commissioners' oversight of bureaus requires that they collaborate to set policy and run the city far more than is the case at Multnomah County, where the chair holds all the power.

"Loretta Smith doesn't disagree with people, she sets out to destroy you," Hardesty says. "When you set out to destroy someone as an enemy, there's no coming back from that, no opportunity to say, 'Hey, we disagree but where can we work together for the greater good of our community?' That kind of attitude doesn't work on a campaign, and it definitely doesn't work at City Hall."

WW shares Hardesty's objections to Smith.

During her tenure at the county, we reported both on her management style—which two women of color who worked for her characterized in written complaints as bullying and erratic. We also reported on her cavalier use of a county credit card for personal expenses, her frequent and lavish travel, and her use of county money to curry favor with a range of nonprofit groups.

After a series of such negative reports, Smith called in 2017 for a county investigation of the allegations against her—then tried unsuccessfully to block that investigation's report before it could be released.

The investigation found that Smith regularly failed to document expenses, did in fact use her county credit card improperly at least 14 times, and was even more toxic to work with than the two previous complaints against her indicated.

"Several of the allegations raised against Commissioner Smith concern conduct that is potentially discriminatory or harassing in that it is tied to race, gender, religion, sexual orientation, or some other legally protected status," the report said.

It is telling in the current contest that only one of the people who served alongside Smith on the county board in her eight years there, former Commissioner Diane McKeel, is endorsing her.

Smith has been working hard to shift the narrative from 2018, when she ran to Hardesty's right with an endorsement and $20,000 from the Portland Police Association and as a champion of opening the mothballed Wapato Jail as a homeless shelter.

She's switched positions on police and the jail. She now opposes a shelter at Wapato—once her signature issue—and calls for defunding the police, a longtime ally.

Whether Smith's new positions mark a genuine evolution or merely political expediency, we cannot be sure. We couldn't ask her. That's because little more than an hour before her endorsement interview July 20, Smith emailed a letter to WW's editorial board.

"I have decided to no longer seek the Willamette Week's endorsement," Smith wrote. "This moment demands that we name and address racism, discrimination, and violence against black and brown people in all institutions—not just when it comes to the police."

In her letter, Smith pointed directly at WW, citing "the strategic campaigns this paper has waged over the years to discredit, intimidate, and destroy Black leadership in Portland."

"Your paper invests in, and benefits from, systemic racism and institutional bias," Smith added.

As an example, she cited a 2018 illustration of then-Portland Police Chief Danielle Outlaw that ran on WW's cover. Critics blasted the paper for that artwork, saying the illustration reinforced racial stereotypes. The paper apologized. We remain deeply sorry. The cartoon image of Outlaw was an error in judgment.

We disagree with Smith, however, that our coverage of her has been unfair.
For years, this paper has held her accountable, most recently four days before the endorsement interview, in a July 17 story on a puzzling $6,000 cash contribution to her campaign from anonymous sources, seemingly in violation of city and state election rules.

Ryan, whom we endorsed in the May primary, is not perfect. A Black subordinate sued him for discrimination in 2013 (the case settled out of court). And his response to a question about race during this week's endorsement interview produced a collective cringe as he trotted out his version of "Some of my best friends are Black." His answer raised questions whether he understood the import of the last three months—the urgent need to listen to others with different lived experiences rather than assuring them you already understand.

That's an important distinction, because Portland, including WW, badly needs to hear from people it has long ignored. This wrenching year has produced few heroes. But it has shown that some leadership styles match difficult moments. Hardesty's bluntness, for instance, has proven more apt for confronting police brutality than Mayor Ted Wheeler's caution.

In her leadership, Smith has proven to be self-interested and problematic to work for or with.

She says she's changed. "I've had my own struggles and challenges," she wrote in her letter, "and it was not until I truly examined how I show up and the impact of how I show up, regardless of intention, was I able to start making changes that I hope make me a better person and community servant moving forward."

Smith declined to explain those changes to us or to the audience that watches our taped endorsement interviews. The only palpable shift we've seen from her in this election is to reverse some of the core beliefs she held just two years ago.

Ryan, by contrast, has a track record of overcoming adversity and building relationships. He would become the second openly LGBTQ+ commissioner to serve on the City Council and the first openly HIV-positive person to represent the city. He has demonstrated an ability to gather people who disagree and assist them in reaching consensus. Those are qualities the city needs right now.

We endorse Dan Ryan.

Video of our endorsement interview: