With the Nov. 3 election close to a week away, Portlanders are mulling their choices for the next mayor: an incumbent who positions himself as the necessary leader for a steady transition or the challenger, who argues she is a visionary change-agent.
And in an election some pundits thought would bring Mayor Ted Wheeler a clear second win, the race could come to a photo finish as polls show the opponents near dead-even or challenger Sarah Iannarone ahead.
The outcome could be further complicated by an unusually high share of undecided Portlanders – which polls put at about one out of three voters – who could be influenced by a last-minute well-funded political action committee supporting Wheeler, a write-in campaign that’s gained community support for activist Teressa Raiford or campaign finance lawsuits.
In this year’s May primary, Wheeler missed the 50%-plus-one threshold needed to win the seat outright by garnering 49% of the vote. Iannarone, as the second-place finisher with 24% of the vote, advanced to the runoff against the incumbent. Iannarone began campaigning in July 2019 and later enrolled in the city’s public campaign financing program, both of which she has attributed as factors in a stronger showing.
Wheeler, 58, has painted his opponent as ill-prepared to lead the city through varied crises and serve as a key architect of the city’s multi-billion dollar budget since she has never held public office. He and other critics say she has been soft on calling out vandalism and violence committed by protesters during nightly demonstrations over the past five months.
Wheeler argues he has much more experience and will provide needed consistency over another four years to complete partnerships and policies he launched in his first term.
Iannarone, 47, says Wheeler has been an ineffective leader who has lost too much trust from Portlanders and other stakeholders, particularly in recent months, to do the job well. She and other critics say the incumbent has been soft on calling out violence committed by some police officers who respond to during demonstrations.
Iannarone argues that she will bring more bold ideas to achieve the progress and institutional change Portlanders want for their city.
Another key area where the opponents differ is in cuts to the Portland Police Bureau budget – a pressing and controversial topic given the national push to reform law enforcement.
Wheeler was among Portland City Council members who voted in June to reroute $15 million of police funds to other city programs and initiatives and disband three police units. He has since said he doesn’t believe more money should be taken away.
By contrast, Iannarone said she’d listen to community and Black-led groups pushing to cut $50 million from the police budget to fund community investments such as job training.
A SECOND TERM?
Born and raised in Portland, Wheeler is the heir of a timber family. The Oregon coast town of Wheeler is named after his grandfather. He earned a bachelor’s degree in economics from Stanford University, a master’s degree in business administration from Columbia University and a master’s degree in public policy from Harvard University.
Wheeler advised small businesses, managed investments and wrote a book in the 1990s about state and local government before he was elected as chair of the Multnomah County Board of Commissioners in 2006. He unseated then incumbent Chair Diane Linn in the primary.
Wheeler was appointed state treasurer in 2010 by then-Gov. Ted Kulongoski to complete the term of late Ben Westlund, who died of cancer. Wheeler was elected to a full four-year term in 2012. Term limits prevented him from seeking the office again, leading to him running for Portland mayor in 2016.
Wheeler seeks to become Portland’s first mayor elected to two consecutive terms since Vera Katz in 1996. But various polls commissioned by Iannarone’s campaign, the Portland Business Alliance and Oregon Public Broadcasting have shown Wheeler as vulnerable.
Wheeler’s last four years have been rocky at times. He came under fire for his oversight of the police bureau and the city’s response to the housing crisis – both issues that have dogged the past few mayors.
Wheeler touts successes under his watch, including instituting de-escalation and bias training in the police bureau, increasing the city’s shelter capacity and exceeding the city’s goals of housing units built, purchased or renovated under the 2016 voter-approved housing bond.
The mayor received praise for his urgency in addressing COVID-19, including directing city and federal dollars to front-line relief for businesses and families. Yet the pandemic led to increased visibility of the homelessness crisis, leading to frustration from residents, business leaders – and even from Wheeler himself, who threatened to pull city funding from the county-city Joint Office of Homeless Services unless there was more focus on increasing shelter space.
Wheeler also has faced criticism across the board – including from President Donald Trump -- over his inability to find tangible solutions to address the near-nightly demonstrations that frequently became violent and destructive as police and protesters clash. He admitted publicly that he felt his response to city issues was ineffective because he’d been trying to do too much on his own and wasn’t focused enough on calls for police reforms during protests.
The year has also been challenging for Wheeler personally. His close friend, Commissioner Nick Fish, died of cancer in January, and his mother died in June. He also he got divorced.
Iannarone and election finance reform advocates sued Wheeler’s campaign in April, claiming nearly $175,000 in donations he’d received at the time were above the $500-per-donor limit. That lawsuit is pending, as are several subsequent lawsuits against the city auditor alleging campaign finance issues in the mayor’s race.
Among Wheeler’s priorities for a second term are to secure more affordable housing and support services for the homeless, to offer more coronavirus recovery support for small businesses — particularly those owned by Black, Indigenous and other people of color – to create a more sustainable parks system and to launch new public safety reforms.
A DIFFERENT PERSPECTIVE
Born in New York to a working class family, Iannarone moved to Portland in the late 1990s with her then-husband, Nick, after a culinary career that included stints in Missouri and South Carolina.
She returned to college at Portland Community College and then Portland State University, graduating in 2015 with a bachelor’s degree in arts and letters. She is still seeking a doctoral degree from Portland State in urban studies and planning.
She and her spouse opened Arleta Library Bakery & Cafe in 2005 in Southeast Portland. Iannarone and the business were once featured on Food Network’s Diners, Drive-ins and Dives. She and Nick separated three years later and were officially divorced last year. The couple struggled to pay income taxes from 2010 to 2013, according to county tax records.
Iannarone worked as an assistant program director at First Stop Portland, a Portland State office that organizes tours focused on the city’s sustainable infrastructure, and worked as its assistant program director. Iannarone also had a stint as a faculty member at Wayfinding Academy, a Portland-based private two-year college and has served on several city committees including the city’s transportation budget advisory committee.
Iannarone is seeking to be the fourth woman to become mayor of Portland and the first person since Bud Clark in 1984 to be elected without previously holding a prior government job or elected office.
Among several detailed plans, Iannarone has vowed to move the city more aggressively toward meeting climate goals, establish a five-year plan to address the city’s housing shortage, implement a gun buy-back program, advocate for a publicly owned city bank and pilot a yearlong program to offer Black Portland mothers $1,000 a month to fight poverty.
Some critics say her ideas are too far-left for even Portland, such as advocating for decriminalizing sex work and allowing residents to vote in city elections regardless of their U.S. citizen status.
Some have also taken issue with Iannarone’s use of social media, saying her use of expletives and calling out people she disagrees with alienates Portland residents. Some have also questioned why she identifies as “antifa,” which Iannarone described as an ideology opposing fascism, racism and anti-Semitism.
THE FINAL COUNTDOWN
As of Friday, Wheeler’s campaign reported receiving nearly $491,000 in contributions this year. In the last month, the campaign has reported receiving almost $35,000 in donations, according to state campaign finance records.
United for Portland, a political action committee created this month to support Wheeler’s reelection, has raised almost $342,000. Some of the group’s biggest backers include political action committees for the Portland Metropolitan Association of Realtors ($150,000) and the Portland Business Alliance ($50,000), as well as the Oregon chapter of the National Association of Industrial and Office Properties ($10,000) and Columbia Sportswear CEO Timothy Boyle ($10,000).
Iannarone’s campaign has reported receiving more than $774,000 this year, including more than $132,000 this month as of Friday, state campaign finance records show.
Iannarone is enrolled in the city’s public campaign finance program, which provides a six-to-one match for cash contributions of $50 or less. Wheeler is not.
*Note*: A previous version of this story misstated Iannarone’s role with First Stop Portland.
--Everton Bailey Jr.