Both candidates have pushed themselves to court new constituencies beyond their bases, but the approaches have also exposed their vulnerabilities.

In her second quest to defeat Oregon Gov. Tina Kotek, Sen. Christine Drazan, R-Canby, has gone straight into the political lion’s den.

She has announced policy plans to reduce taxes and regulations in the heavily-Democratic Portland metropolitan area, emphasized the natural beauty of its waterfront and advocated against needle exchanges near schools in Multnomah County.

But those appeals haven’t always gone smoothly. At one speaking event in Portland, attendees peppered her with questions about her relationship with the national GOP. During a September meeting at a Southeast Portland church, one voter accused Drazan of misrepresenting her life story about politicians failing a timber industry that left her Klamath Falls hometown.

Despite the effective rematch from 2022, this year’s gubernatorial campaign trail has pushed both Drazan and Kotek to appeal to the opposite side of their ideological lanes. Polling a few weeks out from the Nov. 3 election showed the race in a statistical tie, and the two women’s rhetorical skills are being tested in ways that their allies say are naturally uncomfortable for the candidates.

Drazan’s has been campaigning in person while supporting downballot Republicans and focusing on metropolitan areas. She no longer has to fortify support in rural areas where she may have lost votes to nonaffiliated challenger Betsy Johnson in the 2022 race, but that has opened her up to at times hostile interactions from skeptical voters in the state’s most populous county.

“Is it easy? Absolutely not. Is it comfortable to go into those settings as a Republican? Absolutely not,” said former Republican Rep. Knute Buehler, a Drazan ally who lost to former Gov. Kate Brown in the 2018 election and has since left the Republican party. “But it’s absolutely essential to do.”

Kotek also faces significant headwinds. She is seeking to appease business-friendly voters in suburban and urban areas of the state while motivating a fractured progressive base in Portland. Many of her appearances have focused on interviews with sympathetic social media influencers rather than campaign press conferences or public events.

Ahead of her first term, Kotek named housing and homelessness, behavioral health and education as her top three priorities. But during her nearly four years in office, Oregon has struggled to make progress on each of those issues.

Tens of millions in new state funding netted thousands of new shelter beds and kept tens of thousands of Oregonians from eviction, but the most recent federal count of homeless individuals found thousands more people lacked homes in 2025 than in 2023. Oregon students’ grasp of reading, writing, math and science has improved slightly since immediate post-pandemic lows, but they’re still far behind their peers.

The governor has spent most of the campaign trying to tie Drazan to the Trump administration and began to deviate from that messaging in her final two debates earlier this month. Her supporters say the task of showing progress is not within her natural skillset.

“She’s an in-the-weeds person, and she’s a big picture person, and she is terrible at taking credit for it,” said former Portland Democratic Rep. Barbara Smith Warner, who was House majority leader when Kotek was House speaker. “You can get plenty of stuff done if you don’t take credit, and yet there’s a point where it is different when you’re a leader.”

Kotek argues continuity will be key to solving Oregon’s challenges

Kotek first came onto Oregon’s political scene as an advocate for the Oregon Food Bank in the late 1990s after moving from Pennsylvania, eventually winning election to a Portland-area House seat in 2006.

She later became the state’s longest-serving House speaker from 2013 to 2022 and shepherded major progressive policies, such as the nation’s strongest set of sanctuary protections for immigrants and a universal paid leave program, through the Legislature. She’s one of the nation’s first two openly lesbian governors.

She’s also among the least popular governors in the nation, polling has shown throughout her term.

In an interview, Kotek conveyed a sense of urgency for building on her work, such as getting Oregon to buck a national trend to increase initial housing starts for 2026. The estimated nearly 9,700 home permits pulled so far this year still puts Oregon far below her initial goal of 36,000 new homes per year to address decades of underbuilding.

Kotek argues that she needs more time.

“I’ve never said that the mission is accomplished, but what I have said is we have to keep working together to make progress,” she said. “Progress takes persistence, that takes leadership and continuity.”

But that continuity has also been marked with some scrutiny over the role some of Kotek’s closest allies, including first lady Aimee Kotek Wilson and labor union leaders, have played in the Oregon government.

Several of Kotek’s top advisers left her office over her 2024 attempt to elevate her wife’s authority by creating an “Office of the First Spouse” and giving Kotek Wilson, who has a background in social work and shared in 2024 that she was in recovery from alcohol use disorder, a role in crafting behavioral health policy.

The Oregon Government Ethics Commission dismissed complaints against Kotek on the grounds that there was no evidence that Kotek or her wife would benefit from an unpaid volunteer position. The governor has since tapped the first lady to lead a council aiming to address workforce issues for behavioral health services in Oregon.

When it comes to unions, meanwhile, Kotek has faced backlash for their influence on a variety of issues, such as unemployment benefits, public projects and legislative districting.

Her support for a 2025 first-in-the-nation law offering unemployment benefits to striking public and private workers, for instance, reignited longstanding concerns that she wasn’t serving as an effective check on their interests. Critics see the law as a giveaway to unions that will strain public agencies and the state’s unemployment insurance fund.

Kotek also issued a 2024 executive order that required many state construction projects to be built with union labor, a type of proposal which industry groups have long criticized for driving up costs. After a coalition of organizations led by the Oregon-Columbia chapter of the Associated General Contractors sued, a Marion County judge blocked the order in March.

Unions were also thorn in the side for some in Kotek’s party during a special 2021 legislative session near the end of her tenure as House speaker, when state lawmakers sought to redraw legislative and congressional maps.

Former Rep. Marty Wilde, D-Eugene, said he saw the hand of influential unions who support Democrats in the decision to redraw his Eugene-area district into one favoring Republicans and box him out of the Senate seat he was considering seeking. The Oregonian/OregonLive reported that the executive director of the state’s largest public employee union had been advising House Democrats d...

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