Steve Dipaola/AP Photo
Democratic congressional candidate Jamie McLeod-Skinner poses after a debate at Lakeridge High School in Lake Oswego, Oregon, October 17, 2022.
PORTLAND, OREGON – “My mom taught me to always leave a place better than you found it,” Jamie McLeod-Skinner told me on a front porch in Portland at the end of September. It was a familiar refrain, one she’s uttered on several debate stages and in countless town halls. It made an appearance during an interview with me in May, hours before polls closed in a primary win over centrist Democrat Kurt Schrader that sent shock waves through national politics. And it was the line she used to open our very first conversation in March, months before she or anyone else could foresee the outsize importance her race would have on the narrative of this year’s midterm elections.
Just as I began to think this mantra was a classic example of a candidate’s obsession with message discipline, McLeod-Skinner opened up a little further. “Throughout my life,” she said, “I’ve made the decision to engage in public service—to take on some of the hard battles just because they need to be taken on.” That life of service, she explained, was the natural result of watching her mom struggle to provide a stable life for her and her brother while growing up in rural Wisconsin.
“My mother left a violent marriage when I was very young,” she told me. “She worked three jobs for a lot of my childhood, and when I was nine we moved overseas for her to teach. It’s there that she met the man I call my dad.” McLeod-Skinner spent her formative years with her mother in Tanzania and Kenya, before moving to southern Oregon midway through high school. After graduation, McLeod-Skinner pursued a bachelor’s degree from Rensselaer Polytechnic Institute and then a master’s degree from Cornell University, which she received in 1995.
She describes that year as something of a crossroads. “When I graduated I had choices to make,” she reflected. “My colleagues were all going into the corporate sector … I went to Bosnia.” She would spend the next two years managing reconstruction programs in Bosnia and then Kosovo, before returning to the United States to run a refugee resettlement office in San Jose, California, in 1998. In 2004, she made her first foray into public office by winning a seat on the city council in Santa Clara, California—a position she held for eight years.
But Oregon always felt like her “home base,” she told me, and when she decided to return to school to get a law degree in 2013, she chose the University of Oregon. That allowed McLeod-Skinner to be close to her mother, who has retired from teaching and now lives in Bend—the anchor of the district her daughter is running to represent.
Her career in Oregon has included stints on the state Watershed Enhancement Board, an education board in Jefferson County, and as the interim city manager in Talent, following the devastation the community faced after wildfires in 2020. “I think there’s power in these small acts of service,” she says, by way of explaining her eclectic résumé. “What I have found, working with folks in the most progressive and the most conservative parts of our state and the most urban and rural, that regardless of party affiliation, we all want to be able to put a roof over our head and food on our table, we want opportunities for our kids, want health care for our families. We don’t want our homes to burn down.
“And to message that correctly,” she continued, “you really have to have shown up.”
But in politics, showing up with a compelling résumé and a genuine message is only half the battle. As the only Democratic primary challenger to successfully oust an incumbent this year, she has been all but left for dead by the national party, which has refused to invest in her race, even as the typical indicators of potential—fundraising, polling, and grassroots energy—show her race is winnable. McLeod-Skinner has, by all accounts, done everything right. Everything, that is, except wait her turn as a seven-term incumbent uses a seat he bought with an inherited pharmaceutical fortune to undermine his party and sell out the constituents he was elected to serve.
If McLeod-Skinner wins, it will be a triumph for populist Democrats, who harbor an ideological attachment to the grassroots-mobilization politics that seem increasingly futile in the face of the rapidly escalating fortunes special interests are pouring into political campaigns. And if she loses, her loss will be used as a cudgel against future insurgents, even though the party establishment has left her twisting in the wind during a cycle that is shaping up to be brutal for Democrats—especially in Oregon.
“A Campaign Years in the Making”
McLeod-Skinner’s lifetime of public service made her an attractive nominee to contest Oregon’s blood-red Second Congressional District in 2018—a role usually filled by perennial candidates, washed-up former elected officials, or young political hopefuls looking to use the thankless contest to build the relationships necessary to win in the future. While McLeod-Skinner might justifiably be accused of the latter, the seriousness with which she ran that quixotic campaign is hard to fault. Before her run, ten-term incumbent Greg Walden had never won a re-election campaign by less than 35 points. He ultimately bested McLeod-Skinner by just under 17.
In 2020, she leveraged the respectable effort against Walden to run for secretary of state—a managerial role that she felt suited her professional background. She ultimately finished third in a tight three-way primary, carrying several of the counties she ran to represent in the Second, but failing to build beyond that base.
Two consecutive losses is usually enough to end a political career, but Oregon’s new congressional lines, whose boundaries were upended by the addition of an entirely new district, gave McLeod-Skinner a rare third bite at the apple. After redistricting, the Fifth Congressional District now extends south and east from Clackamas County instead of jutting west to the coast. The swap left Schrader defending a broad swath of territory in central Oregon that had previously comprised McLeod-Skinner’s base of support in the old Second District. Those scrambled boundaries, combined with a series of self-inflicted political wounds by Schrader, created an opening.
As Oregon Independent Party spokesperson and co-founder Sal Peralta put it, when McLeod-Skinner announced, it “felt like a campaign years in the making … She had spent years building a grassroots network of support, and she built a reputation for herself as a real working-class champion.”
McLeod-Skinner’s primary win over centrist Democrat Kurt Schrader sent shock waves through national politics.
That reputation inspired local Democrats to support a candidacy that drew the ire of national party leaders. The activist-led county Democratic parties took the unprecedented step of changing party bylaws—a time-consuming process that demands a two-thirds supermajority of voting members in each county—in order to endorse McLeod-Skinner. In unprecedented fashion, she secured official endorsements from the four largest county Democratic parties in the district, and rode a wave of support from grassroots organizations like Indivisible and the Working Families Party to a lopsided ten-point win over Schrader—making him the first Oregon incumbent to lose a primary election in over 40 years.
Much like Schrader, McLeod-Skinner’s general-election opponent, Republican Lori Chavez-DeRemer, is an excellent foil for the working-class populism McLeod-Skinner evokes. But during the early stages of the race, McLeod-Skinner focused her attacks on Chavez-DeRemer’s supportive statements for January 6th insurrections, and her ever-changing stances on abortion, rather than the fact that she is a multimillionaire owner of private health clinics.
At times, McLeod-Skinner has struggled to hide her annoyance at Chavez-DeRemer’s loose grasp on the intricacies of policy. At a debate hosted by Portland television station KATU, Chavez-DeRemer repeated viral conspiracies about “rainbow fentanyl” appearing in children’s Halloween candy. At a separate debate aired by Bend’s KTVZ, she displayed visible confusion over which level of government has jurisdiction over basic housing policy issues. And in their endorsement forum with The Oregonian, Chavez-DeRemer insisted that her skepticism of man-made climate change does not mean she is a climate denier.
The editorial boards of local newspapers, all of which have endorsed McLeod-Skinner, have highlighted that policy gap. The Oregonian—Oregon’s paper of record—was especially harsh in its appraisal of Chavez-DeRemer’s campaign, saying she “spoke primarily in generalities” and provided answers that “seemed more relevant for someone running for local or state office rather than Congress.” McLeod-Skinner, by contrast, was praised for how “easily [she] delves into specifics of the ideas she supports or the factors that influence decision making.”
But if newspaper endorsements and policy fluency won elections in rural America, Donald Trump would never have been president.
National Democrats Head for the Exits
Years of preparations and a series of lucky breaks can do only so much, however, in the face of a daunting national, and statewide, environment.
As Democratic electoral committees scramble to shore up blue-leaning seats that should be safe bets, they have been quick to cut off progressive candidates in tough races, while providing little in the way of justification. While the Democratic Congressional Campaign Committee, or DCCC, has invested nearly $2 million in the race in Oregon’s Fifth, the leadership-aligned House Majority PAC, or HMP, has declined to spend in the race at all—making her run the most expensive contest, by far, that lacks the blessing and financial support of House Democratic leaders.
Some of that money earmarked for McLeod-Skinner’s race has been funneled instead into a closer-than-expected race between progressive state representative Andrea Salinas and scandal-plagued millionaire Mike Erickson in the district next door. In addition, local parties have been distracted by a free-for-all gubernatorial race where an unpopular retiring Democratic incumbent and a centrist third-party candidate on the ballot is creating the probability of handing Oregon’s governor’s mansion to a Republican for the first time in recent memory.
Those races, along with a tough national environment for Democrats, who have fallen behind as voters focus on inflation and crime, have drained attention and resources that would have otherwise been reserved for McLeod-Skinner, leaving her and the grassroots organizers that powered her primary victory to contest the district alone.
While national Democrats’ abandonment of the district has been a key factor in many forecasters’ decisions to shift the race into the “lean Republican” column, Republican committees continue to invest in a manner that suggests they still view the race as a toss-up. Last Thursday, the Congressional Leadership Fund, House Republicans’ counterpart to HMP, shoveled another $636,000 into the district. That investment brings the total expenditures by outside Republican groups to just under $8 million—an amount surpassed in only 16 other seats this cycle.
Despite the headwinds thwarting her run, local activists appear to think she can still win. According to Clackamas County Democratic Party Chair Jan Lee, McLeod-Skinner’s record of overperforming expectations is a large part of why local activists went out on a limb to support her candidacy in the first place.
“We looked at her last run for office and were very impressed by the way she performed in the new parts of the district,” Lee told me shortly after the county party bucked Schrader—a longtime Clackamas resident—to endorse McLeod-Skinner this spring. “We felt that with her on the ballot, young people and disengaged people might take a second look.”
During her 2018 run, McLeod-Skinner became the first Democrat in recent memory to win Deschutes County, even as now-retiring Gov. Kate Brown lost that same turf by ten points on her way to an underwhelming six-point victory.
This year, that base seems to be showing up—at least so far. While Republicans have built up a steady lead statewide in the percent of ballots returned by their party’s registered voters, Democrats in the handful of counties comprising Oregon’s Fifth District have bucked that trend by keeping their return percentage close to even. And in Deschutes, Democrats have managed to open up a slim lead of their own in proportional ballot returns. Overall, comparative turnout across the district so far more closely resembles 2018 and 2020 than the last red-wave election.
“We’re All Talking About the Same Things”
Perhaps the only question McLeod-Skinner has struggled to answer throughout the race is whether she is a progressive.
Debates over her ideological position erupted the day after her primary win, and her scrappy populism has become a Rorschach test for those eager to read national trends into her hyperlocal campaign. Progressives, struggling for silver linings to a primary season defined by heavy-handed interference from billionaire-funded super PACs, were quick to celebrate her ousting of Schrader as a victory for their embattled movement. Moderates, wary of narratives about the party being pulled to the left ahead of a fraught midterm season, were quick to point to how McLeod-Skinner has distanced her brand from moderates and progressives alike.
Straddling that line has at times proved awkward, as was the case during a recent forum, where a moderator grew increasingly exasperated while trying to solicit a yes-or-no answer to the question of whether McLeod-Skinner identifies as progressive—ultimately to no avail.
McLeod-Skinner seems to bristle at discussions of ideological positioning, as if the very idea of framing the issues facing regular working people as relegated to one part of the political spectrum genuinely bugs her. “People don’t realize that we’re all talking about the same things,” she once told me, “so why not talk about it in language that makes sense to everyone?”
When asked how she differs from her party, though, McLeod-Skinner almost always offers critiques from the left. Our front-porch conversation in Portland happened to take place the day after the House’s Democratic leadership unceremoniously hobbled efforts to pass a ban on members trading stocks—one of the hallmark issues of her campaign.
“These are the things that drive me nuts about the Democratic Party,” she said, while rolling up the sleeves on her Service Employees International Union hoodie. “If you’re a member of Congress and you want to go trade stocks, then do it. God bless you. But just let someone else represent your district then, OK?”
Despite the headwinds thwarting her run, local activists appear to think she can still win.
The contours of her ideology shine through in most policy discussions. Rather than distance herself from Democratic legislation like the Build Back Better Act or Inflation Reduction Act, she is quick to talk about where they did not go far enough. Letting Medicare negotiate the cost of a few drugs and capping the price of insulin in the IRA is a start, she says, but real reform would mean implementing price controls that apply to all prescription drugs.
When she appears in front of a crowd, McLeod-Skinner is quick to highlight that she is not only the nominee of the Democratic Party, but also the Independent Party and Working Families Party. According to Peralta, the Independent Party spokesperson, that gesture is key to capturing Oregon’s growing number of unaffiliated voters.
If there is one clear area in which McLeod-Skinner does differentiate herself from national progressives, it is the way that she moves, as if by instinct, to disarm identity-focused discussions. When asked whether her happy-warrior demeanor was forged through the years of hardship LGBTQ people often endure growing up in rural areas, she batted away the premise. Rural sensibilities, she insisted, were deeply misunderstood by most Democrats. “My neighbor two doors down has a Trump flag,” she told me, “but she’s a good neighbor. She’s respectful to my wife, and she’s kind to my kids.”
“In rural areas,” she explained, “if it’s winter and you’ve got a flat tire, someone’s going to stop and make sure you’re safe—they aren’t going to check which bumper stickers are on your car first.”
In the race’s final weeks, McLeod-Skinner has acted emboldened in the face of clear disadvantages. Some of the unifying rhetoric that defined her early general-election strategy has melted away in favor of the punchy populism that animated her primary win, focusing on Chavez-DeRemer’s wealth and power. It’s not clear whether that will be enough to turn around entrenched opinions. But she’s also using as a closing message her ever-present credo that speaks to the promise and peril of this midterm cycle: “I’ll leave Congress better than I found it.”
