10 essential questions about Oregon’s 5th District, the state’s most unpredictable congressional race

By Emily Cureton Cook (OPB)
April 26, 2022 12 p.m.

Ballots will soon be circulating for Oregon’s first primary election since state lawmakers redrew congressional boundaries — greatly altering the 5th District and creating a new one. This change in boundaries for the 5th District set the stage for a battle between the major parties in November, as national Republicans eye the rejiggered district in their quest to regain control of the U.S. House. But first, six-term Democratic incumbent Rep. Kurt Schrader faces a primary challenge from the left, and a mutiny among grassroots organizers in his own party.


OPB sat down with candidates for the newly drawn 5th District, and political experts from both sides of the aisle to answer 10 essential questions about Oregon’s least predictable congressional race in the May 17 primary.

Side-by-side maps of Oregon shows the boundaries of the state's five congressional districts in 2020 and six districts in 2022.

U.S. Rep. Kurt Schrader has won the 5th District handily since 2008. Why is his seat in jeopardy now?

Three primary candidates besides Schrader are pouring cash into the race — Democrat Jamie McLeod-Skinner and two Republicans, Lori Chavez-DeRemer and Jimmy Crumpacker. McLeod-Skinner wants to wrest the party’s nomination in May, and the Republicans are vying for a shot to flip the seat in November.

Last year, the Democratic-controlled redistricting process took metro areas of Central Oregon away from the solidly Republican 2nd Congressional District, realigning Bend and Redmond with counties west of the Cascades. The new 5th District leans blue, but according to the Cook Political Report, it’s less secure than before.

More than half of all voters in the redrawn district haven’t seen Schrader’s name on the ballot before, but they have seen other campaigns by his primary opponent, Jamie McLeod-Skinner. At the same time, the longtime congressman faces an image problem within his own party, even as he continues to enjoy national leaders’ support. President Joe Biden endorsed Schrader after county-level leaders took the surprising step of backing McLeod-Skinner.

What led to county Democrats breaking with Schrader?

Jamie Mcleod-Skinner, Democratic primary candidate in Oregon’s 5th congressional district.

Jamie Mcleod-Skinner, Democratic primary candidate in Oregon’s 5th congressional district.

Courtesy of Jamie McLeod-Skinner

In a highly unusual move, Clackamas, Deschutes, Linn and Marion County Democrats have endorsed McLeod-Skinner.

“Kurt Schrader is not voting to protect the people in our county,” said Clackamas County Democrats Vice Chair Cris Waller. “He is voting to help the people who have funneled money into his campaign.”

Waller said she believes the congressman is in the pocket of big business, and that his name won’t motivate voter turnout. She helped author an eight-page list of reasons why grassroots organizers in Schrader’s home county decided to pull their endorsement. On the other side of the mountainous district, Deschutes County’s Democratic central committee backed McLeod-Skinner by an even wider margin.

“There was a strong desire, not just for a Democrat, but for one that was seen as more progressive, and not standing against [President] Biden’s agenda,” county chair Jason Burge said.

Progressive critics have zeroed in on Schrader’s relationship to the pharmaceutical industry, a leading funder of his campaigns. Records show a connection to his office. Last year, Schrader’s longtime chief of staff Paul Gage also left his role and went to work for PhRMA, the industry’s most powerful lobbying arm. And in 2021, Schrader cast a deciding vote to shut down a prescription drug pricing plan Democrats have long sought. He also voted against a piece of President Biden’s spending bill that would have allowed Medicare to negotiate drug prices. A year ago, he was one of only two members of his party to vote against a $1.9 trillion pandemic relief bill because, among several reasons, he did not support including an increase to the minimum wage.

The controversies did not stop Biden from endorsing Schrader after the county leaders pulled support.

“We don’t always agree, but when it has mattered most, Kurt has been there for me,” Biden wrote in his announcement. “And in doing so, he has helped to pass much of my agenda into law — making a huge difference in the lives of the Oregonians he represents and all of America.”

How does Schrader respond to criticisms from Oregon Democrats?

The congressman told OPB that the county organizers “represent the extreme far left of the party.” He cast himself as a moderate Democrat who compromises to get things done.

“In Oregon, at least in my district, people want results,” Schrader told OPB.

Kurt Schrader, Democratic primary candidate in Oregon’s 5th congressional district.

Kurt Schrader, Democratic primary candidate in Oregon’s 5th congressional district.

Steve Dipaola / Courtesy of Kurt Schrader

He justified voting down the drug pricing plans backed by the broader Democratic coalition in 2021 because, in his view, the legislation was doomed in the Senate. He sponsored a more limited bill in the House that would cap the cost of insulin and limit out of pocket expenses for seniors on Medicare, but it has not become law.

“I worked with the Senate to make sure that this bill is acceptable to them. So it will pass,” Schrader said.

He pointed to being a founding member of the Problem Solvers Caucus, a group of lawmakers evenly split between the major parties with a mission to find common ground. Schrader also took credit for brokering an agreement last year on the embattled bipartisan infrastructure bill.

“I had a personal stake in that, and it would never have happened if Kurt Schrader had not been a member of Congress,” he said.

How big of a role is money playing in this race?

The 5th District could ultimately be among the most expensive political contests in Oregon of 2022. Attacks over campaign financing are central to the Democratic insurgent’s campaign, but Schrader doesn’t need local party leaders’ goodwill to maintain a distinct money advantage, including donations through the Democratic National Committee. His campaign reported about $2.7 million cash on hand as of March 31, which is three times what’s in the other candidates’ campaign coffers combined.

As of the latest filings with the Federal Election Commission, Schrader had outspent his only primary opponent, McLeod-Skinner, 12-1. More than half of his war chest came from political action committees. About a third, some $772,000, came from individual contributions.

McLeod-Skinner’s campaign had raised $545,500 total, with 96% of her total receipts coming from individual contributions.

On the Republican side, two candidates reported the vast majority of financing: Crumpacker narrowly led the GOP fundraising with $467,000 in receipts. Chavez-DeRemer was raising and spending a similar amount, with $455,000 in receipts.

Schrader’s campaign was the first to douse the district in ads, some of which say he has a record of being tough on pharmaceutical companies. This has rankled critics who call the claims misleading at best. Residents of the 5th District are also being flooded so far with some $680,000 in ads paid for by a political action committee, Center Forward, which supports Schrader. The group doesn’t disclose its donors publicly.

How is Jamie McLeod-Skinner approaching her campaign?

McLeod-Skinner has pledged not to take money from corporate PACs. Much of her messaging attacks Schrader by linking his voting record to campaign financing and perceptions of special influence for funders.

“Our politics has become pay to play,” she said in an interview. “Sometimes we see too close of a connection between where people’s money comes from and how they’re voting.”


McLeod-Skinner has run underdog campaigns before: for Oregon Secretary of State in 2020 and for the solidly Republican 2nd Congressional District in 2018. Neither was successful, but the 2018 campaign in particular showed she can be effective at grassroots campaigning.

She said the most important challenges facing Oregon now are economic recovery, protecting democracy from voter suppression, money in politics and climate crisis action.

“There’s a lot of crises that are going on right now that people want an accountable, responsive and trustworthy government to respond to,” McLeod-Skinner said.

She has picked up some major endorsements from the Democratic establishment, including Massachusetts Sen. Elizabeth Warren.

Oregon's U.S. House District 5 under the 2022 redistricting map.

Which factors are most likely to sway Democratic primary voters?

Democratic analysts are split on what the winning formula will be in Oregon’s 5th District.

“All the endorsements in the world aren’t going to matter if your opponent is outspending you 30 or 40 to one,” said Brian Smith, a member of the Muscogee Nation and a consultant with a focus on Native and other BIPOC progressive candidates in Oregon.

He was a field director and data manager with McLeod-Skinner’s 2018 congressional campaign, but isn’t involved with her race now. He said the victorious candidate will need to win over voters who haven’t followed politics, and aren’t already familiar with either candidate.

“What they’re seeing is what’s on TV, the digital ad buys, the mailers — this is going to define the message,” Smith said.

Meanwhile, Oregon State University-Cascades political science instructor Judy Stiegler pointed to Central Oregon’s recent track record of bucking candidates with the most money. In the 2020 GOP primary for the 2nd District, the leading fundraiser did not win the nomination, and in Bend, a 2020 Oregon House race ousted Republican incumbent Cheri Helt, despite a significant fundraising advantage.

The big risk of a Democratic primary showdown, she said, is that it could give Republicans a better chance to flip the seat in November.

“The Republican candidates are salivating over this,” Stiegler said.

Who are the Republicans in this race?

There are five Republican candidates in the mix. OPB interviewed two candidates whose campaigns show the most activity in terms of ground game, online presence and financing: Chavez-DeRemer and Crumpacker. A third candidate, John Di Paola, had raised about $53,000, and did not respond to emails from OPB.

Chavez-DeRemer was the mayor of Happy Valley in Clackamas County for eight years, until 2018. She served on the City Council before that, and has run twice for a state legislative seat in House District 51.

Crumpacker is a financier with property in Deschutes County, who brands himself as a political outsider with roots in Oregon. He ran a primary campaign for the 2nd Congressional District in 2020, buoyed by over $300,000 in personal loans to the race, which he lost to now U.S. Rep. Cliff Bentz.

How contentious is the GOP primary so far?

The sparring is much more subdued than what we’re seeing on the other side of the ticket. Republican political strategist Rebecca Tweed said candidates are more focused on the November prize of unseating a Democrat than on attacking each other.

“If I’m the Republican, I’m trying to treat it like it’s an open seat,” Tweed said. “You attack Congressman Schrader where you think he’s been weak, but you don’t want to give him more name recognition than what he can earn himself.”

Tweed said the winning GOP nominee will need consistent messaging, but that’s tough when they want to appeal to conservatives in Bend, those in the Portland metro area and rural voters.

Crumpacker and Chavez-DeRemer both said inflation is the biggest problem facing Oregon. Both want to to rollback regulations on the timber industry and allow more logging. Both talked about ramping up domestic oil production, and both said they would support more oil and gas pipelines to do that.

What sets the Republican campaigns apart?

Lori Chavez-DeRemer, Republican primary candidate in Oregon’s 5th congressional district.

Lori Chavez-DeRemer, Republican primary candidate in Oregon’s 5th congressional district.

Courtesy of Lori Chavez-DeRemer

Chavez-DeRemer is emphasizing her experience managing a city and her family business in Oregon. She is also hitting national talking points popular with supporters of former president Donald Trump. When asked if President Biden won the 2020 election, she didn’t give a clear answer.

“I think that there’s some question to what people felt. People were, at least voters I talked to, they felt like it was unusual,” she said.

False claims of election fraud by President Trump fueled a deadly riot in the U.S. Capitol on Jan. 6, 2021. Chavez-DeRemer questioned the trustworthiness of Oregon’s vote by mail system, which has not been subject to widespread fraud, but has been credited with skyrocketing voter turnout in the state.

OPB asked Chavez-DeRemer how she sees herself compromising across the aisle if elected.

“I don’t know about the word compromise. You can’t compromise the Oregon 5th’s voice,” she said.

How did Crumpacker respond to questions about false claims of election fraud?

Crumpacker did not hesitate to say President Biden won in 2020.

Jimmy Crumpacker, candidate for Oregon’s 5th congressional district.

Jimmy Crumpacker, candidate for Oregon’s 5th congressional district.

Emily Cureton / OPB

“I have a lot of confidence in the Supreme Court of the United States,” he said, referring to the court’s decision to reject a handful of election-related cases brought by supporters of the former president.

This is a shift from Crumpacker’s image in his 2020 GOP primary run, when he branded himself as a stronger Trump supporter than his rivals in a crowded Republican field. Now, he’s hitting talking points more in line with former Vice President Mike Pence, and promoting his business experience as a commodities trader specializing in oil.

“My background in energy and in finance, and in world affairs, puts me at a different level than my opponents,” Crumpacker said.

When asked how he plans to compromise with the other party, he said: “I would be shocked if other members of the Oregon delegation didn’t have the same goals of reducing inflation, stopping forest fires.”

All of the Democrats in Oregon’s delegation have been in office more than a decade, including Schrader. Crumpacker has signed a pledge to support term limits. Chavez-DeRemer has not. She said she understands the frustrations with entrenched incumbents, but it’s up to voters to make change.