On the left, Terrebonne attorney Jamie McLeod-Skinner, the progressive Democrat who vanquished seven-term U.S. Rep. Kurt Schrader, D-Canby, in the May primary.

On the right, former Happy Valley Mayor Lori Chavez-DeRemer, the conservative Republican with hopes of flipping the seat to the GOP.

Polarized politics aren’t the only rift in the 5th Congressional District. There’s the looming mass of the Cascade Mountains that cleaves the district into western and eastern portions. It’s tied together by a thin ribbon of blacktop on U.S. Highway 20 as it crosses the Santiam Pass at 4,817 feet.

By the general election on Nov. 8, the candidates will have to simultaneously track their poll numbers and the chances for black ice or snow drifts on their campaign routes.

The 5th District was created by Democratic legislators in autumn in an effort to tie the bulging number of Democratic votes isolated in Bend with like-minded voters far to the northwest. The resulting seat stretches from Portland in Multnomah County to Sunriver in Deschutes County.

The Democratic and Republican primaries featured one candidate from each side of the mountains. When McLeod-Skinner upset Schrader and Chavez-DeRemer beat Jimmy Crumpacker of Bend, it set up the left vs. right, west vs. east race in the district with the slimmest partisan division in the state. The Cook Political Report, a widely read political forecasting website, puts the Democratic tilt at just 6%.

Both primaries were closed, with only party members allowed to cast ballots to pick a nominee.

Democrats chose McLeod-Skinner, a liberal who is pro-choice, supports gun control efforts and backs President Joe Biden’s agenda of expanded aid to help Americans through the tumult of the COVID-19 pandemic. She supported public health restrictions to curb the spread of the pandemic.

Republicans picked Chavez-DeRemer, a conservative who is anti-abortion, supports gun rights and blames Biden’s spending decisions for steeply rising inflation, including high gas prices. She’s opposed most COVID-19 restrictions as government overreach.

They also highly contrast with their political surroundings. Chavez-DeRemer’s home is in Clackamas County, less than 10 miles from the Democratic stronghold of Portland.

McLeod-Skinner is in the sparsely populated High Desert plateau east of the mountains, with thousands of square miles to the north, east and south sprinkled with steadfastly Republican communities.

Both candidates say they will hold their side of the mountains and run strong on the other candidate’s turf.

“I’ve raised my kids in Clackamas and have built a small business right here as well,” Chavez-DeRemer said “I’ve made long-lasting relationships with key partners in the county. Voters in Clackamas know my track record of common-sense leadership and know how much time I’ve put into giving back to our wonderful community.”

Chavez-DeRemer started making forays over the mountains to Deschutes County almost a year ago.

“We won our primary decisively, sweeping every county and having a strong win in Deschutes County, too,” Chavez-DeRemer said. “I’ve campaigned in Deschutes County at least twice a week since we announced in July 2021, doing meet and greets and knocking on doors, and we certainly won’t slow down.”

Chavez-DeRemer has reached out to Rep. Jack Zika, R-Redmond, the outgoing state representative for much of the congressional district’s eastern side. She’s also garnered support from Deschutes County Commissioner Tony DeBone and Redmond Mayor George Endicott.

McLeod-Skinner remains confident that she can hold the loyalty of most voters on the east side of the Cascades.

“People know me in Deschutes County,” she said. “They saw my campaigns. they see me around town. This is my home.”

McLeod-Skinner ran a high-profile race against former U.S. Rep. Greg Walden, R-Hood River, in 2018 in the heavily Republican 2nd Congressional District that at the time included Bend and Deschutes County. She lost, but held Walden to just over 56% of the vote, the lowest re-election vote in his 20 years in Congress.

McLeod-Skinner did receive some statewide exposure when she ran for secretary of state in 2020. But her campaign was lost in the din of the fight between two Portland political powerhouses serving in the state Senate. Shemia Fagan defeated Mark Hass, with McLeod-Skinner coming in third. She garnered Democratic endorsement for the west side of the mountains even before defeating Schrader. Her endorsement list now runs like a political who’s-who of U.S. senators, former governors, state and local officials from Portland and counties to the south.

The west side of the Cascades will be a challenge — it contains the bulk of 5th District voters.

But the political split favors a Democrat. Republicans have called her a “socialist,” and Schrader suggested after her victory that it was a sign of a “socialist” trend in Oregon Democrats. McLeod-Skinner’s amiable, casual approach in personal appearances is honed from years of campaigning in sometimes hostile political territory.

One issue unlikely to play a big role in the race: Neither candidate technically lives in the 5th District — they can’t even vote for themselves. Under the U.S. Constitution, House members don’t have to reside in their districts, just the state. But in political advertising, such legal distinctions have easily been muddied in congressional campaigns around the nation. But in the 5th District, it’s a lose-lose topic.

Ironically, both live in a stronghold of the other’s party. McLeod-Skinner’s home is in a portion of Crooked River Ranch in Jefferson County, in the 2nd Congressional District of U.S. Rep. Cliff Bentz, R-Ontario, the state’s lone Republican member of Congress. Chavez-DeRemer’s residence is just beyond the 5th District’s northern boundary, in the 3rd District that is a slam-dunk for U.S. Rep. Earl Blumenauer, D-Portland

Both candidates come armed with examples and numbers showing their strengths in the district. In the Democratic primary, McLeod-Skinner won 18,179 votes in Clackamas County — more than the 12,562 who voted for Chavez-DeRemer in the GOP primary. Chavez-DeRemer’s campaign can claim victory in every county of the district, including Crumpacker’s home base of Deschutes County. McLeod-Skinner won the counties at the far ends of the district — Multnomah and Deschutes — while losing in Clackamas, Linn and Marion.

But all totals and trends exclude the 170,033 nonaffiliated voters in the district, a group that is larger than either pool of party voters that was shut out of the closed primaries. They will be able to cast ballots in November. Historically, the nonaffiliated vote usually reflects the same trends as the overall voting pattern in a race.

But in the 5th District there’s more uncertainty than any other congressional district in Oregon. A large nonaffiliated voter group, the forecast of a narrow partisan split, and the new over-the-mountains district lines raise havoc with guessing the political future. Which direction the vote breaks — east or west, left or right — won’t be known until after Nov. 8.

The 5th Congressional District contains parts of Multnomah, Clackamas, Linn, Marion, and Jefferson Deschutes counties.

Total voters: 521,813

Democrats: 169,844

Republicans: 144,776 

Non-affiliated: 170,033

Clackamas County

Total voters: 218,271

Democrats: 76,552

Republicans: 57,167 

Non-Affiliated: 69,577

Deschutes County:

Total voters: 132,781

Democrats: 42,673

Republicans: 36,719

Non-Affiliated: 43,318

Linn County:

Total: 95,805.

Democrats: 21,692

Republicans: 32,543

Non-affiliated 34,045

Marion County:

Total: 37,728

Democrats: 8,816

Republicans: 14,446

Non-affiliated: 12,060

Multnomah County

Total: 37,341

Democrats: 20,208

Republicans: 3,901

Non-Affiliated: 11,029

Notes:

The 5th district also includes minor party members:

Independent Party: 26,919

Libertarian: 3,843

Pacific Green: 1,142

Working Families:1,111

Progressive: 470

Other: 2,969

A small sliver of Jefferson County is in the district with a total of seven voters — three Democrats and four non-affiliated.