Gerrymandering Democrats Tighten Grasp On Rural Oregon

In Central Oregon, horses and Trump flags are more common than electric cars and pride flags. But perhaps not for long.

At least geographically, most of Oregon is similar. A small slice of the state lies west of the Cascade Mountain Range, featuring the expected dreary weather and socialists of Portland. But most of the state lies east of the Cascades, where high desert and plains sprawl for miles, dotted by ranches and sagebrush. 

Central Oregon, a historically conservative area, is where the beautiful scenery to the west meets the high desert and rugged independence to the east. But when state Democrats redrew congressional districts in 2021, they gerrymandered Congressional District Five to include part of leftist Portland and much of Central Oregon. 

For the first time in recent history, much of Central Oregon will find itself represented by a Democrat. State Rep. Janelle Bynum unseated Republican U.S. Rep. Lori Chavez-DeRemer, who narrowly won the district in 2022.

Deschutes County, the most populous region of Central Oregon, had gone red in every presidential election since 1964. But in 2020, a shifting population led to Democrats outnumbering Republicans for the first time in the county — and it went blue in both 2020 and 2024. 

So, from gerrymandering to flooding Central Oregon with leftist voters, Oregon Democrats are gaining a hold on the area.

Transforming a Region

The city of Bend was conservative until 2008, when it elected a Democrat to the state House. It has since been known as the only blue dot east of the Cascades. Former Bend Mayor Jeff Eager, a Republican, told The Federalist this was not always the case.

Eager was elected to Bend’s city council in 2008, and he served as mayor until 2012. He said Bend, and the rest of Central Oregon, had been “solidly Republican” until recently.

“Democrats and left-leaning independents have continued to increase their margin since, and Bend is now a pretty progressive city,” Eager said. “Bend is the largest city in Central Oregon, so it’s dragged the entire region leftward.”

Central Oregon is the state’s fastest-growing region, in large part because of its natural beauty, which draws tourism for outdoor recreation. Eager said this has sparked “political, cultural, and economic change” within a “relatively short period of time.”

“Central Oregon has long been an attractive destination for people fed up with life in big, progressive west coast cities. Many of those people, ironically, vote in a manner destined to make Central Oregon like the places they fled,” Eager said. “Many long-time residents are mystified by what’s become of their area.”

Bend, with just more than 105,000 people, is now a hub for the drugs and homelessness typically found in larger leftist cities. A tragic example is former Bend Mayor Craig Coyner III, who held office in 1984 and served on the city council for decades, according to KGW8. Last year, he died homeless.

Fortifying Democrat Control

Eager blamed “in-migration” to Deschutes County for the recent blue tide in the area. He said Democrats now have a “several-point” advantage in voter registrations.

“In-migration to Bend, but also Redmond and Sunriver, from heavily Democratic urban areas like the Bay Area, Los Angeles, and Seattle, has fundamentally changed the political makeup,” he said. 

When Oregon Democrats redrew the state’s U.S. congressional districts in 2021, they gerrymandered the district so it ran from southern Portland into the Willamette Valley and across the Cascades to Central Oregon. Eager said this move was intended to create a “swing district” that Democrats think “will become more blue over time due to rapid left-leaning in-migration to Bend.”

“They had to lump Bend and other parts of Deschutes County in with communities west of the Cascade Mountains, breaking a many-decades tradition of honoring the difference between Western and Central and Eastern Oregon,” Eager said. “It looks like the Democrats’ strategy paid off this cycle.”

Eager called Bynum a “run-of-the-mill Oregon progressive, and not a particularly impressive one.” According to the Oregon Capital Chronicle, Bynum allegedly ignored reports that one of her operatives sexually harassed and assaulted a volunteer, who was a minor, during the 2022 campaign. 

“Democrats have used their seemingly permanent majority status in Oregon to redistrict legislative and congressional districts to maximize their advantage,” Eager said. “This has contributed to gradual attrition of former GOP office-holders, including [in] this cycle Chavez-DeRemer. But this would not have been possible without the rapid growth of Democratic voter registration.”

Seeking Solutions

Despite recent Democrat efforts to transform Central Oregon, much of the area — and the rest of Eastern Oregon — remains deeply Republican. In this month’s election, former President Donald Trump won many counties east of the Cascades by more than 70 percent. 

Matt McCaw is the leader of the Greater Idaho Movement, which seeks to help counties in Eastern Oregon join their conservative neighbor, Idaho. So far, 13 counties have passed measures in support of considering the proposition. McCaw told The Federalist he thinks Congressional District 5 is “completely gerrymandered” to assert control over Central Oregon.

“Western Oregon is using every political tool that they have to gain more political power to advocate for what the people of Northwestern Oregon want,” McCaw said. “Meanwhile, us out here in Eastern Oregon who have no political power — we’re left with the results, which is government and policy we don’t want, we don’t vote for; it doesn’t represent our values at all.”

He reiterated Eager’s point about the population shift turning Oregon more and more blue.

“People want to live around people that share their values and want similar things,” McCaw said. “Oregon is having an influx of people move in that are very left-leaning. At the same time, Oregon has an outflux of people that are very conservative.”

He blamed Bend for the increasing Democrat support in Central Oregon specifically: “It’s known now as a kind of liberal city in Central Oregon, and people self-sort themselves to it.”

At the same time, McCaw said, conservatives are moving from the Portland area and the Willamette Valley seeking conservative community east of the Cascades. But he thinks Republicans still do not have a path to victory in Oregon.

“That’s a population game we can’t win,” McCaw said. “There’s not enough people in Eastern Oregon to outgrow the number of left-leaning people moving into the state. Our only path forward, if we want to have any kind of political say or political power in our own communities, is to separate and join Idaho.”

McCaw said Idaho Gov. Brad Little, a Republican, recently voiced support for the Greater Idaho measure. McCaw also said he hopes to get Idaho’s legislature fully on board with the plan after its state House passed a favorable resolution last year, and to make inroads in Oregon’s legislature, during the upcoming 2025 session.

“Politically, it’s not going to change for the better for conservatives,” McCaw said. “So if you’re a conservative, rural person in Oregon, you need to start considering a new path.”

Logan Washburn is a staff writer covering election integrity. He graduated from Hillsdale College, served as Christopher Rufo’s editorial assistant, and has bylines in The Wall Street Journal, The Tennessean, and The Daily Caller. Logan is originally from Central Oregon but now lives in rural Michigan.