Bynum, a Democratic state representative since 2017, is challenging freshman Rep. Lori Chavez-DeRemer (R-OR) in a congressional district spanning the southern Portland suburbs and central Oregon. House Democrats only need to gain four seats to win a majority in the chamber, and this one is at the top of their list.

Voters in the area have seen the names of both candidates on the same ballot before, which is where Bynum’s past political success comes in.

Bynum twice beat Chavez-DeRemer for a seat in the state House of Representatives, first in a 2016 open-seat contest for a district entirely within Clackamas County, south of Portland, and in a 2018 rematch toward the end of Chavez-DeRemer’s 2011-2019 tenure as mayor of Happy Valley, a Portland suburb where about 24,000 people live.

Chavez-DeRemer wasn’t deterred by the losses from seeking higher office. Her chance for a U.S. House seat came in 2022 when centrist Democratic incumbent Kurt Schrader lost in the primary in the newly redrawn district to a far-left challenger, Jamie McLeod-Skinner. Then, in the general election, Chavez-DeRemer presented herself as a relative centrist in a district that Joe Biden would have won in 2020 over his ousted Republican rival, then-President Donald Trump, 53.2% to 44.4%.

In the open-seat House race, Chavez-DeRemer beat McLeod-Skinner 50.91% to 48.83%. Oregon’s 5th Congressional District was among only 18 out of 435 nationally held by a Republican that also would have backed Biden. Eight districts went the other way in that they would have backed Trump but also elected a Democratic House member.

House Democrats, not surprisingly, are eager to flip the district.

“While competitive on paper, Democrats have the structural advantages,” Oregon political analyst John Horvick said in an interview.

Moreover, some of the anger from the 2022 elections about Portland-area homelessness and civil unrest has subsided, at least somewhat.

“They’re still big issues, but not quite as intense as they were, and the economy is going better for a lot of people,” said Horvick, senior vice president at Portland-based DHM Research, a public affairs firm.

Campaign likely to be won in the middle

Bynum would be the first black person elected to Congress from Oregon. That’s notable in a state with a fraught history on race. When Oregon became a state in 1859, its constitution included a provision that barred black people from moving there. Another provision precluded black ownership of real estate. It took until 1959 for Oregon to ratify the post-Civil War 15th Amendment, which guaranteed citizens’ right to vote, regardless of race.

Today, Oregon is known more as a progressive haven, at least in Portland. There, locals claim it stands for social justice, empathy, and tolerance. Yet the congressional district Bynum is seeking to represent is much more centrist.

She’s trying to win in a sprawling district that is a three-plus-hour drive from its northern part, in the southern Portland suburbs, south to the central Oregon community of Bend, with a population of just over 100,000 people. The landscape in between yields a fairly diverse set of voters, said Jim Moore, a political science professor at Pacific University in Forest Grove, Oregon.

“You’ve got mountain bikers and loggers and colleges and lots more,” Moore said in an interview.

Chavez-DeRemer could have a tough reelection because she isn’t running against the 2022 Democratic nominee, McLeod-Skinner, Moore said. McLeod-Skinner is widely considered to have only mediocre campaign skills and limited personal appeal.

The first-term congresswoman won “against someone seen as a progressive Democrat. Two years later, Janelle Byrum is running as a moderate Democrat,” Moore said.

Chavez-DeRemer is also aiming to capture centrist voters’ support. She’s among more than 30 House members, including a half-dozen Republicans, who have signed a bipartisan pledge to uphold the results of the 2024 election amid an increased focus on Congress’s role in certifying the tally next January. The other five Republicans also are in tough reelection races, to varying degrees: Reps. Don Bacon (R-NE), Brian Fitzpatrick (R-PA), Mike Lawler (R-NY), Nick LaLota (R-NY) and Anthony D’Esposito (R-NY).

None of the six Republicans who signed the pledge voted against certifying the 2020 election on Jan. 6, 2021. Several of them were not yet in office, including Chavez-DeRemer. In total, 139 House Republicans voted against certifying President Joe Biden’s victory.

Chavez-DeRemer “has done an effective job of communicating around issues her district cares about, without stepping out of line with House Republicans,” said Horvick, the Oregon political analyst. “She doesn’t take strident positions on issues of the day. She’s trying to position herself as workaday, constituent services-oriented without getting caught up with the craziness of D.C.”

Trump continues to insist that he did not lose the election in 2020 — stoking fear that he may again encourage his supporters to block certification of the election next January if he loses for a second time.

In the final weeks of the campaign for Oregon’s 5^th Congressional District, Democrats and allied outside liberal groups are trying to tie Chavez-DeRemer to Trump and, sometimes, travel companion Laura Loomer, a conspiracy theorist who has posted racist X remarks about Vice President Kamala Harris and is a longtime 9/11 truther. Even before the Loomer controversy arose, Bynum’s campaign ads repeatedly used the phrase “MAGA” to describe Chavez-DeRemer.

Bynum also emphasized abortion rights at a time when Democrats think the issue can help them politically after the 2022 Supreme Court Dobbs v. Jackson Women’s Health Organization decision, which made the procedure a state matter to decide rather than a national right.

“The Democrats are trying to change the conversation from progressive vs. right wing to, ‘They are the extremists,’” Moore said. “There seems to be about 20% who haven’t made up their minds. That says people don’t know who the candidates are yet.”

Turnout is key

During a recent Sunday afternoon on a sunny patio at Starbucks in Happy Valley, Greg Thompson, 44, a civil engineer in the Portland area, said he couldn’t readily identify either the name of the sitting Republican congresswoman, Chavez-DeRemer, or her Democratic challenger, Bynum. But having twice voted against Trump, Thompson said he plans to do so a third time, adding that he would back the Democratic congressional candidate once he brushes up on Nov. 5 ballot offerings.

“Trump never should have been anywhere near the White House,” Thompson said. “It’s frightening he could return.”

Yet another coffeehouse patron, Megan Higgins, 34, who said she works in the natural gas industry, plans to back Trump for president and Chavez-DeRemer in the House race.

“The economy was good when he was in office,” Higgins said. As for Harris, “She’s going to raise taxes, whether she says so right now or not.”

At the presidential level, Oregon is expected to go Democratic easily. No Republican nominee has won it since President Ronald Reagan’s 1984 reelection romp. In 2020, Biden easily beat Trump in Oregon, about 56% to 40%.

The Oregonian newspaper recently endorsed Bynum.

“As the state representative for the Happy Valley area since 2017, Bynum, 49, has developed a reputation as an effective, business-minded legislator, drawing from both her engineering background and co-ownership of four McDonald’s restaurants,” the Oregonian’s opinion editors wrote. “She chaired the House Committee on Economic Development, leading bipartisan passage of the critical Oregon CHIPS bill, which provides funds for semiconductor companies’ expansion and creates a process to designate some land for industrial development.”

As for the Republican incumbent, “Lori Chavez-DeRemer, 56, has frequently highlighted actions that she said show her bipartisanship in representing the district,” the editors wrote. But her House voting record is more conservative.

“While Chavez-DeRemer said she would not support a federal ban on abortions, she has previously declared her support for banning abortion after about six weeks, giving Oregonians good reason to question her commitment,” the editors wrote in the endorsement of her Democratic opponent.

Of course, newspaper endorsements don’t decide elections. And House incumbents are tough to beat under any circumstances.

Plus, Bynum’s two prior wins for that state House seat don’t guarantee success in a congressional race. A vivid example came three decades ago in a two-hour flight south from Portland International Airport. In early 1994, Democrat Adam Schiff had recently left his position as a federal prosecutor and was running for a suburban Los Angeles state Assembly seat. He lost that race — and a subsequent one in November for a full, two-year term, to Republican Assemblyman James Rogan.

But Schiff rebounded politically and won a state Senate seat in 1996. Then, in 2000, he challenged and easily beat Rogan for a U.S. House seat covering much of the same Southern California terrain, reversing his twin losses to the same opponent six years earlier. Schiff, in the latter third of his 24-year House career, became a leading critic and investigator of the Trump administration. He parlayed that into a successful 2024 U.S. Senate candidacy — he’s on the cusp of winning an open seat in California on Nov. 5.

Like most close races, Oregon’s 5th Congressional District result will likely be decided on turnout, though the phrase has a different meaning in the state, which has long conducted its elections entirely by mail. So, Nov. 5 will show whether, at least in this stretch of north-central Oregon, past political performance does predict future outcomes.