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On Jan. 13, Jimmy Crumpacker released a video launching his campaign for the Republican nomination in Oregon's 2nd Congressional District, which encompasses most of the state east of the Cascades.
The video showed Crumpacker, 41, walking across a snow-covered field, carrying a shotgun.
"An avid outdoorsman," text accompanying the video read, "Jimmy is an unabashed conservative and is proudly Pro-Trump, Pro-Life and Pro-Gun."
At 8:29 the next morning, WW has learned, Crumpacker purchased an Oregon hunting license—for the first time ever, according to state records.
His newfound enthusiasm for guns is part of a remarkable transformation from a black-tie fixture of Portland West Hills society to a Carhartt-wearing populist from rural Oregon.
Crumpacker's campaign makes it clear there's a successful model for his makeover: President Donald Trump, another city slicker who rode the grievances of rural America to victory over more politically experienced opponents. In his campaign materials, Crumpacker promises to "defend the Second Amendment, secure the borders and end socialism, once and for all."
Everything about Crumpacker's campaign projects Trump values onto a blank slate—himself—in hopes the 90 percent approval rating the president enjoys among Republican voters nationally will hold true in the 2nd District.
"He's wrapping himself in the Trump flag," says Jim Moore, who teaches political science at Pacific University. "And as a Republican these days, that's what you do."
The Crumpacker family goes back seven generations in Oregon. Jimmy Crumpacker's great-grandfather represented Portland in Congress, so his entry into the race to replace retiring U.S. Rep. Greg Walden (R-Ore.) marks an attempt to follow in a family tradition. But Crumpacker is a newcomer to Walden's sprawling district, which covers most of Oregon but votes reliably red. (Republicans outnumber Democrats 191,000 to 146,000.)
"I asked around but couldn't find anybody who had ever met the man," says Linda Swearingen, a former Deschutes County commissioner and onetime mayor of Sisters. "It seems pretty incredible he would file for a congressional seat in the 2nd District because he hasn't lived here for any length of time."
Crumpacker did not respond to requests for an interview.
Records show he changed the address in his voter registration Dec. 4, 2019, moving from a condo his father owns in Portland's South Waterfront to a farm his parents own in Bend.
Crumpacker has spent most of his life in Portland or on the East Coast. After attending Riverdale School through the eighth grade, he graduated from St. Paul's, a New Hampshire boarding school, and then from Georgetown University in 2002 with a degree in government.
After returning to Portland in 2012, Crumpacker worked at Aequitas Investment Management, a troubled Lake Oswego investment firm that collapsed in 2016, amid federal fraud allegations. That job is not listed in his campaign materials and hasn't previously been reported.
Crumpacker was never accused of wrongdoing related to Aequitas, although a former colleague sued him in Multnomah County Circuit Court in 2014, alleging Crumpacker, after starting his own investment firm, lost a chunk of the man's retirement account trading oil futures. (The case was dismissed.)
Since he came back to Oregon, Crumpacker has demonstrated little interest in politics. His only political campaign contribution came on Feb. 20 of this year—he gave tickets worth $65 to the Deschutes County Republican Central Committee—and, another fact not previously reported, he failed to vote in eight of the past 14 elections.
Crumpacker did serve on the board of the Portland Japanese Garden and as chairman of the board of Oregon Ballet Theatre but left Portland behind for the highest political position an Oregon Republican can reasonably aspire to these days.
By one measure, he's off to a good start. In the most recent quarterly filing period, Crumpacker raised $594,000 ($200,000 was a loan to himself), far outpacing his best-known competitor, former state Rep. Knute Buehler (R-Bend), who reported $386,000. So far, according to Oregon Public Broadcasting, which first reported he'd only recently moved, 98 percent of Crumpacker's donations come from outside the district he hopes to represent.
Former state Sen. Doug Whitsett (R-Klamath Falls) says he's not sure money alone will sway district voters.
"It sounds a little like Michael Bloomberg," Whitsett says. "I would look at where the money is coming from. That's very important. It's been my experience that people in the district are prone to support folks who they know."
Former state Rep. Gene Whisnant (R-Sunriver), now chairman of the Deschutes County GOP, says he saw Crumpacker speak at a recent gathering.
"He's very articulate," Whisnant says, "but I think the other candidates have much more experience and knowledge about the issues in this district."
In addition to Buehler, the race has drawn two other former lawmakers: onetime state Sens. Jason Atkinson (R-Central Point) and Cliff Bentz (R-Ontario).
Crumpacker is betting the political experience of the former elected officials will be a negative. Each of his better-known opponents can be painted as a moderate: Atkinson is a strong environmentalist who has spent the past decade working to save the Klamath basin; Bentz spearheaded the $5.3 billion House Bill 2017, the largest tax increase in Oregon history; and Buehler spent all of 2018 telling voters he was a moderate and bashing President Donald Trump.
So what will make the difference? Elaine Franklin, a political consultant who has run numerous campaigns for Republican candidates and served as chief of staff to her husband, former U.S. Sen. Bob Packwood (R-Ore.), says one force in GOP politics is still stronger than the Trump name.
"In that district," Franklin says, "Oregon Right to Life's role will be a bigger factor than the pro-Trump vote, because they turn out their people."
The anti-abortion group has said whom it doesn't like—it's spending $250,000 to defeat Buehler—but will not bestow its endorsement until next month.