Commentary as GOP primary candidate for governor discusses multifamily issues and whether Oregon’s housing crisis is self-inflicted.
By Aaron Kirk Douglas
With Oregon’s Republican gubernatorial primary days away, candidate Chris Dudley sat down with HFO Investment Real Estate partner Greg Frick for an extended conversation aimed squarely at the multifamily audience: housing supply, permitting timelines, the deteriorating business climate, and the policy choices Dudley argues are driving investment capital out of Oregon.
Dudley, who is a Yale-trained economist, 16-year NBA veteran, certified financial planner, and CEO of a Beaverton-based medical device company, is making his second run for the governor’s office. His 2010 campaign came within roughly 1.5 percentage points of victory, the closest any Republican has come in 70 years. He enters the 2026 primary as one of three leading contenders alongside frontrunner State Sen. Christine Drazan and State Rep. Ed Diehl.
A Diagnosis: Oregon’s ‘Self-Inflicted Wounds’
Asked whether Oregon’s failure to hit Gov. Tina Kotek’s stated target of 36,000 new housing units per year reflects a policy failure or a market problem, Dudley answered “both” — and quickly sharpened the point.
“Just throwing out a target and not really having the specific plan behind it … throws out a mandate that’s not going to be effective,” he said. “Every time the governor has done that — whether it’s on homelessness, education, housing — it’s actually gone the opposite direction.” On housing specifically, Dudley noted that the state isn’t merely missing the target, “we’re not even going to be anywhere near it.”
He framed Oregon’s broader rankings — 50th in fourth-grade reading proficiency, 47th in job creation, 46th as a state in which to do business, and Portland 80th of 81 cities for investment in one widely cited survey — not as bad luck, but as policy outcomes. “These are self-inflicted wounds,” Dudley said. “It does not have to be like this. We live in an incredibly great state. We have great people here. And I believe leadership is about setting the vision, setting the tone.”
Land, Permitting, and the Cost Stack
For multifamily developers, Dudley framed the cost problem in four parts: land, permitting, labor, and materials. State government, he said, has direct influence over two — land availability and permitting timelines.
He stopped short of calling for a wholesale rewrite of Oregon’s land-use system, which he credited with being visionary when enacted more than half a century ago. But he said the urban growth boundary needs to be revisited. “When we’re the fifth least affordable state in the country, it’s something we have to address.” He pointed out that Oregon’s developed urban footprint accounts for roughly 2% of the state’s total land area, leaving room for measured expansion without sacrificing the values that shaped Oregon’s land-use legacy.
Permitting drew his sharpest critique. Dudley relayed an account from a developer in Redmond who told him that approvals, which once took 18 days, now take 18 months. “Anybody who’s built or understands or invested in projects knows that the longer it takes, the more expensive it is,” he said. “If we want to address affordability, we have to streamline that.” If elected, Dudley has pledged statutory limits on permitting timelines.
‘From Business-Unfriendly to Business-Adversarial’
Dudley said his campaign has logged roughly 10,000 miles across all 36 Oregon counties in the past 10 weeks. One theme has been unmistakable across regions, sectors, and political affiliations: Oregon has moved “from business-unfriendly to business-adversarial.”
He recounted a conversation with the owner of one of Oregon’s fastest-growing companies, who hired an outside consultant to evaluate expansion options. “The consultant told him not to do it in Oregon,” Dudley said. The company has since expanded in Texas and Tennessee. The pattern, he argued, repeats across the state: Out-of-state governors personally recruit Oregon employers — offering to meet them at the airport, even take them hunting — while Salem does little to retain or attract investment.
Dudley returned often to a governance lever he believes is overlooked: the power of appointment. Roughly 300 boards, commissions, and agencies receive gubernatorial appointees. “We haven’t had one appointment by a Republican governor [in nearly 40 years],” Dudley said, “and we’ve lost that balance.”
The Vacancy Tax and the Capital Question
The proposed Portland vacancy tax — floated by city councilors and the subject of a recent Portland State University Center for Real Estate survey distributed by HFO — drew Dudley’s most direct warning to the multifamily audience.
“What message does that send?” Dudley asked. “Of course, owners don’t want their buildings to be empty. And now you’re going to penalize them — either for owning a building that’s been hit hard, or for investing in a building you’re trying to lease up. Unless you lower your prices dramatically and take a loss, you’re going to be taxed on it. To me, that’s just crazy. It will scare away capital.”
Frick noted that the policy’s chilling effect doesn’t depend on whether it passes. “Even if it doesn’t pass, just having it out there in the media — if you’re sitting somewhere else, you’re not going to invest,” Frick said. “Outside capital will go other places. And we cannot fix our affordability without it. There’s not enough capital in this state to drive housing on its own.”
Dudley relayed a story from a friend whose family business acquires and repositions commercial properties up and down the West Coast. “He said, ‘I used to love Portland. We’ve looked at four deals in the last two years, and we’ve passed on all of them.'” The discounts on those deals, Dudley said, were 70 to 80 percent. “It’s not about price anymore. He’s not going to invest in Portland or Oregon until he sees a will to change.”
Closing Message
Dudley’s pitch to voters is essentially a turnaround plan: Declare a state of emergency on education, declare Oregon “open for business” on day one, audit agency leadership for alignment with that posture, and reset the regulatory tone toward investment.
“There’s a saying in the investment world that the stock market hates uncertainty,” Dudley said. “Investors and business owners can live with some uncertainty — but they need to understand their risks. Right now, the outside risk of what city and state government might do is the thing keeping capital away.”
The full interview is available on HFO Investment Real Estate’s YouTube channel.
About the author:
Aaron Kirk Douglas is director of market Intelligence for HFO Investment Real Estate in Portland, 2424 SE 11th Ave, Portland, OR 97214.
