This article was co-published by Street Roots and The Guardian.
When Donald Trump said he was sending the National Guard to Portland to protect immigration officers, local residents immediately responded with characteristic sarcasm. Mocking the president’s portrayal of a city in decline, social media was awash with videos of children in parks, busy farmer’s markets, and September’s falling leaves overlaid with satirical text: “war ravaged.”
When the US Secretary of Homeland Security, Kristi Noem, visited the Immigration and Customs Enforcement building where protesters had been gathering for weeks, she found a small crowd of demonstrators wearing inflatable animal costumes, not a city overrun by antifascist militants. The reality on the ground did not deter Trump from painting the city as unlivable.
“I don’t know what could be worse than Portland,” Trump said in an Oct. 8 White House meeting. “You don’t even have stores anymore. They don’t even put glass up. They put plywood on their windows. Most of the retailers have left.”
Oregon’s largest city boasts a wealth of beauty, nestled between two rivers and surrounded by mountains. It isn’t “bombed-out,” as Trump said, and officials in recent weeks have worked hard to convince Trump the city is not a dystopia, saying years of public messaging about Portland’s challenges are outdated.
“Portland is vibrant and thriving,” said a Sept. 28 letter cosigned by 200 Oregon business leaders, elected officials and organizations. “Just like with public safety, we recognize that there is more work to do and we continue to forge public private partnerships every day to make our city better.”
But Trump’s narrative did not appear suddenly. Portland is, in fact, struggling with a dire affordability crisis, with persistently high rates of homelessness, and too many people living on the streets with mental health and addiction needs.
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Economic leaders in the city have argued for years that those problems, combined with high taxes and racial justice protests, have slowed the city’s economic recovery from a deep pandemic hole.
Progressive critics have said that a period of economic boom followed by the COVID-19 pandemic left the city’s social safety net in disrepair, and their arguments have increasingly resonated with voters in recent years.
Mayor Keith Wilson, a moderate, won election in 2024 in a landslide. But the election also brought four members of the Democratic Socialists of America and an even, progressive-moderate split to the City Council.
Campaigns promising to address root causes of social issues are resonating with voters across the nation, including in New York, where Zohran Mamdani is leading the polls for the mayoral race.
Sameer Kanal, a DSA-affiliated councilor, said like cities across the country, there is a new, relentless focus on affordability.
“How can we make sure that the rent is low enough, not make sure that the people that are richest in the city are benefiting the most,” Kanal said.
Cost of living
In the mid-2010s, national media celebrated Portland’s quirks, bringing an influx of new residents and business opportunities. It also meant housing costs soared and homelessness increased year after year. Average rent in Portland increased by 30% from 2012 to 2015, and the average home sale price grew by nearly 50% from 2011 to 2016. In 2025, Portland’s average fair market rent for a two-bedroom, as defined by the U.S. Department of Housing and Urban Development, was $1,997, up from $905 in 2011.
No single neighborhood’s average rent is affordable to Portlanders making under $31,000 annually. And despite home sale prices decreasing by 7% citywide from 2020 to 2024, high mortgage rates and a low stock of houses for sale leave even median-income Portlanders with few options to buy.
To keep up with demand, Portland’s housing bureau estimates the city needs to build at least 63,000 units affordable for low- and moderate-incomes in the next 20 years.
Mitch Green, a PhD economist and professor elected to City Council this year, said the “Portlandia era” in the 2010s brought significant revenue to the city, but did not create the sufficient affordable housing necessary to meet the needs of the entire population, particularly low-income residents.
“People can, in some sense, adapt a little bit to changes in rent,” Green said. “But when it changes quickly, what you’ll see is, people will fall through the cracks.”
A 2019 project to bring a luxury Ritz Carlton hotel and residences symbolized both the market’s optimism for Portland and its troubles after the economic downturn following COVID-19, people like Green argue.
The $600 million project displaced a block of food carts enjoyed by locals. The city’s tax incentives obligated the project to build affordable housing units or contribute $8 million toward an affordable housing program. When high rents and the arrival of COVID-19 hollowed out downtown Portland in 2020, shuttering the central city after its upswing, the project, like many others of its kind, struggled. Only 8% of the 132 luxury condos sold, and the city may never see the money or the affordable housing after the construction lender foreclosed on the building this summer.
Temporary solutions
The lack of affordable housing has been a key driver in a persistent homelessness emergency. As of July, more than 16,000 people are homeless in Multnomah County. Roughly half are unsheltered, and the vast majority live in Portland.
There are twice as many unsheltered Portlanders as there are shelter units. With affordable housing in short supply, homeless residents are left surviving in the shadows, under constant threat of fines, jail time or sweeps.
The mayor has responded with a dual strategy: clearing encampments, while building out temporary shelter units.
Like in many counties across the West, encampment sweeps have become more frequent and aggressive in recent years. It’s a strategy the mayor says he wants to scale up:
“The City of Portland anticipates returning to enforcement of existing public space regulations on safety, sanitation, and livability in the coming days,” Wilson said. “Every community member, both housed and unhoused, deserves a safe community.”
Meanwhile, the mayor’s office has added 800 beds since January toward his goal to add 1,500 beds by Dec. 1.
The approach is not without its critics. A Street Roots and ProPublica investigation earlier this year found that the increase in sweeps in Multnomah County contributed to a fourfold increase in homeless deaths over a four-year period. And progressive leaders, backed by a throng of local organizers, have argued the city should focus on building permanent housing rather than temporary shelter.
Multnomah County spent $500 million on housing in 2024, with half spent on temporary shelters and navigation services. That approach is expensive and ineffective, according to Green.
“It’s good to open up some shelters so people have a place to hang their head at night, and they don’t have to be stuck out in the winter or the summer experiencing the conditions,” Green said. “But it’s not a solution for homelessness. The solution for homelessness is housing.”
Green and other local leaders recently visited Vienna to learn how social housing might better address Portland’s needs. The European city spends $500 million on its entire social housing program, including all homelessness spending. It is rare for a person to live on the streets.
Meanwhile, the outlook is grim for Oregonians at risk of losing housing. Amid billions in federal cuts to social programs and tax breaks in Trump’s so-called “One Big Beautiful Bill,” the state’s Democratic supermajority legislature cut $100 million in eviction protection funds this year, instead allocating $205 million toward a statewide temporary homeless shelter program.
That’s a heavy loss, according to Becky Straus, managing attorney at the nonprofit Oregon Law Center, which provides pro bono legal assistance for low-income Oregonians.
“We can’t cut our way out of the housing crisis,” Straus said. “Without eviction prevention, more people will end up on the streets and shelters won’t be able to keep up.”
Through August, nearly 8,000 evictions were filed in Multnomah County alone this year, with 90% for nonpayment of rent.
Drug decriminalization
As the city grappled with a sharp increase in homelessness, it also faced the visible impacts of a drug crisis that rose nationally since as early as 2013, following decades of disinvestment in services at the state level. In 2021, Oregon became the first state in the U.S. to decriminalize drugs and allocate hundreds of millions in marijuana tax revenues to build treatment programs across the state. The measure was an attempt to address a persistent addiction crisis, one that appeared more visible with storefront windows boarded up and social services at a minimum post-pandemic. Rather than incarcerating low level drug offenders, the state would invest in building up its crippling support infrastructure.
The decriminalization measure — passed after the city saw 100 consecutive days of racial justice protests — was meant to reduce interactions with the carceral system and confront racial disparities in policing, particularly for low-level offenses, and create a public health framework for addiction. A now-deleted Substance Use and Mental Health Services Administration 2020 survey showed Oregon among states with the least access to substance use and mental health treatment.
But the headwinds the policy faced were fierce. After voters passed the ballot measure, it took over 15 months for the state’s health authority to send funds to new statewide support networks — the other side of the decriminalization coin. That meant people were not arrested for possession or consumption of drugs, even in public spaces. Still, few options existed for a person seeking recovery services for substance use disorders.
In time, multiple studies showed that the impacts of COVID-19, rising housing costs and the arrival of fentanyl coalesced in early 2021, giving rise to the public’s distorted perception that drug decriminalization was responsible for homelessness, crime and high downtown vacancy rates.
Despite appearances, deaths from fentanyl followed an identical trajectory in all 50 states after the drug saturated each market, regardless of each state’s criminal penalties.
“Portland was not an outlier,” former-Multnomah County District Attorney Mike Schmidt said.
Still, the Oregon Legislature ended the state’s decriminalization efforts under public pressure in September 2024, while maintaining funding for new treatment centers.
Portland police have arrested 400 people for drug offenses since then, with 72% charged with misdemeanor possession of a controlled substance. Meanwhile, funding has helped thousands of people access harm reduction, peer support and substance use treatment services through new networks the decriminalization measure created.
Olivia Katbi, co-chair of the Democratic Socialists of America Portland chapter, said she still believes “Portland is the best city in the country,” despite its challenges. “And, Portland as a city has problems in the way that every large American city has problems.”
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This article appears in October 22, 2025.