Once upon a time, Portland was a quirky, endearing city with much to recommend it.

“Keep Portland Weird” became a local mantra to encompass the city’s eccentricity (even though the phrase originated in Austin, Texas). The television comedy “Portlandia,” starring Fred Armisen and Carrie Brownstein, affectionately parodied the city’s idiosyncrasies and ran for eight seasons. It was where young people went to retire, or so a joke went.

Nothing such as this would be applied to Cincinnati or Charlotte, N.C.

At the same time, the Rose City or PDX, take your pick, was also a beautiful urbanist’s dream. It offered a real downtown, walkable neighborhoods including the Alphabet and Pearl districts, and abundant rail transit, along with Amtrak service at the stately Portland Union Station. The depot was opened in 1896 and restored a century later.

This was a city that cared about itself, going back decades. For example, a freeway that would have been rammed through Portland neighborhoods sparked a revolt in the 1970s. It was canceled. Instead, funding was directed to light rail. No wonder several of my friends from Phoenix moved to PDX.

That once upon a time was not so long ago. Indeed, it ran up through the 2010s.

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Lately, Portland is known for rampant homelessness, drug addiction and crime. Portland’s civil unrest after the 2020 murder of George Floyd by a Minneapolis police officer made Seattle’s troubles tame by comparison.

Late in July, The New York Times delved into the problem, summing it up this way:

“This city of 635,000, home to the world’s largest bookstore and majestic views of snowcapped Mount Hood, has long grappled with homelessness. But during the pandemic this perennial problem turned into an especially desperate and sometimes deadly crisis that is dividing Portland over how to fix it.”

The split is between compassion and open arms and citizens affected by crime, garbage and encampments overflowing into sidewalks and neighborhoods. Meanwhile, decriminalization of drugs for “personal use” — including fentanyl and methamphetamine — has further riven Portland. Sound familiar?

New York Times columnist Bret Stephens, an anti-Trump conservative, called the measure “a public policy fiasco.”

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One friend who moved from Phoenix to Portland told me, “Ten years ago, Portland was an urban success story virtually without parallel in America. Today, it looks like the road to the landfill and, in some areas, the landfill itself. We did this to ourselves from equal parts denial and sentimentality. Our preoccupation with grand abstractions such as ‘social justice’ midwifed a crisis that will take years to resolve. 

“How do you love a city that can no longer afford to pick up the trash in its streets yet taxes its citizenry at extortionate rates?”

Was this always Portland’s destiny?

In 1900, it was still the largest city in the Pacific Northwest. Portland — which was almost called Boston, the name being settled by a coin toss — offered the largest inland port on the West Coast, along with large manufacturing, timber and railroad operations.

But by 1910, Seattle had overtaken Portland to become the most populous city in the region — and never looked back.

This was a very different Seattle, too. It was a business city on the make, with “Bill Luck” — William Boeing and Bill Gates with Microsoft. Although one business executive commented that Gates knew more about the other Washington than his home state, Microsoft’s co-founder Paul Allen became a model civic steward for Seattle until his untimely death in 2018.

With a natural deep-water port and then the rise of Amazon, major corporate headquarters clustered in the Seattle metropolitan area.

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In the Milken Institute’s 2023 Best Performing Cities report, metro Portland’s overall rank was No. 67. Seattle-Tacoma-Bellevue ranked No. 34. The rankings covered 200 large metropolitan areas.

According to the Brookings Institution’s Metro Monitor, which looks at economic performance based on growth, prosperity, overall inclusion, racial inclusion and geographic inclusion, Portland clocked in at more than a 16% increase in jobs between 2011 and 2021. Portland’s gross metropolitan product grew by 31% over the same period.

By contrast, metro Seattle saw a 19% increase in jobs and 59% growth in gross metropolitan product.

Portland had Nike, Oregon’s only Fortune 500 company, but it was headquartered in suburban Beaverton. By contrast, Allen created an “innovation district” in South Lake Union, anchored by Amazon and 50,000 well-paid jobs as well as offices and laboratories for tech firms and biomedical outfits. Starbucks’ headquarters is just south of downtown.

Seattle attracted high-end outposts of every major Silicon Valley company because of a talented workforce, the University of Washington and lower cost of living. Especially before the pandemic, startups flourished here.

Portland’s “Silicon Forest,” with Intel semiconductor plants and Portland State University, pale in comparison.

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Perhaps because of its troubles, Portland’s population declined by nearly 3% from Jan. 1, 2020, to July 2020, according to the Census Bureau. Seattle added 1.7% more people.

But as my colleague Gene Balk recently pointed out, 7.2% of adults in metro Seattle felt pressure to move from their neighborhoods because of crime, the highest percentage among major U.S. metropolitan areas.

Maybe this offers a cautionary tale to Seattle, Portland’s big brother to the north on the Amtrak Cascades line and Interstate 5. Maybe the two cities are in the same dilemmas.

The new Seattle City Council looks to be unsettling like the old one, albeit without Kshama Sawant. For example, Andrew Lewis, who was initially in favor of defunding the police only to walk it back and voted against prosecuting public drug use and possession, won the most primary votes in his district.

This promises to complicate Mayor Bruce Harrell’s plans to fight crime, “reactivate” downtown — and avoid the fate of Portland.