Portland at a Crossroads: Time to Swing for the Fences

Right now, thinking big is the only option.

The City's Living Room in Another Time.

Every Oregonian knows the story…

There was a time in the 1960s when a vanguard, liberal-minded Republican named Tom McCall won the governor’s seat in Oregon the same year Nixon won the White House.

That was 1968.

What happened next is pure Oregon folklore. McCall and a handful of doers and thinkers set the tone for the most modern chapter of Oregon’s story, as our little state became something of a think tank, and Portland emerged as a model for what medium-sized American cities could become—or so the story went.

And in the next 30 years, we had some big ideas. To name a few: the preservation of public beaches, the nation’s first bottle bill, urban growth boundaries, the reclamation of a freeway to build a park along the Willamette, light rail, Pioneer Courthouse Square, the Pearl District, the tram—all set against the backdrop of a transition from a resource-based timber economy to a high-tech boom that ushered in the state’s most prosperous era.

Of course, Portland and Oregon did not get everything right. Case in point: If you ask generationally rooted communities in North and Northeast Portland how they feel about light rail and bike lanes, you’ll get a very different perspective from the one the city’s public affairs machine has promoted across the world.

Even so, here’s a big takeaway: Portland and Oregon made big decisions in the decades that followed and were generally ahead of the curve—and once in a while, we swung for the fences.

A lot has changed since 1968—the disappearance of liberal-minded Republicans at the top of that list. When McCall became governor, our current mayor, Keith Wilson, was a six-year-old in working-class North Portland, the Vietnam War was raging, Jimi Hendrix was alive and well, and Oregon’s population stood at two million—slightly less than half of what it is today.

Portland Has Changed

It’s no secret that Portland, Oregon, faced more challenges during its pandemic years than just about any other big city in America. But I believe this was precisely because Portland was experiencing serious growing pains as a city right when the pandemic hit. Consider that Portland grew tremendously in the decade leading up to 2020—by 70,000 people in the city and nearly 300,000 in the metro area.

There was also the fact that, before this period, Portland hadn’t really occupied much space in the national or global imagination. But like Seattle in the ‘90s and Austin in the 2000s, Portland was one of a handful of places that defined the 2010s—exporting its culture everywhere, from third-wave coffee to cheffy neighborhood restaurants to DIY everything. Portland, for a time, felt way ahead of just about every place in America.

Today, it’s easy to forget that before the social media revolution of the early 2010s, it was actually pretty hard to know what was happening in places like Portland if you didn’t live there. Just 15 years ago, a Portland story landing in The New York Times or another major outlet was a huge deal—something that would be covered by every local news source and talked about by everyone. Before social media, small cities struggled to break through and sustain relevance—then suddenly, our little city became the hottest thing going, right as Instagram culture took hold.

So while it’s true that Portland changed a lot during this period—so did the world and how we consume our views of the world.

The 2020 Fall Felt Harder

This is the context that matters when examining why Portland seemed to crash so hard in 2020. While it’s true that city, state, and county leadership were famously misaligned, the bigger truth is that the momentum of the 2010s made the fall feel even more dramatic.

To sum it up: We dreamed big, took bold swings, made things happen—and people noticed. But then we got high on our own supply and started reading a steady diet of our own press releases—just as the world was shifting beneath us. And then all was exposed by a massive global crisis.

If there’s one thing I’ve learned in my 25-year career, it’s this: success is a lousy teacher. When everything is going well, you learn very little and start believing the good times will last forever. When things fall apart, you earn a doctorate in life experience.

So what will we do with that education?

Here we are today in 2025, trying to move forward in a world very different from Tom McCall’s nearly 60 years ago. This begs the question—why are we still holding up those years as the golden years? Isn’t it time for the snake to shed its skin?

Here’s where the fun begins. I believe the next couple of years could be the beginning of a golden age—but it’s going to require a combination of recognizing what has worked in the past, using our resources to make big moves, and stopping the habit of spreading ourselves thin. It’s time to swing for the fences.

I don’t have the answers, but here are some critical observations as we write our next chapter.

Fact Number One: Many of Portland’s Best Ideas Came from Ordinary Citizens

Many of the boldest ideas that shaped Portland and Oregon weren’t the result of years of process and feasibility studies. They came from ordinary citizens who banded together to present an alternative vision to entrenched interests and the status quo.

The greatest example? Pioneer Courthouse Square—our celebrated public plaza.

In the 1970s, the site of PCS was a surface-level parking lot, once home to one of Portland’s grandest hotels. Had the status quo prevailed, it would have become a multi-level parking structure at the behest of downtown landlords. In other words, the square wasn’t an inside job—it wasn’t conceived in some backroom at City Hall. In fact, downtown landlords fought it, fearing it would "bring in the riffraff," as a close friend involved in the project reminds me.

Thankfully, entrenched interests lost. And before long, downtown real estate became more valuable than ever. The lesson? Get involved. You might be surprised at how much traction a good idea can gain. And remember—so-called “highest and best use” is always informed by what has worked before.

Sometimes, we need new ideas too.

Fact Number Two: Portland is Actually Well Resourced, Comparatively Speaking

As we speak, the city is attempting to slash $100 million from its $8.27 billion budget. Do you wonder how that compares with other cities?

Here goes.

As cities go, Portland’s budget is on the bigger side of things—$8.27 billion, to be exact. That shakes out to about $12,900 per resident, higher than Seattle’s $11,533 per person on an $8.5 billion budget. Compare that to cities like Milwaukee ($3,290 per resident on a $1.9 billion budget), Austin ($5,620 per resident on a $5.5 billion budget), and Minneapolis ($3,870 per resident on a $1.66 billion budget).

And then there’s the County.

Multnomah County, which includes Portland, is working with a $3.96 billion budget for about 800,000 residents, meaning it’s spending around $4,950 per person. How does that stack up? King County (Seattle) has a $7.9 billion budget for 2.27 million residents ($3,480 per person). Milwaukee County spends $1,490 per resident on a $1.4 billion budget. Travis County (Austin) is even leaner at $1,080 per resident on a $1.4 billion budget. And Hennepin County (Minneapolis) lands at $2,090 per person on a $2.68 billion budget.

And none of this includes Metro—our regional government that spans Multnomah, Washington, and Clackamas counties, which has a budget of about $2.09 billion. Based on my own quick Internet research, I don’t see any comparative organization in these other cities.

Now, let’s be clear—I’m not suggesting we adopt a city service plan that looks anything like Austin’s or Milwaukee’s, nor am I advocating for slashing the city budget. I’m just wondering how we might think about “rearranging the house a bit” in the coming years while we have the generational opportunity to do so. Could we challenge ourselves to take some big swings and learn from our peer cities on how they accomplish major feats with smaller budgets?

Fact Number Three: Portland Spreads Itself Thin and Defaults to Process

Here’s what my experience stewarding a large project through Portland has taught me: we spread ourselves very thin.

There’s a persistent narrative that we’re always short on money, but in reality, Portland dislikes picking winners. Instead, the city distributes resources equally across many small projects rather than making bold investments that could push entire industries forward. While the intent is good, the outcome is lousy.

And then there’s Portland’s obsession with process—a tendency to design the perfect system rather than just stepping up and making a decision for the greater good—like most cities do.

Case in point: As I tried to save Feast Portland from 2020 until finally giving up at the end of 2022, I repeatedly shared the concerns and challenges facing cultural organizations and events in Portland. But I never felt heard, and there was no urgency to help. Instead, I’d get responses like:

• “We need to find a system that helps organizations like yours.”

• “We want to build the infrastructure to save events.”

• And my personal favorite:“We are looking for the next big thing.”

To be honest, I’m relieved I don’t have to run Feast anymore—it was a great project that did everything it needed to do, and I’m glad never had to fade away. However, it was always extremely hard to pull off in Portland. That’s because there are few large companies that can write large sponsorship checks, and most agencies at the city level don’t see advocating for specific projects as part of their role. Here is the irony: Some of those same offices often criticized the number of corporate sponsors we had to bring in and urged us to make the event more approachable in terms of pricing, while failing to support it at a level comparable to similar-sized events in other cities—and in many cases not supporting us at all.

I’m not saying this to complain—I love what we did and am grateful to have done it. I also am grateful to the many organizations that did support us and who continue to support events in Portland.

Portland Is Losing Its Cultural Infrastructure

What I fear is that we haven’t learned from our mistakes. There is still talk of designing the perfect system while the entire ecosystem crumbles.

Consider this:

• Pickathon, one of Portland’s most beloved music festivals, is now leading a capital campaign just to survive.

• Waterfront Blues Festival, another signature event, is cutting its 2025 festival down to two days.

• The Rose Festival, which has been part of Portland’s identity for over a century, is in doubt after suffering losses of more than $1 million in 2024.

These are not the kinds of headlines you see when things are going well and when a good system is in place.

Also, it’s been five years. How is that perfect system coming along?

Yes, it’s true that some of our legacy events could use a refresh. But in a functional city, leadership needs to be a partner in that process and take an active and stewarding role. And while events alone won’t determine Portland’s future, my experience navigating events through Portland’s bureaucracy taught me a lot about how things work here on many levels, and how they might work better.

(There’s also the untold story of how Visit Seattle saved our organization in 2020—but that’s a story for another day.)

The Path Forward

Now is the time to look forward, learn from what we haven’t gotten right, and have the courage to swing for the fences.