I’m looking at new apartments this week here in Portland, Oregon. It’s time for an upgrade.
This has triggered a debate I often have with myself: If I’m going to move, why not leave dysfunctional, far-left Portland altogether?
Had I become so comfortable with the bad vibes of Portland that I would stay here indefinitely, out of inertia or laziness or not wanting to start over?
This is my chance to move to a different city. Or another state. Somewhere with fewer drug addicts and criminals roaming the streets and fewer democratic socialists roaming city hall.
I grew up in Portland. I have lived here off and on throughout my life. During my most productive years as a writer, I lived in bigger, more media-oriented cities, mainly New York and Los Angeles.
But I’ve always loved coming back to Oregon and assumed I would settle here when I retire. Portland always felt like my place. I love the tall trees, the gentle rain, the misty Oregon coast.
Unfortunately, over the last 15 years, Portland has become a hotbed of radicalism and political intolerance. So much so that it has affected my daily life.
I’ve always socialized with creative types. But in Portland, the artistic community is often more hysterical than the violent protesters in the street.
Once it became known I was conservative, I lost about 80% of my writer friends. And maybe half of my other friends. This social exclusion was especially bad during the years around #MeToo, and then COVID, and of course the constant presence of Trump derangement syndrome.
The result is that living here has been like living on a desert island. I feel unwelcome at art events. I avoid literary parties and gallery openings.
One egregious example: I didn’t attend the celebration of life for one of my most important literary mentors, a beloved Portland poet who encouraged me as a young writer and helped advance my career.
I owed so much to this man, and I couldn’t go to his funeral!
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Recently, I saw a TikTok video by a woman whose family had moved from Seattle to Wyoming.
Her message was simple: “No matter how much you think you are aware of the bubble you live in, when you get out of these far-left cities, a whole new world opens up to you.”
This hit me hard. Had I become so comfortable with the bad vibes of Portland that I would stay here indefinitely, out of inertia or laziness or not wanting to start over?
One reason I’m reluctant to move to a red state is I’m not sure I would fit in.
Take for example, Boise, Idaho, the closest red city to Portland. I’ve visited there many times. It’s clean. There are no homeless. The people are super nice. It’s very “churchy” and family-oriented. There’s a large Mormon population.
But could I adapt to such a place? I’ve lived in liberal cities MY ENTIRE LIFE. I have never lived in a place like Boise. Would I find people who understand my sense of humor? People who like the obscure music I listen to? Or read the books I read?
Yes, the people of Boise would share my core values. But would they share my urban tastes?
I had a Republican friend here in Portland who moved to Florida during Trump’s first term. At the time, that seemed like a drastic change.
For a couple of years, I emailed him every few months to ask how he was doing. He had settled right in. Florida was great. He loved it there.
As he grew more comfortable in Florida, I grew less comfortable in Portland. Now, in 2026, moving to Florida 10 years ago seems like a genius move. I am humbled by his foresight.
So what should I do? Be the latecomer, arriving in Tampa or Austin or Nashville a decade after all the smart people already moved there?
I guess it’s never too late. I could still escape.
But what about the tall trees, the gentle rain, and the misty coastline I love so much? What about my roots in the place where I grew up?
Robert E. Lee didn’t abandon his home state of Virginia in the face of a civil war. But Virginia was famous for its proud history and strong cultural heritage.
I’m from Portland, famous for people with orange hair who don’t know what gender they are.
I’ve always assumed Portland’s current political extremism would fade over time. Sooner or later, people would calm down and return to some form of normalcy.
But whenever I try to connect with my former liberal friends, I quickly learn that the derangement is stronger than ever.
So, should I stay or should I go?
These are the decisions we have to make during these difficult times — as we struggle to maintain our sense of ourselves and of where we came from.
I went to meet an old friend for coffee on the East Side of Portland. I don’t make it over to the East Side very often. That’s the more progressive, “social justice” side of town.
That’s where the most WE BELIEVE IN SCIENCE signs are. And Pride flags. And other statements of left-wing beliefs, prominently displayed.
Who in their right mind would wear an actual MAGA hat on the East Side of Portland? You might get attacked by a woman with face tattoos.
It’s also where people get stabbed, shot, and drive their cars into other people’s houses.
I live on the West Side, where people are more reserved and reasonable. Though there’s a lot of SCIENCE and PRIDE over there too.
So I pulled up at the cafe to meet my friend. The sun was out, so people were sitting at outside tables: a lesbian couple, three skinny guys with tattoos, and an odd-looking woman in a dress and lipstick — but also with a tuft of gray hair growing out of the bottom of her chin. I was a bit startled by that.
And then another surprise: When I reached for the cafe’s front door, I saw myself in the glass reflection. I was wearing my bright red Phillies baseball cap.
In case you don’t know, the Phillies are a baseball team from Philadelphia. Their team colors are red and blue. Their hats are red.
I also own a Boston Red Sox hat that is navy blue, a San Diego Padres hat that is brown, and some other hats of other colors. I wear all these hats randomly. I own all these hats because I play softball in the summers and I like to rotate my hats.
The problem with the Phillies hat is that it’s almost the exact same shade of red as a MAGA hat. So if people catch sight of it out of the corner of an eye, they think they have spotted a MAGA person.
For this reason, my Phillies hat has been out of my usual hat rotation. When Biden was president, I wore it occasionally. But with Trump back in office and Portlanders suffering from their various Trump derangement diseases, I do not.
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Earlier that day, I had been wearing the red Phillies hat to run errands near my house. On the West Side, nobody cares what color hat you’re wearing.
But on the East Side, they do care. They care a lot. For instance, the woman with the gray beard had looked up at me as I walked by. She was probably checking my hat. And since it didn’t say MAKE AMERICA GREAT AGAIN, she went back to her coffee.
And really, who in their right mind would wear an actual MAGA hat on the East Side of Portland? Nobody. Especially going to a hipster coffeehouse. You’d be asking for trouble. You might get attacked by a woman with face tattoos.
Seeing the bright red hat in the door’s reflection, I had to make a decision. Go into the leftist cafe with my Phillies cap? Which might draw stares. Which might provoke comments. Or go back to my car and throw it in the trunk?
I mean, at some point, you gotta say enough is enough. A hat is just a hat. Even if it was a MAGA hat, shouldn’t I be allowed to wear it? Isn’t this America?
I did have a MAGA hat back in the early days. This was when I was volunteering for a Republican candidate for governor in 2018. At some point, someone handed out MAGA hats.
Unfortunately, they were so badly made that they were unwearable. The top part of the crown wasn’t stitched properly, so it pointed upward in a clownish way.
Later, I found a real MAGA hat that was immaculate. It looked fantastic. But I never wear it. I keep it under lock and key. It’s my most prized possession.
Meanwhile, back at the cafe, I had to make a decision. Seeing my hat in the door’s reflection, I could clearly see the big white “P” on the front. The “P” stood for “Philadelphia Phillies.” Any idiot could see that.
But leftists are crazy. And they can be dangerous. Especially in Portland. One is wise not to provoke them.
Also, my old friend was probably left-leaning himself. We hadn’t discussed it, but he lived on the East Side with his wife and kids. So even if he wasn’t a Democrat, he would have to pretend he was.
Did I want to put him through the awkward moment of seeing my bright red hat and asking himself, “Why is he wearing that?”
I did not. Nor did I want to get stared at. Nor did I want to have to explain myself. Nor did I want the barista to spit in my coffee. Or worse.
So I went back to my car and threw my Phillies hat in the trunk. Fortunately, my old Los Angeles Dodgers hat was crumpled in the back. I uncrumpled it, put it on, and went back to the cafe.
Now there would be no problems. Though I did get a very suspicious look from the gray-bearded lady.
While President Donald Trump gave the first State of the Union address of his second term on Tuesday night, many Democrats boycotted the speech and opted to engage in some unconventional counterprogramming.
For example, some Democrats attended an event organized by Defiance.org at the National Press Club in Washington, D.C, and at least one of them was joined on stage by some ... special guests.
'Tonight I defy Trump and his authoritarian project by standing in joyful, radical, peaceful resistance with the Portland Frog Brigade!'
Video emerged on Tuesday night showing Oregon Rep. Maxine Dexter (D) speaking at the event, while six inflatable frogs stood beside her and many more stood off to the side.
"Tonight I defy Trump and his authoritarian project by standing in joyful, radical, peaceful resistance with the Portland Frog Brigade!" Dexter said as the frogs jumped around and waved small American flags.
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Defiance.org describes itself as a "club for courageous Americans — people willing to take peaceful, lawful, defiant action to defend democracy from a wannabe dictator." The organization partnered with the Portland Frog Brigade for this event, though the group has been making its anti-Immigration and Customs Enforcement stance known since last year.
According to its "about" page, the Portland Frog Brigade was created after an anti-ICE activist — apparently known by several names such as Toad, Toad Todd, and antifascistfrog — was sprayed by federal law enforcement outside Portland's ICE facility. The organization emphasizes that the "absurdity" is core to the idea behind the group:
The image of a cartoon frog facing off against a wall of heavily armored men was so strikingly absurd that it cut straight through the noise and brought home the reality that our government is treating peaceful citizens as enemies.
From that moment, the frog became a symbol of resistance that refuses to lose its joy. The Brigade took inspiration from Toad and grew as so many others donned inflatable animal suits and joined actions across the country and around the world.
However, not all is well in inflatable paradise.
The partnership between Defiance.org and Portland Frog Brigade has apparently caused infighting with an adjacent group called Operation Inflation.
Operation Inflation posted a video on Instagram criticizing the partnership and distancing itself from the other organization: "The frog brigade, however, saw the frog and emptied it of context, taking the image without the work, the aesthetic without the politics, and shared it with an establishment that can only function through neutralizing resistance."
"When the loudest voices take the safest route, do not trust them," the spokesperson in a red frog suit said.
Toad, the figurehead, reposted the video on his own Instagram account, seemingly attempting to likewise distance the symbol from the Portland Frog Brigade. He has also previously called the brigade a "business of grifters seeking to piggy off the backs of actual activists."
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I know this guy, Richard. He’s friends with a couple of different friends of mine. He’s in his late 40s. He’s had a successful microbrewery business going for many years.
Last year, I heard that his business was in trouble. And then, more recently, his wife filed for divorce. He is apparently having problems seeing his kids.
Maybe this is our new male initiation ritual. Getting crushed by family court. Losing your business to far-left politics. Being abandoned in your moment of need.
I saw him recently at a large gathering. He was in pretty bad shape. He was getting screwed at family court. He was blaming Trump for his business problems.
His blaming Trump was no surprise. Many otherwise intelligent people do that automatically here in Portland. Everything is Trump’s fault. I don’t really hold it against them. The propaganda is so thick here. And if you own a public-facing business, you probably have to go with the flow.
More likely, the true cause of his business problems is the economics of Portland. Taxes are up. Insurance is skyrocketing. Homeless people have invaded your neighborhood. Drug addicts are lighting your dumpster on fire.
So I was at this event, and I ended up in a small group with Richard and a couple of other guys. I could see that he was upset. He looked terrible.
I could relate to his situation. I had gone through a similar compound disaster when my father died, right in the middle of my own divorce.
So I had felt that pain. But I didn’t have kids. Which probably makes Richard’s situation much worse.
Eventually, the other guys wandered off, and I found myself giving Richard a little pep talk. I told him what happened to me and explained how at the time, I tried to think of it as a test.
I thought to myself: How often in life will I have to face two life-changing crises, coming from two different directions, at the same time?
I tried to think of my situation as a challenge, a rare opportunity to test my mettle, as I faced a mountain of emotional stressors and practical problems.
I couldn’t tell if he was buying it. And I didn’t know him that well. So I left it at that.
But in the days after, I thought more about Richard’s situation.
He was a solidly upper-middle-class guy. His parents were well off. He went to a good college. He was a successful businessman and a respected member of the local microbrew scene. His brewery had prospered for years, before Portland took its current downturn.
He had really had an easy time of it, all things considered. So really, my idea that this was a “rare opportunity” was not far off. His current problems were easily the worst thing that ever happened to him. And they were all happening at once!
This also might have been a good time to try to red-pill him on local politics. Bro, Trump isn’t the reason you can’t run a business in Portland. But he wasn’t going to change on that.
But the “test” thing. That was still a valid point. Richard had never been hit this hard. And like a lot of men, he wasn’t ready for it. He had lived a relatively soft life.
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People have been saying for years that part of the problem with American men is they don’t have any form of initiation ritual.
There’s no rigorous coming-of-age process. We have no “rites of passage.”
You can live your whole life and never have to endure any true hardship or serious deprivation.
Other cultures make a point of creating those “rites of passage.” Growing up in the West, I heard about young Native American men going on “vision quests.” They ventured into the wilderness by themselves, with no food and no protection from the elements or predatory animals.
In this way, they proved themselves worthy of their people, both physically and mentally. They were pushed to the limits of their endurance.
This was not only a physical ordeal, but a chance for spiritual growth as well. Becoming a man was not just about strength and skill; it was about humility and understanding your responsibilities within your tribe.
Once you had experienced the difficulties of fending for yourself, you would forever appreciate the security of life within a stable and healthy community.
I thought about Richard’s predicament, which is now fairly common in America. What was happening to him was happening to men all the time.
Maybe this is our new male initiation ritual. Getting crushed by family court. Losing your business to far-left politics. Being abandoned in your moment of need by your own social class, because they’re progressive Democrats as well.
That’s how I would think of it if I were him. What else are you going to do? Cry to your lawyer? Complain about Trump? Whine to your Kamala-voting buddies?
Or are you going to grieve your losses, accept your situation, and then respond with a new resolve, a new clarity of mind, and perhaps a stiffer spine?
I mean, I feel for the guy. He’s going through hell. But these kinds of men have got to stop crying and focus on what is really going on around them.
Think of your present difficulties as the rite of passage you should have experienced when you were 14. Think of them as your overdue vision quest. You’re in the wilderness now. You have only yourself to depend on.
My first experience with an activist journalist came in 2019. I had traveled to Oregon’s state capitol in support of a small group of Republican state legislators. They had refused to appear for a vote, to prevent the Democrats from passing a hotly contested education bill.
This was a strategy the Republicans had used before. Oregon is a solid blue, Democrat-run state. Often, the only tool the Republicans had to stop a bad bill was to leave town and thus deny the legislature their quorum (the necessary number of legislators needed to vote).
Did she really hate Republicans so much, she couldn’t contain her rage for the 10 seconds she was required to listen to my answer? She was a professional news reporter.
So that’s what they did. The Democrats were up to their usual money-wasting, ideology-pushing ways. So the Republicans went AWOL.
Our busload of Republican volunteers — about 20 of us — unloaded at the state capitol.
There was media everywhere. The day before, the Democrats had threatened to send the state police after the rogue legislators and drag them back to the capitol building.
To this, one of our more salty, cowboy hat-wearing legislators responded: “Send bachelors and come heavily armed.”
This was about as colorful as politics got here in Oregon.
So that’s why we were there. To show the public that those renegade Republicans had the support of their constituents.
We’d been told to look presentable and interact with the media if possible. I was wearing glasses, a sweater, and a button-down shirt. I looked like a school teacher or maybe a writer (which I am) or one of those retirees who volunteers for things (which I also am).
We gathered in the crowded capitol building. There were reporters and camera crews scattered throughout. I felt like I should break the ice and go talk to one.
I spotted a TV crew from the Portland Fox affiliate. The reporter was dressed up, hair and makeup camera-ready. She was probably 45 years old. She appeared to be a seasoned, professional reporter.
So I walked over to her and said: “Do you guys need to interview a Republican? Do you want a quote?”
“Yeah, sure,” she answered.
At this point, I was still very new to politics. To me, it still seemed like a game. Like a friendly competition. But that’s what I liked about it. I enjoyed being part of a team and engaging in spirited debate with the other team.
But I also believed in fair play and maintaining a sense of humor. That was my take on the present situation. It was funny. The outlaw Republican cowboys versus the non-binary, they/them Democratic elites? This was a great story!
Which was why it was getting so much attention. And why the capitol was packed with people. Even the national news was covering it.
The cameraman lifted his camera onto his shoulder. I straightened my sweater and brushed my hair back with my hand.
The reporter asked if I was ready, and I nodded. They turned on the camera.
In her professional voice, the reporter asked me if the Republicans’ leaving town was the proper way to debate an education bill.
She pointed the microphone at me, and I answered, “They’re totally outnumbered. But most people agree with them. So I do think it’s an appropriate strategy.” Or something like that.
That was it. A couple sentences. Clean and simple. She was going to need a quote from someone on the Republican side, so I gave her one.
Not only that, I knew to look at her and not the camera as I spoke. To actually listen to her question before I answered. So it would look good on TV.
But that was the problem. When I looked into her face, she was glaring at me. She had this look in her eyes. It was a look I was not prepared for. I’m not sure I’ve ever actually seen someone look at me like that.
It was a look of total hatred. Like burning, seething hatred. And it was leveled at me! And I was being cheerful and nice. I was helping her out!
That look on her face was disturbing. Once they turned the camera off, I just walked away.
What was this woman’s problem? Did she really hate Republicans so much, she couldn’t contain her rage for the 10 seconds she was required to listen to my answer? She was a professional news reporter. She was 45 years old!
If it were some 22-year-old who just graduated from “activist” journalism school, I could understand. But this was a grown woman. Had she never done this before?
Hey, lady: You’re not supposed to HATE people for having an opposing opinion. I DID YOU A FAVOR!
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So now, several years have passed, and I see this same phenomenon almost every night on my local news. Not necessarily seething hatred. But something similar. Specifically: the constant messaging that any conservative position, on any issue, is — of course — totally evil. And that the left is always morally correct.
That’s what I saw in the eyes of that local Fox reporter. A total lack of perspective. A soulless fanaticism. She was like a “hate robot” with one mission: the annihilation of people like me!
Unfortunately, this behavior is commonplace now. The division continues to get worse. I don’t know what the solution is, except to point out that hating people, at this intensity level, can’t be good for your health. If you’re hating and seething, you’re probably hurting yourself more than anyone else.
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