In Portland, The Lunatics are Always at the Gates

Musings from a city in throws of an existential fog

About a week ago, I received a text from my writing and drinking buddy, Richard Cheverton (of Portland Dissent fame):

“Finally got the bill for the pleasure of living in Portland. I hate this fucking town.”

Richard’s car, which he bought less than a year ago, had been broken into while parked along the Montavilla Strip. The thieves made off with “an old gym bag full of dirty laundry and a lock they will never open.”

The PDX Real team had a similar experience 2 years ago while dining with friends in Sellwood. A witness—who, coincidentally, was a 5-star PDX Real follower—saw a car pull up in front of ours. Two men jumped out, smashed our passenger-side window, and stole a bag full of beach towels. The witness tried to find someone to call the police and ran into us (“Hey, it’s Angela!”), informing us about the break-in of a white Mercedes just down the street. We immediately knew it was our car. I ran over and found a couple of shop owners who had also witnessed the smash-and-grab.

We didn’t even call the police. There was no point. They undoubtedly wouldn’t have come. Instead, we took photos, gathered witness information, and had the window replaced a few days later. We were out the deductible, but our insurance company eventually reimbursed us.

The real point is this: both Richard’s and our experiences are part of Portland’s decline into a postmodern urban abyss. It’s all so completely, mind-numbingly pointless. The thieves created the maximum amount of destruction for the minimum reward. What would someone even do with a bag full of dirty laundry or towels? (Every time I picture this, I hear Walter Sobchak yelling, “The whites!”)

The next evening, as Richard and I plotted our escape from Portland over bourbon at Tinker Tavern, he leaned in and said, “I don’t think I’ve ever despised a city I’ve lived in this much—and I lived in Detroit!”

Richard has lived in nearly every major U.S. city—Chicago, Philly (his favorite), Cleveland, Detroit, LA, and Seattle—before landing in Portland. I’ve traveled to nearly 40 countries and most of America. Nowhere else compares to Portland today, and that’s not a good thing.

Here's a list of cities I've been visited in the last seven years that weren't as bad as Portland:

Hong Kong * Phnom Penh, Siem Reap, Sihanoukville – Cambodia * Fes, Tangiers – Morocco

Dublin, Galway – Ireland * Barcelona, Madrid – Spain * Amsterdam

Bruges, Antwerp -Belgium * Krakow, Poland * Split, Croatia * Prague, Brno - Czechia

Budapest * Bratislava, Slovakia * Athens, 4 Greek Islands * Seattle * San Diego * Las Vegas

Salt Lake City * Indianapolis * Nashville * Louisville * Greenville, NC * New Orleans

St. Petersburg, Orlando, Tampa, West Palm Beach, Key West – Florida * New York City

Chicago * Boise

The only cities that even compete with Portland's homeless problems are Seattle, Athens, and Budapest. Athens has always been notoriously bad for addiction, walking zombies and graffiti, but there are no tents. Budapest is bad, but also, there are no tents, and the only reason they currently have homeless, according to locals, is because they elected a socialist mayor, Gergely Karácsony. Before the new mayor was elected in 2019, it was illegal to be homeless in the city, so the cops simply took them to shelters every night. Morocco, especially Fes, was frightening on a whole other level, particularly since I was traveling with a red-headed woman. They don't see many of those in Morocco.

It’s not just the crime and homelessness that make Portland’s decline so brutal. It’s the fact that it was orchestrated by smug left-wing politicians who lacked the experience or rationality to maintain the city’s once promising trajectory—one originally set by leaders like Bud Clark and Vera Katz. Portland had it all: world-class food, art, and music; some of the safest streets in the country; and a thriving economy.

So what happened? How do you screw that up in less than a decade?

Angela and I began speaking out nearly ten years ago after buying a home in the Mt. Tabor neighborhood. Many blame Portland’s downfall on the Covid Crisis Psy-op, but the city’s decline began in earnest around 2015. A friend of mine who owned a furniture store in the Alphabet District complained to me about the homeless population near his shop. I was skeptical at first—Portland has always had a homeless presence - but he described an alarming shift: these weren’t the usual down-on-their-luck individuals quietly surviving by panhandling; these new homeless were aggressive, confrontational, and intimidating. It was a harbinger of what was to come.

Angela and I started PDX Real to help. We had spent years learning how the government worked—and why it was failing. We hoped that by sharing the truth through a platform, people could make informed decisions about who to vote for and which policies to support while holding politicians accountable for questionable legislation.

At first, it worked. Within a year, we had over 100k followers; in two years, 200k. Our content averaged 7 to 10 million views per month. Angela, the face of PDX Real, became a local celebrity. Strangers would approach her in public to say hello or thank her. Some had stars in their eyes, summoning the courage to introduce themselves. I’ve seen people cry while speaking to Angela, believing she was a savior of sorts. I’ve also seen a biker dude tell her he “jerked off” to her videos. Such is the price of fame.

PDX Real achieved real political victories. We helped elect Rene Gonzalez, Nathan Vasquez, and Julia Brim-Edwards. We’ve had numerous politicians in our home, including Betsy Johnson, Ed Diehl, Will Lathrop, Gonzalez, Vasquez, Brim-Edwards and, incredibly, JoAnne Hardesty (who once told a group of neighbors that we didn’t need police because they “just hang out at donut shops all day”). Nathan Vasquez made us one of his first calls when he decided to run for Multnomah County DA. We’ve also met with powerful political operatives and some of Portland’s wealthiest, most influential individuals. We’ve been deeply plugged in for years—some of these people, we now call friends. We honestly have the best Rolodex in the city.

Our follower base include all walks of life: public employees, whistleblowers, everyday working class Oregonians, retail and restaurant owners, people experiencing homelessness, the disabled, the young, the old, the disenfranchised and the skeptical.

PDX Real broke major stories before mainstream outlets did—often, they copied our content without giving our platform credit. We had thousands of followers who worked in every industry and openly share with us what they saw. The legacy media feared us: real journalism without the need to conform.

Of course, making waves also makes enemies. At first, it was the usual suspects: leftists, communists, and anarchists who branded us fascist, racist, or whatever -ism or -phobia was trending at the time. Before we fully learned the rules of the new road, we would sometimes get into online battles, to our detriment. Social media is a paradox—you engage not to convince your opponent but to sway silent onlookers. Still, at times, it felt like trying to use the Lydian Chromatic Concept to solo over “Giant Steps” when George Russell might as well just scream, “Play whatever the fuck you want!”

I apologize for the random musical shibboleth, but it is the only way for me to truly describe the complexities of social media engagement.

Our enemies weren’t just on the left. The far right, and even centrists, attacked us—often out of pure petty jealousy. They dredged up my past from 25 years ago as an excuse to discredit us, but the truth was, they wished they could be Angela, but simply don’t have the panache. They lacked her talent, intelligence, creativity and drive. Some were bored wine moms cosplaying as booze-swilling trad wives; others were left-leaning professionals looking for meaning in their bored existences and had given over to the temptation and power of what it meant to be online, mean, and unprincipled.

One such person—a podcaster who refused even to be introduced to us—called Angela an anti-Semite because she once mispronounced a Jewish name (sorry, its not Ellen Rosen-blum, its Rosen-bloom). Ironically, the far left regularly calls us “genocide supporters” for our measured support of Israel. The horseshoe theory is real: the far left and far right are one and the same entity. James Lindsay often discusses the new “Woke Right” on his X account and on his Substack. These individuals act exactly the same way the Woke Left acts, they are just have diametrically opposite views.

We have accepted this is part of the fallout of reporting the inconvenient truths in this city for millions of viewers a month. We’ve had plenty of people delcare they would take us down. It’s never happened because we never took them seriously. After all, we were not doing this for fame, but rather, to return Portland back to what it had been. Maybe it’s because I’ve spent time around actual criminals who might actually kill you, these threats rang hollow and impotent. Or maybe it’s just because Angela is rarely fazed by such malevolence. And after all, these takedown missions were always crafted in such a way that others could expand their own readership and views.

One particularly amusing antagonist is Kimberley Hanks-McGair, a lawyer and amateur shit-poster. She despises Trump and Elon Musk, yet loathes woke gender theory idealists.

Now, I’ve blocked McGair on X previously. She uses the usual online tactics of extreme anger, mocking attitude, and sea-lioning. In other words, she is extremely loathsome and exhausting on social media. I don’t remember why I blocked her over a year ago. Undoubtedly, she decided rather than engaging in an interesting debate on the merits of her opinions, she reduced herself to ad hominem in an attempt “to win.” Recently, she came onto my thread again because her former X account had been suspended. Now, I don’t know exactly what one has to do in order to get an account suspended on X these days, considering that nearly half the content on the platform currently is Jew-hatred and Holocaust denial, but I’m guessing that it has be substantial. Of course, McGair used the classic Joy Reid excuse that her account “got hacked” and then blamed the Hitler-du-jour Elon Musk for it. Not kidding:

Last week, I reposted a Governor Kotek repost of an article about how Portland supposedly is “back on track.” This article was a Bloomberg article from a journalist who supposedly resides in Portland (interesting enough, the byline on this article has since been removed by Bloomberg, perhaps because of the backlash). Now, the article was written from the perspective of someone who is trying to explain Portland to an audience who doesn’t live anywhere near the city and has a general fascination of the recent history of the city. The article, entitled “Progressive Portland Plots a Comeback,” went into the history of Portland being a mecca for young people who loved to bike to work, scarf down cart food, and indulge in their various strange shades of weirdness. In other words, this article could have been written by AI, and since the byline has disappeared, I’m truly wondering if it was! Also, the individuals the writer interviewed are the usual progressives and activists who either have no real idea how this city works, or are so bought into the activist mentality that they intentionally obfuscate this reality.

As of this date, Kotek’s repost has received 140K views. The post has received 87 likes and nearly one thousand comments, nearly all of them either disagreeing with her or outright mocking her. My rather innocuous comment on my repost simply questioned whether people really believed what Kotek was claiming. It was more of a way to get people to engage with comment, which is what Kim McGair did.

Since I have blocked her and her comments, I’m going a paraphrase. She basically said that if I ever actually went downtown, rather than staying in the safety of my home in the suburbs, I would see that things have significantly improved in downtown, but it simply wasn’t “my shtick.” Taking the bait, I asked her if she could tell me specifically how she thought downtown has improved (I was actually interested in her perspective, as Kim likes to say “I’ve worked in downtown for 26 years.” Congratulations, Kim. That’s truly impressive!). McGair said that there were fewer tents, but any other further explanation of her feelings on her opinion “would take too long to explain on X.” Now, this is truly a ridiculous claim, because Kim spent the better part of the next hour insulting me in any possible way she could.

I retorted that while I agree with her that there are fewer tents in downtown, there were several rather concerning aspects currently occurring there, including: 1) a new open air drug market around 13^th and SW Yamhill which had effectively shut down the largest clinic in downtown (Portland Clinic), 2) Portland’s downtown real estate had recently been devalued by nearly 60%, 3) the foot traffic in downtown is still below over 20% lower than 2019 numbers (not exactly the best year for downtown), and how there is still considerable political action that has turned violent and intimidating.

At this point, McGair went into the classic sea-lioning phase of her on-line assault that all trolls use. She said that unless I could provide the receipts for these claims, that I was lying (see the receipts in links above). Then, she informed me that I was a coward, that PDX Real is “a fraud that she will expose,” and that my life is obviously pathetic and miserable. Then, hilariously, McGair offered to “take me to lunch” so then afterwards we could “trade pictures of downtown” to see who was right, because, of course, I lived out in the suburbs, and I was too afraid to actually venture into downtown. Frankly, it is the utmost in narcissism that she expected for me to take a lion’s share of one of my busy days in order to have lunch with someone who is going to undoubtedly insult me the entire time. And of course, if I don’t succumb to this ridiculous demand, it would indeed prove all of what she was saying. At this point, all I’m hearing is Ennio Morricone’s The Good, The Bad, and The Ugly theme, the guitar and trumpet motifs rising as the penultimate Mexican standoff occurs between myself, Kim, and the City of Portland.

Of course, Angela and I don’t live in the suburbs. We live in Mt. Tabor. We have both lived in Portland for over 30 years. We have both previously lived in downtown or NW Portland, independently, for years. Out of curiosity, I looked up and found McGair’s address. Her house in the east side of Laurelhurst is a nine-minute drive from mine. I even tried to appeal to humor: I made jokes about attorneys and asked her how she could really see downtown from the 16^th floor of her office with its private parking. This only served to enrage McGair even further, because, in reality, her law firm (Farleigh Wada Witt) is only on the 6^th floor, but of course, still has private parking.

Now, I go downtown and NW Portland at least once per week for business purposes, sometimes more than that, so I regularly view the surroundings. I agree with McGair - downtown has gotten better, but the city has improved the core mostly by pushing the homeless into the Lower Eastside or further northwest of downtown. Also, my last Substack article was about how the city has removed 30k to 50k tents in the last year alone, so I agree with the claim that there are fewer tents in downtown. Is Portland better than it was in ’22 or ’23? Probably. Is it on its way to making a comeback? I have serious doubts.

The final bizarre twist in the McGair saga is that her law firm actually represents us. One of the attorneys at Farleigh Wada and Witt (I won’t mention his name. He’s a good guy, a good attorney, and would probably even consider him a friend) has worked on several different occasions for our businesses. The contract that we still use for our clients was drafted by this attorney. We still get emails and Christmas cards from McGair’s law firm. I even informed her of this a couple of years ago when she was harassing us back then, and she simply didn’t care.

I know many attorneys. Some are friends of mine. When I talk to them about this treatment McGair has shown, they are aghast. Attorneys are generally very careful individuals who are quite concerned about their professionalism they project in every aspect of their lives. It’s difficult to believe that one, especially with McGair’s experience, would want to be engaged in such online shenanigans (except for the leftist weirdo attorneys, of course).

I would gladly compare PDX Real’s efforts to change the city for the better against anyone in this city, especially someone like McGair. For example, before PDX Real began covering Multnomah County, the city’s residents were only too happy to blame the mayor for all of the city’s issues, even on things that were completely out of its sphere. The most obvious example is public health. It was the county that was responsible for boofing kits and needle exchanges. It was the county which was responsible for recovery beds and shelters. It was the county’s responsibility for keeping people arrested for a crime in jail rather than releasing them immediately back on the streets. Before we started covering the county, no one showed up to the county council meetings. Deborah Kafoury, the former county council chair had absolute carte blanche over county policy decisions with little to no pushback from the community, and she used this to her full advantage. PDX Real changed that. We covered the county extensively. We heavily promoted both Sharon Meieran for county chair and Julia Brim-Edwards for her district.

We covered and broke multiple important stories. We informed people about potentially harmful policies in the city, county, and state governments. We encouraged and trained people on how to show up at city and county council meetings and give testimony. We did heavy investigation into individuals running for office and senate and house bills which we reported to our followers, allowing them to make informed decisions. We interviewed people from every walk of life. We did homeless outreach on multiple occasions. We took journalists from around the country and around the world on tours of Portland. We helped multiple people on the streets, getting them ID’s, employment, and even housing. We placed homeless individuals into permanent housing, and even housed one young man who had been on the streets in our own home for four months. We organized multiple town halls that were attended by hundreds of people, including one featuring then mayor Ted Wheeler.

And through this all, we have endured a great deal. We’ve endured ridicule, threats, and harassment of every kind, as well as the near break up of our family. Have we made mistakes along the way? Yes, of course. Are we perfect people? Not at all. Have we put our heart and soul into helping this city and state, all the while enduring financial hardship for our commitment to this cause? Without a doubt.

According to Kim McGair, this makes us “frauds” and “cowards.” I’m sure she has her supporters in this perspective, and that is acceptable to me. We knew we were taking a risk and that we would need to have an iron constitution to weather whatever would come. As one wise person said, “heavy is the head that wears the crown.” As another said, “it’s none of your business what others think of you.”

On another topic and onto another one of Portland’s notorious loose cannons is the subject of Angelita Morillo. For years, PDX Real has regularly been publicly attacked by Morillo, undoubtedly because we were largely responsible for her former boss, JoAnn Hardesty, losing to Rene Gonzalez in their highly contentious 2022 city council election. Since that time, former staffers Matt McNally and Morillo have made wild claims about PDX Real, and especially, about Angela herself. While Morillo was a staffer for Hardesty, and then afterwards, she posted multiple mean girl TikToks about Angela, claiming all sorts of things, including Angela being a white supremacist, a racist, and an overall meanie.

Back in January, a mere few weeks after Morillo took her spot on Portland City Council, PDX Real figured out that the new councilors’ office numbers and emails were no longer listed on the city’s website. As far as we could tell, this was the first time elected officials in Portland, or the entire state of Oregon, didn’t have their information posted on-line. Coupled with the fact that during the council’s honeymoon love-fest phase, every council member seemingly regurgitated the claim many times over that this new council was going to be especially transparent and accessible. This seemed to indicate the opposite, so we did an investigation into what was going on and reported it to our followers.

We immediately contacted the mayor’s office and posted on our Instagram and X accounts about this lack of accessibility and asked our followers to contact the city to complain if they were so inclined, which I can only assume scores of people did.

Although Morillo was not singled out for this complaint, she posted on her official social media that what we reported was “misinformation” and went on to explain there was an online form to fill out to contact electeds – meaning, concerns couldn’t go directly to an individual representative in the city district.

Soon after this, Morillo went on her personal TikTok page and posted something far more personal and slanderous, claiming that the original complaint came from “a woman who spends all of her time hanging out with Proud Boys and harassing women of color who run for office.” She also claimed that anyone who had a problem with the policy were just engaged in hatred and not “actual people.” One has to wonder who “actual people” are to Morillo. To Morillo, it seems to be only the people who agree with her radical political views. Our substack on what happened is here.

First, Angela and I obviously don’t hang around with Proud Boys. I think we have met one or two previously, but we have also met many, many more anarchists and communists in this town, as well as others from every possible political affiliation or group. Secondly, reporting on individuals who’s ideas we believe are bad for this city and providing our personal feelings about such people is hardly harassment. Can we be harsh? Yep. Does it matter what color or race they are? Nope. I mean, Angela herself is multi-racial. Angela was formerly on the NAYA board during the time that it was building its family center.

On the same night of the slanderous Morillo video, Angela went to a District 3 community meeting in which Morillo was in attendance. At this meeting, Angela asked the District 3 councilors about this lack of accessibility as well as asking Morillo directly whether she thought it was appropriate to slander her constituents in the way she had. Of course, she never answered Angela’s questions, and rather than dealing with the question in a transparent manner, it was shut down by moderators. It was at this time when we first became aware of Morillo’s right-hand-man, Andre Miller. In the video of the event, Miller can be seen motioning to the moderator to interrupt Angela’s question in order to shut down her comment. I think it was less than a month later that Miller caused controversy at a city council meeting when he attempted to intimidate two older women at the meeting. He actually mean-mugged them when they attempted to give their testimony, and then later had a confrontation with the women out in the hall. Miller told the women that he “only wore this suit for show, and I’m not the one.” Meaning, don’t mess with me or bad things are going to happen.

Miller is also a former Hardesty staffer and a self-identified activist. As a matter of fact, Miller was downtown in the middle of the worst of the George Floyd riots in Portland. He was injured by a police projectile during these riots and did what all anarchists and cop-haters do: he successfully sued the Portland Police Bureau. Here’s a picture of his boo-boo. I think I might have hurt myself worse when I bumped my head into the hatchback of my car last year.

Interestingly enough: the commissioners now have their office emails available to the public.

All of this comes down to one thing: PDX Real is tired of trying to save a city that is obviously unsaveable. In 2022, we believed we were making considerable headway with the election of Rene Gonzalez and Julia Brim-Edwards, and then in 2024, with the victory of Nathan Vasquez over Mike Schmidt. That has all changed. The new city council now is one half either full socialist or socialist adjacent. Many of them are vehemently anti-cop and anti-business. We have also elected a very weak mayor in Keith Wilson, who refuses to give any kind of pushback, and actually sent out this email to his constituents today:

We are facing a significant budgeting crisis, while three months in, the city councilors are still flailing away attempting to figure out what their jobs are. While the city is in crisis, nothing is getting done, except talk about building Pruitt-Igor-style “socialized housing” projects and refugee housing. There are maybe five individuals (Dan Ryan, Loretta Smith, Eric Zimmerman, Olivia Clark, and Elana Pirtle-Guiney) on the council who have the intelligence, experience, and demeanor to run the city. The rest are a pathetic joke that is being played out on the innocent residents of the city - the one’s who pay taxes, anyway.

Honestly, I have to congratulate them. These people went out to take over our city with ranked choice voting and a new government, and they’ve been largely successful. If anything, they are relentless in their pursuit to “re-imagine Portland,” which of course is just woke-speak for turning it into a socialist and unlivable Hell hole. The true tragedy of this scenario is I still love this city. I love taking my dogs to the park. I love many of the people. I love my little neighborhood and its world-class eats and bars (especially thanks to our friends at Tinker Tavern, Arbor Hall, Redwood, and the Observatory). I love the Oregon outdoors! Shit, I even love the weather a little, especially when the sun comes out.

But Portland is a bad copy of a copy of a copy of its former self. The color and the light of it is gone. Obviously, I travel a lot. Every time it is time to return to Portland, it becomes more difficult to return home.

At this point, there is no point in engaging the way that we have. We aren’t going to kill ourselves to save this city, because, as I said earlier, it is beyond saving. Richard Cheverton has seen it all before in multiple cities, Detroit being the most obvious example. He knows all the signs and all the stories, and Richard can see the writing on Portland’s graffiti-stained walls, and I can as well. The lunatics are always going to at the gates in this city. You can feel it in its dark, black, little pee-sized heart. I think a part of me used to be drawn to that, but no longer. And others, such as Bojack himself, recently said that he was done, saying much as what I have here: “As the 2024 elections showed quite clearly, the voters here simply will not give common sense a chance.”

I will still write, and occasionally post. I enjoy writing. It’s true catharsis and makes me happy while things fall apart. “The center cannot hold,” as W.B. Yeats once wisely said. And the rough beast is coming, slouching towards Portland to be born. It is inevitable as the rain. Also, Richard and I have started filming a podcast, called “Bourbon and Bullshit” where we drink good bourbon and talk shit about Portland, because that is all there really is left to do. And eventually, we will be gone, to one of those other cities I mentioned above that don’t abuse their residents in the way that only Portland uniquely can.

One thing that I’ve learned in being in smaller countries that sort of “get it” is that although they argue and even fight, Hungarians are Hungarians, Czechs are Czechs, Croats are Croats. They fight for each other. If people in this country can’t even manage not to shred their supposed allies to pieces, what chance do we have to make it work for those who oppose us. Americans aren’t Americans any longer. I don’t know, maybe they are in North Carolina. At least there and other places, we won’t be taxed into oblivion.

By the way, Kim McGair. I don’t choose to go downtown because I’m afraid. I don’t choose to go downtown because it fucking sucks. Except when the Cherry Blossoms are in bloom. That’s pronounced “bloom,” not “blum.”