In recent decades, no major American city can match the sharp ups and downs of Portland, Oregon. From a poor but pretty backwater burg of white gearheads and provincials in the 1980s, Portland underwent an exceedingly unlikely – and quite radical – transformation to become one of the country’s most distinctive and culturally vibrant urban renaissance stories in the 2000s (the New York Times memorably declared Portland “cool and refreshingly unneurotic” in 2007).
But then, in the 2010s, the self-described “weird” and fun city, experiencing a rapid influx of young and educated newcomers drawn by post-Portlandia “where young people go to retire” hype, experienced what writer and journalist (and former Portland resident) Nancy Rommelmann has dubbed “Portlandization.” As the decade wore on, she wrote, Portland became increasingly enamored with ostentatious displays of performative virtue signaling and the militant policing of increasingly narrow and rigid progressive orthodoxies. Then that all exploded into the seemingly endless – and endlessly destructive – protests that roiled the city in 2020, which combined with a failed experiment in the decriminalization of hard drugs to bring the city to its knees, and from which Portland still has yet to fully recover.
So we asked Nancy Rommelmann, who has written extensively about Portland’s travails for Reason and Tablet and on her Make More Pie Substack page (she also co-hosts the popular Smoke ‘Em if You Got ‘Em podcast), to join us on BCB to unpack what went so wrong with Portland’s fairy tale rise and why, and where the city stands today (Rommelmann left Portland in 2019 but visits frequently and continues to write about the city).
In our conversation, we trace Portland’s evolution first into a creative, affordable, rising city and then into a symbol of blue-city political and governance struggles. We discuss Portland’s food and cultural boom in the 2000s, the growth of ideological conflict and “outrage culture,” debates around #MeToo and due process, the 2020 protests and attendant unrest, the impact of Oregon’s drug decriminalization experiment, and broader tensions within progressive urban politics.
While Nancy is largely critical of Portland’s recent trajectory, she also acknowledges the legitimate social grievances that have animated the city, and she sharply critiques right-wing and Trump administration efforts to distort and politically capitalize on Portland’s much more benign recent ICE protests, and she ends our conversation with cautious hope that Portland will fully recover.
“I get accused of being like a real naysayer about Portland, and I do have bad things to say about Portland, but I do wish good things for the city, because it's a beautiful city,” Nancy tells us. “The food is can be great, you can grow anything, and why would I not want it to fly again?”
Our editor is Quinn Waller.
OUTSIDE SOURCES:
Nancy Rommelmann, "Portlandization: It Can Happen to a Place Near You," Tablet Magazine, July 11, 2019.
Nancy Rommelmann, "The Dream of the '90s Died in Portland," Reason, March 22, 2021.
Nancy Rommelmann, "Drugs 1 - Oregon 0," Make More Pie, Feb. 29. 2024.
Nancy Rommelmann, "Trump's Troops Return to a City That Moved On: Dispatch from Portland," Reason, Oct. 6. 2025.
Please send your feedback, guest and show ideas to bluecitypodcast@gmail.com
[00:00:10] Hello and welcome to the latest edition of Blue City Blues, a podcast featuring smart guests talking about the problems facing blue cities and how to fix them. I'm David Hyde with Sandeep Kaushik and Sandeep listeners to this podcast will know that we were classmates at Reed College in Portland, Oregon back in the 1980s.
[00:00:29] And I'm wondering if you remember this Gus Van Zandt movie, Drugstore Cowboy, starring Matt Dillon about this band of kind of unruly junkies who are robbing drugstores. It's set in like the early 1970s, super dark subject, also super funny, never put a hat on a bed. And at the time, like, I love this movie. I felt like it was Portland's answer to Repo Man, super gritty.
[00:00:54] I'm just going to point out to you, Sandeep, that we were sort of romanticizing that era in our recent episode with John Roderick that's up now. Yeah, well, I mean, we're romanticizing our youth, David. And frankly, like, I think we kind of thought back then in the 1980s in Portland that we were living in a Gus Van Zandt movie and maybe in some ways we were, right?
[00:01:17] I mean, my memories of sort of Portland cool in that era was, you know, bowling a 3 a.m. frame at Grand Central Bowl or getting a shoeshine and a drink at Kelly's Olympian or, you know, kind of drunken 2.30, you know, breakfast at the hot cake house or, you know, I mean, standing or standing on a street in Old Town, right?
[00:01:40] Outside of Satyricon, the old punk rock club, eating a souvlaki at like one in the morning with all the horrors and the junkies, right? And, you know, that was Portland back then. It really was. Yeah. And today we're actually talking about Portland with Nancy Rommelman, author and reporter for publications, including The Wall Street Journal, The New York Times, Reason, The Atlantic.
[00:02:03] She hosts the podcast Smoke Em If You Got Em, which is a great podcast title and writes the substack Make More Pie, which focuses on politics and culture. Nancy Rommelman, thanks so much for joining us. Thanks for having me. I love to talk about Portland. What about Drugstore Cowboy? Also, you include a Drugstore Cowboy reference in your substack piece. I'm going to quote here. You're talking about drug decriminalization and that whole problem for Oregon.
[00:02:29] But when I moved to Portland in 2004, the junkies in downtown's Pearl District romanticized in Gus Van Zandt's 1989 Drugstore Cowboy had been replaced by farm-to-table restaurants and a flagship REI store. It sounds like you're not romanticizing that earlier, Portland. You kind of like this new Portland that you moved to in 2004. Well, let's back up. So my husband who was born, my former husband who was born in 1867, grew up in Portland.
[00:02:59] We were living in Los Angeles and he said to me, we were looking to buy a house, trying to buy a house in LA in 2003 was ridiculous. And he'd been going up to Portland because his grandmother was on the way out. He said, Nancy, it's not the horrible, depressing city it was when I grew up there in the 70s and 80s. Let's go look. And, you know, it was May. So it's Planet of the Plants. His mother's gotten us all the propaganda stuff, the opera, the schnitz, the farmer's market.
[00:03:26] And I mean, it was nice. It definitely was nice. It wasn't like I was looking for bourgeois. Definitely not. But it was not Drugstore Cowboy, which, come on, it's Matt Dillon. Yeah, Kelly Lynch. But, you know, Kelly Lynch, all we needed to do, though, guys, was wait till Measure 110 passed and then we could get some more of that junky stuff going. But I'm sure we'll get there.
[00:03:55] Yeah, no, and just, I mean, people who listen to this podcast know this, but I discovered heroin in Portland in the 80s and it derailed my life for the better part of a decade. So, I mean, I have a romanticism about the Portland of that era, but I also have no illusions about, like, you know, how gritty the city was and, you know, the dangers that were sort of built into that era of the city.
[00:04:23] And, you know, it definitely, yeah, it definitely took me off track for a while. But, Nancy, let's, you were mentioning you moved to Portland in 2004 and it's a cool city then. You're digging, living there, right? Like, what, explain the vibe and what it was about the city that appealed to you at the time. Well, it appealed to me because my husband wanted to move up there. We were able to afford a house.
[00:04:51] My daughter started high school. She went to Grand High School when we got there. She started ninth grade. It was new. I'd been in L.A. for 18 years. I'm a New York City girl. The issue for me with Portland, I found it small. I remember saying to my husband, New York, L.A., Portland, what's the next stop? Anchorage. But I also found it, you know, people were very nice. The prices were really good. Like, you could go out and get a really nice steak dinner for like 40 bucks. I was like, this is nice.
[00:05:21] And it was a new field. I liked it. It felt provincial. At that time, you really didn't have the sort of loud, angry, progressive element at all yet. I mean, Reed, of course, you're going to get some of that where you guys went. But it was still kind of an interesting mix or maybe a balanced mix of older Portland, the kind of, you know, fences make good neighbors people and the outdoorsy contingent.
[00:05:50] And then people that were coming in from all over the world, which I loved, really building the restaurant scene, which I had written about food in addition to the other stuff I write. I found that really interesting and fun. I mean, it was getting to be almost a cosmopolitan city. And as a New York City girl, I dug that. And we were definitely there for the rise, for sure. Probably started a few years before we got there.
[00:06:17] But, you know, Portland from, I guess, around 2002 to maybe 2012, you know, not counting the crash in 2008, really was on the up. It was a city on the up. And then it decided to shoot itself in the foot. And, you know, it's still limping to this day, for sure. Before we get there, I wanted to take one other small detour just very briefly. You mentioned restaurants.
[00:06:46] And I was just thinking about you coming from Los Angeles and encountering a fast food place that might have still been there when you moved there that was popular at the time when Sandy and I were there called Machismo Mouse, which was this kind of antiseptic, supposedly, like, healthy, but really kind of not very good version of a Mexican restaurant.
[00:07:10] And, I mean, it kind of captures the sort of provincial progressivism of Portland, at least in the 1980s, in some ways to me, in terms of the type of restaurant that it was and the type of folks that it appealed to. I mean, honestly, I went there all the time, so I'm not self-judging. But I don't know if you or Sandeep remember that place. I think it was gone by the time I got there. But I also think that something tragic happened with that, like some guys that owned and dined in a plane crash or something.
[00:07:37] I remember hearing about Machismo Mouse and hearing some, and I'm sorry, I don't remember, and I hope I'm not getting this wrong, but there was some tragedy associated with it. We'll have to look that up. Yeah, it was like Mexican. I do remember it. It was Mexican. They put, like, orange juice concentrate in their, like, burrito sauce, I think, was their say. And it actually was. Anyway, let's not get off on a Machismo Mouse sort of sidetrack.
[00:08:02] But just coming back to it, I mean, so Nancy, you wrote a piece in Tablet back in 2019 warning about what you called Portlandization, right? And that it could happen to a city like yours. And in that piece, you recount kind of your trajectory coming to Portland. And you say in that this earlier period in the aughts, like, you say Portland is authentically interesting, right? Yes, provincial a little bit.
[00:08:31] Yes, these people are a little offbeat. Yes, we're kind of off on the edge of the known universe. But it's kind of welcoming and, you know, easy place to live. And there's sort of kids doing cool stuff, you know? It was the last sort of affordable West Coast city. So for people that maybe couldn't open a restaurant in San Francisco, they could come to Portland and do it.
[00:08:57] So you had a lot of young, very industrious people in this incredible breadbasket up there. You know, as I've said before, you know, you spit out a watermelon seed in the fall and in the spring or the summer. You've got a whole garden of watermelons. There's just food everywhere. You can make whatever you want. I used to joke if they could make their own water, they could. They would. It was very, very hands on. I'm sure there was a lot of failure, but there was a lot of interesting success.
[00:09:25] And a lot of it was affordable things you could interface with. Cocktails, ice cream, you know, bee balm, booze. I mean, we had so many friends that were making things. You know, the aviation vodka guys and my friend Troy McLarty was at Lovely Houlihan's. And now he's got like just interesting people making delicious things. I mean, there's not you got to eat every day. Right. So that was really fun. But then it started to change.
[00:09:55] And we can use, again, food as one of the instances. The girls that came back, they had been like these young 20-somethings. They went to Mexico. They watched how these women made homemade tortillas. So they opened up like a little burrito, a food truck. And they were destroyed for not being Mexican and went out of business within a week. They got death threats. It's somebody started running with this because you know what happens. Like, oh, that's a hot editorial story. Let's do it again.
[00:10:24] Somebody created a list of one of these, you know, sort of like a shitty media men list. You could just like put names on there anonymously for like name all the restaurateurs who make a food of their, not of their ethnicity, including Andy Ricker of Pok Pok, who had literally been one of the biggest people to put Portland on the map with his food. The late Jonathan Gold of the LA Weekly, who was a friend I wrote for the LA Weekly for 20 years. When he came to Portland to visit, he wanted to go to one restaurant and that was Pok Pok. And I took him to Pok Pok.
[00:10:54] I think we met Andy Ricker when we were there. Andy got called out. And you know what he said? Okay, fuck you. He left. Got rid of all the shops. He lives in Thailand. And it's like, it was so delicious to people. Sorry, not trying to make a pun to bring down the people that they had lifted up. And I think part of the reason for this, and I could be wrong. It could just be what was in the water and the arc of the culture.
[00:11:21] But I did a piece in the Oregonian in 2010, a long opinion piece called Is Portland the New Neverland? So let's say you are in college on the East Coast and you hear about this incredible place, Portland. You can live your dream, right? And then you get there in 2010 and rent isn't $85 anymore. And like, it's even hard to get a barista job. And really what you want to do is raise a chicken and smoke pot and be able to be part of this community. But that's not working anymore.
[00:11:50] But why is it working for those guys? And then you start to get a little disillusioned. And then maybe you turn that disillusionment, you turn it around and you start aiming it at the people that are successful. And that's what they did in Portland. They started to, just like in the rest of the country, they started to take people down and then got addicted to the taste of other people's blood. And it was an ugly time. It's had some really bad, I think, downstream effects that we can talk about.
[00:12:21] And I don't think Portland is out of the woods yet, though. Though, we'll see. We've got an interesting election coming up. So I'm sure we'll get there. Yeah, interesting. Like, again, like one of these academic concepts that has some usefulness sort of within the halls of the academy, but then you take it out into the world, an idea like cultural appropriation and people just start abusing and misusing it as a persecution tool.
[00:12:47] And you also write about the Me Too movement. And this led to some problems for you as a Portlander in like 2019. 2019. So there's a gal named Leah McSweeney. She actually went on to be a real housewife of New York. She was writing for Tablet at the time. And I was writing for a reason. We both had written an article about, it's a little bit of a long backstory here, but about this actress named Aja Argento.
[00:13:15] So she got accused of sleeping with an underage boy. Her boyfriend at the time, Anthony Bourdain, was paying off the boy who was now a young man. He committed suicide. She played the victim. And she was also one of the faces of Me Too. She was one of the main sort of Harvey Weinstein accusers, though she had, after she said he sexually assaulted her, she had, I think, a 10-year consensual sexual relationship with him. So I thought this was sort of a nuanced thing.
[00:13:43] We were looking, it was 2018, we were being asked to wholesale support Me Too. And, you know, I was like, well, good idea, but what about this? Do we want this person to be the face of Me Too when she's got a lot of issues here, man? So Leah was writing about this. I was writing about it. We decided to do a little podcast that a friend of mine, my boyfriend actually titled Hashtag
[00:14:08] Me Neither, which was a bit incendiary at the time, didn't really realize it. But what we talked about, it was a video podcast. We only did five episodes. We basically talked about due process. We talked about, you know, the Kavanaugh hearings. And we talked about people like Aja Argento being a hero of Me Too. And we talked about, do we really want, you know, an Aziz Ansari to be treated the same way as an R. Kelly? I thought it was, it's very practical stuff that you can talk about now, but you could
[00:14:37] not talk about it then. We were a little ahead of the curve. And as it turned out, a former employee of my former husband's business, he had a really successful string of coffee roasting and cafes in Portland called Ristretto Roasters. She saw this. She got mad. And she got some employees to sign a letter saying that my podcast was vile and dangerous and put the employees in danger. And by extension, the people of Portland. And it was the era.
[00:15:07] It was January 2019. And the press just ate it up. I will add that I just had a big book come out six months ago. I don't know if you remember that case where a woman threw her two kids off the bridge in Portland, Oregon in 2009. I wrote a book called To the Bridge. And I was kind of like successful at the moment. So I was an easy target. Unfortunately, very, very, very unfortunately, the people that bore the brunt of it was my husband and his business. They couldn't really do that much to me. I wrote nationally. I had a book out.
[00:15:36] Like, what are they going to do? But they could boycott my husband's business and they could really get some traction there. And the business did go out of business. So that was not great. And then we wound up just pulling up roots. You know, we actually, I don't know if I've said this on the air before. The day before this happened, we'd actually gone to a business broker because he wanted to sell the business. He'd had it for a number of years, 10 years. He was ready to kind of move on. I was spending half my time in New York.
[00:16:05] So we're in a life transition. And then it just transitioned very quickly without our help. So, yeah, that was that story. But yeah, it's stuff we talk about now very calmly. But it was very hard to have certain conversations in 2019 and certainly 2020 when, you know, everything, the temperature just ramped up so much because of the pandemic.
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[00:17:33] Sandeep and I would really appreciate that as well. Okay, back to the show. Yeah, I wonder if you could just say a little bit more because I think it's hard for us to remember this stuff. And a lot of people, I think, kind of want to forget the origins of what you're calling outrage culture in this piece in the Los Angeles Times. So I wonder if you could just say a little bit more about what was kind of percolating in the
[00:18:02] water in blue cities like Portland at that time that led to that sense of outrage. Look, it has been the case historically that, you know, women were not believed when they had accusations of sexual assault or rape. There's probably tens of thousands of rape kits in this country that are just sitting. And when the opportunity came, when, you know, Weinstein just exploded like a bomb, people were like, I have a story too.
[00:18:30] I remember when, you know, the first hands went up on Twitter, you know, raise your hand if you've been sexually assaulted. Of course, I raised my hand. Every, almost every woman has had someone do something to her that she didn't like. Right. And all of a sudden it was like, wow, there's solidarity here. There's recognition here. Maybe we're going to create some change that I think that was happening anyway. But this sort of, you know, turbocharged it.
[00:18:57] But it also became a vehicle to get personal attention. And it was like, I'm a hero. I'm, I'm, I'm a victim. I'm a hero. I want love. I didn't feel loved. It became a slippery slope. You know, there were my friend, Barry Weiss. I remember she was at the New York Times at the time. And she wrote a piece where, you know, it's like, do women lie? Of course they lie. Everybody lies. Children lie. Women lie.
[00:19:26] And there were false accusations for a sense of maybe self aggrandizement. But you were never allowed ever at that time to bring anything like that up to say that Aja Argento wasn't a hero full stop because then you were against women. It's like, no, man, that's not the case. I'm for due process. I'm for due process for anything. If I walk into a store and I walk out and I paid for my pack of gum and you run out and
[00:19:54] tell me I didn't pay my pack of gum for my pack of gum, I want due process. If you tell someone that they have sexually assaulted you, I mean, we have the shitty media men list that came out. All of these people that were making the accusations were allowed to be anonymous. We had Title IX where accusers were allowed to be anonymous, where people were not allowed to defend themselves. This is not America. This is not the justice system. I want women to have justice if they have been sexually assaulted or men in some cases.
[00:20:24] And I want the people that have been falsely accused. I want everybody to have their day in court. And that was not what you were allowed to do in 2019 and 2020. You had to just stand in line and say, we know where we are because we're the good people. And I just thought that that just can never be so. You've got to look at every case individually. And that was not a popular opinion at that point. Yeah.
[00:20:51] And that seemed to me like this unwillingness at that point to accept any kind of nuance or complexity around what is even an important issue like the lack of recognition of sexual assault in our society. Right. It's kind of emblematic, right, of the larger trend in the larger cultural trend in blue cities like Portland, like Seattle, like really across the country, cosmopolitan culture more generally.
[00:21:19] And that story right now we're in the kind of late 2010s. Right. That story between from when you get to Portland in the middle of the aughts to the middle of the middle to late 2010s is a story of one, it's sort of bougiefication. Right. It's all of these young, educated kids looking for a new life, moving to cities like Portland and the city upscaling, prices going up, all sorts of stuff happens.
[00:21:49] But it's also this cultural shift within progressivism itself. And so Nancy kind of kind of, yeah, speak to that. Right. We see a real change away from the ideals, which are supposed to be about tolerance and acceptance and stuff, into something much more authoritarian. I can tell you, you know, when it was like 27, I mean, the election of Trump did a lot of this. People just lost it.
[00:22:16] Everybody, you know, on both sides, whether you went super MAGA or when you went super deranged syndrome. But there was a sign in Portland, you probably remember, it was probably in other blue cities too, saying you are welcome here. You are safe. Everybody is welcome. Well, that was actually not the case. I have a friend who had a cafe in North Portland and she got a call from her barista saying, do I have to serve this guy? And she's like, what guy? She wasn't even there. She's like, what guy? He's like, well, he's got on a MAGA cap.
[00:22:45] And she's like, is his money green? Yeah. Yeah. You got to serve the guy. You know, a lot of the people that came, obviously, I was one of them, were not Oregonians. They didn't grow up there. And, you know, they came and I think they thought, well, now we're going to make the city in this idealized progressive image.
[00:23:09] But if I think if the city had stayed like mostly locals, like my former mother-in-law or my neighbors, some of my neighbors, I lived in Northeast Portland right off of Williams. I don't think we would have seen this. People like kind of like want to go about their business. They want to go kayaking on the weekends. You know, they're not, they're not about going downtown and setting the courthouse on fire. But the new peeps, they were like, wait a minute. We have an opportunity here.
[00:23:36] We have an opportunity to make this the ideal liberal city. And if we have to burn it down, okay. But the problems that I saw with a lot of this, because as you guys probably know, I covered the riots and the protests very intensely. I was on the ground for months. They had this idea they wanted to remake the city. And step one was to burn it down and to get rid of everybody that was in power. But they didn't really have a step two.
[00:24:05] And that's why I say that Portland shot itself in the foot. And we're seeing the mad downstream effects from that. I'm quoting you here, Nancy, taking to task, Blue City, Portland, Blue City, public officials and citizens really for the atmosphere around the protests that happened in 2020. Talking about, in fact, the real sense that Portland had some serious issues and some things to answer
[00:24:35] for in terms of oppressing its black citizenry. In 1844, the provisional government of Oregon had voted to exclude black settlers from its borders. Redlining continued through the 1970s. The city has seen its share of horrifically racially motivated killings. So you're on board with the idea that there have been some problems that need to change, clearly. And yet what you saw and what you were reporting on happening in 2020 didn't seem like the right
[00:25:05] form of protest. I mean, what was your critique of the of what ended up happening in Portland? So it was, you know, it started in May right after George Floyd was killed. A couple of days later, you know, they 10,000 people marched over the Burnside Bridge. That's a lot of people. And who was leading them? Damian Lillard of the of the Trailblazers. It was a big moment. And it was a it was a cool moment. I wasn't there for that. But what happened right on the heels of that walk over the Burnside Bridge, they go over to
[00:25:33] the, you know, the the cop shop over there, the police station, they protest. And most of them go home. Oh, but we 100 or so they break into the police station. They start burning it down. They throw desks around. They break the furniture. Meanwhile, in the basement, there is a woman who works for the police checking some in prisoners. Prisoners can't get out. There's a fire. She's getting a phone call from her family members going, your building is on fire and you need to get out. And they're trying to the protesters are trying to bar the doors.
[00:25:59] OK, this is not this is not working for for peace in the wake of George Floyd's killing. Yeah, I mean, Portland was very, very white. Most of the protesters were white. I've told a story. I've written about it several times. I'm in the street one day because I was in front of the courthouse and the police station for many, many nights. And there's a young blonde girl and she runs up to me and she screams, the police are killing the street. And she runs away.
[00:26:28] And I'm like, I know as a journalist that to date, there had been two people killed by police in Portland and they were both white. But don't confuse me with the facts, as my late father used to say. They needed to believe that they were being besieged. One of the reasons for this is because, hi, we were in a pandemic. Portland is a young city. People were at home. They couldn't go out. They couldn't go to shows. They couldn't go to bars. They couldn't go out and fuck. They couldn't do anything. They were home.
[00:26:57] Oh, wait a second. I can get out into the streets with my friends and save the world. And I'm going to do it every single night. And it was orgasmic. It was a way to feel something when we were really, I mean, the pandemic was really, really hard on a lot of people being sequestered as we were. And so in order to justify that every single night and the violence that was going on, you have to say, we are besieged.
[00:27:26] We are being killed in the streets. There was one murder in the streets in Portland during the protests in 2020. And it was of a Trump supporter by a so-called, you know, big BLM supporter. He was not. He was a very, he'd had his black power fist tattooed on his neck a few months before. But there had to be that amount of danger in order to get the sort of, you know, gossip
[00:27:53] train going that justified the continued level of violence for 200 plus nights. And so, I mean, Seattle had it, you know, Seattle had a rough time in 2022. We famously had Chop Chas, the autonomous zone and, you know, all of that stuff. But Portland took the cake, right, in terms of a kind of protest culture that veers into
[00:28:18] something that maybe begins in a good place and in an authentic place, but veers into something very, very different. And as you say, fundamentally destructive and self-destructive. And look, I mean, Portland has long had a kind of organic protest culture, right? The first President Bush sort of famously dubbed Portland in the early 90s as Little Beirut because of the protests around the Gulf War that happened back then. I forgot that. Yeah, right? I mean, I remember that vividly at the time.
[00:28:47] I don't want to interrupt, but do you know the story about the Reed College protest when George, this is H.W. Bush came to town, Sandeep? No, no. I don't remember that. Where the students ingested red, white, and blue food coloring and then vomited up the American flag. I mean, it's kind of great. Pretty creative. It's kind of great. That's a great protest for them.
[00:29:13] Like, you know, shout out to our compatriots at Reed College for being creative and funny in that instance, right? I mean, between reenacting the crucifixion and vomiting up the flag like Reed College had its moments. But yeah, so there was this organic protest culture, but this thing was on a different, it was different, right? And to me, as I was watching it go down in Portland in 2020, it felt to me like I was
[00:29:39] watching a city full of kind of aimless, young, somewhat lost, mostly white kids craving authenticity of some kind, right? And Portland in that era now had become all about hipsterism and kind of second order, ironic detachment of kind of post-Portlandia world where authenticity itself was in short supply, right?
[00:30:02] I mean, there was a lot of diversion in the city, but not much vitality, right? I mean, how much meaning is there in the middle of a voodoo donut? You know, I mean, and so when those protests came along, it felt to me like they were offering something that seemed real and important to these kids, a mission, a struggle, a cause, something to latch on to.
[00:30:26] And, you know, smash a window, throw a rock, burn a mattress, tag the wall of the precinct house. It was like a blow against the simultaneously, oppressively twee and yet overly indulgent bourgeois overclass or something, or am I getting this wrong? I mean, what were they up to? I think that people do want to struggle. I think going back to what I was saying about like, where's my piece of pie?
[00:30:52] You know, I call my, my sub stack make more pie because it's not like there's one pie and we all get a smaller and smaller piece. You just make more pie. But at that point they were looking and saying, I didn't get mine. Now I'm stuck in the house. I don't really know what to do. And I believe with you, I agree with you, Sanjeev. They were, they were very immature. Now, you know, the Antifa kids will tell me, you know, no, we're, we're the ones that have the solutions here or actually they wouldn't tell me that they wouldn't, they would barely
[00:31:22] talk to me because they kind of couldn't. I've used this analogy a bunch of times that they kept their, their ideology in a soggy box. And you throw in like one actual question, like what's your goal here? And the whole bottom of the box blows out because they can't, they've got slogans, they've got energy, they're with their friends, but they don't have any solutions. And then probably you'll just also tell you solutions are for, you know, solutions are for squares or whatever. We're just here. We're here to make change.
[00:31:50] And they can do that by leveling a building, but they can't actually make change because they haven't, they haven't gone that far. And you will notice that when did they stop protesting? When did they stop protesting? I mean, I was told when I was, um, I was told like in, in May and June and July and August, oh, well, don't you think that if Biden wins, then they'll stop? I'm like, are you high?
[00:32:18] They don't, they just want to keep fucking shit up. Right. But they did go inside and stop protesting when it got cold out. No, I remember when Biden got elected, there was a big pro, right? I mean, and this is the thing, the protests kind of became an end in themselves. Right. And it wasn't clear what they were about anymore. I mean, it started out about police brutality, but then it was about Biden and or, or Trump or, yes, or capitalism or, you know, who knows what it was about, right?
[00:32:47] The biggest night, the biggest night of violence, um, was the day after, um, Biden was elected. I was in town. I marched with them, walked. I mean, it was huge, huge thousands and thousands of people marching from the park blocks down by, um, um, by like kind of where the Broadway bridge is all the way up going up Broadway, people screaming. Also people on their balconies going, will you please stop? They were so done with this.
[00:33:16] And then going down past the poor Apple store, which was raped so many times. This had this giant fence around it now. And we get down to the waterfront and there's like, like a lot of people and a lot of noise, but there's also a podium with local leaders, politicians, activists, kind of grownup people. They've got a band, they've got food and they're calling, they're calling to the little Antifa
[00:33:42] people in their, in black block going, come and join us. Be part of the solution. Absolutely not. That is not what they wanted. They marched back up and I watched them smash in the windows of all the stores along the way because they could. And because it felt good, they didn't want to give up that sense of actual physical relief. Uh, and again, they didn't, they didn't really stop doing it until they kind of ran out of
[00:34:11] steam in January and it got cold. And then they're, they really, I mean, you still have, you know, ice comes to town. I've been there covering that. They will protest, but nothing like what, nothing like what we saw in 2020. The thing is if property destruction actually worked to solve racism or reform the police or whatever, I mean, I could certainly make the case for it right here, right now. It just doesn't.
[00:34:35] And the problem isn't just the anarcho libertarian class of bougie, mostly white kids that are out there protesting and, and still have those views by the way in blue cities. It's the people that basically agree with us that that sort of activism, either it's wrong or it's counterproductive, like smashing up as you write about this, um, Palestinian owned
[00:35:00] business in Portland in 2020 isn't doing anything other than, um, destroying the lives of, uh, those business owners and their employees and making it harder for them to just make a living. And it's, it's just obviously the wrong target. It's so stupid, but it's the, it's the people that are like kind of unwilling to differentiate between these folks and peaceful protesters as you write, but also just people who again, agree with the three of us about this stuff, but weren't willing to say so aren't willing
[00:35:29] to say so don't want to make those distinctions for fear of being called out. That really was the, was the mood back then, right? Just that sort of, you know, neo-totalitarian mental space that was so oppressive. I'm writing right now about those, those trenches that people started madly digging so they could hide in them. So they didn't have to like walk the figure of sniper alley and get shot in the head.
[00:35:56] If they decided to say something that sounded, wasn't exactly what everybody else was saying. Well, you know what? I'm sorry. I'm cursing on your show. Fuck that. Like just, you gotta, you gotta have some courage. I get it. I get it. I get why people don't stand up for their friends. I get there's, you know, they've got jobs, they've got kids. They're afraid, but you gotta, you gotta speak. Even if you're wrong, like if you're like, I don't know, man, seems to me like maybe it's not a great idea to smash in this guy's window.
[00:36:25] You have to say that. And if you don't, well, you're giving more power to the people that are just going to shout you down and tell you you're the bad people. Well, no, I'm not. I'm going to stand here and tell you it is not okay to destroy people's businesses. And you know, people that are doing that, I remember when the whole terrible thing happened with my husband's businesses and so many of the baristas, many of whom were kind of
[00:36:52] like rich kids who'd gone to Smith or gone, whatever, they could quit their jobs because you know why they had a cushion. But I remember one young woman, I don't know her name because I wasn't really around very much. I've been on book tour. She couldn't quit because she needed the job and she needed the money. I wonder how many of the people that are doing this destruction, like if they owned a small
[00:37:18] business themselves or if their parents did, would they have been as like game to smash these things down and destroy someone else's livelihood? It's it's it's really decadent, actually. It decadent and it and it got really nihilistic, too. And, you know, as you say, it was like sort of the destruction became an end in itself. I remember when I think it might have been a Reed kid who did this, like smash the windows of the Oregon Historical Society. Right.
[00:37:46] And then kids ran in there and they spray painted it all. I can't remember what all they spray paint. But basically, they were they were very kind of explicitly attacking the idea of history itself as having any meaning. Right. Like they were they were basically saying, like, history is just a story. Everything in the past is just a story of racism and oppression or whatever they thought and therefore should be, you know, denounced. Right.
[00:38:11] Like they were kind of it was this incredible sort of free floating moment of I don't know what it was existential like, you know, hubris or something. Well, I mean, if there's no history, if you're the only people, then, you know, axiomatically, you look more important. I have a video. I didn't actually take it, but I've used it in a number of pieces that I've written. After that person was murdered, the Trump supporter was murdered.
[00:38:39] That night, there was a girl in black box standing with a megaphone with about 35 people around her. There's fires in the background. And she was they were applauding. They were applauding murder in the street. They thought it was good. They were stoked that this guy had been murdered in the street. And I said, that is a death cult. And if you think if that's what you want, welcome to it. You're going to build it.
[00:39:06] And if you think it is not going to turn around and come for you at a certain point, you are you're deluded. I find that video so shocking to cheer on the murder of someone you do not know in the street. This for me was a nader. This was like, you better just turn around and start going up Portland because this is this is bad. And I think in a sense, not that we had more murder in the street, but we really did have
[00:39:35] a lot more death in the street and we can get to that. And I think it's all sort of part of the same. We are the champions here. And I realized that's a bit of a I didn't phrase that exactly well, but I'm sort of trying to creep toward 110 here. Yeah. Measure 110, which legalized all street drugs in. Oh, yeah. We should we should talk about it. Just really quickly, though, just one comment on that.
[00:40:01] It's really when you talk about stories like that and that and the kind of it's like the psychology of what we consider a sort of productive protest had devolved into essentially the psychology of a mob. Right. For sure. Yeah. These were mobs more than protests, you know, at times. Right. And that is there's a whole literature about sort of mobs and mob psychology. And that seems to be kind of what happens. Right.
[00:40:29] People lose any sense of their own individual agency and moral sense. And they become part of this collective mass. Right. That is. And they get swept up in it. I remember the first when I first went to Portland to start covering the protests, it was, I think, my second or first night there. So it was in July. And it was very, very, very hot in front of the federal building. I mean, fires. And it was it was very, very dramatic.
[00:40:56] And there was a young girl standing next to me with her friend. And I could tell she was scared. And I think she she said something like, I don't really want to go in there. And I was like, you don't have to. Like people get swept up in this because it feels they're feeling something. I it's like epiphanic. But also she I had more kind of respect for her to say, I don't think this is a great idea. And kind of like dipped. Yeah.
[00:41:25] And just just just to just to close this out. Some of your reporting is so funny. I don't know if you mean it to be funny or not, but it just cracks me up. It's a serious topic. This is you're quoting a resident talking about some of the pointless vandalism back then. And and this guy says, I go in next door and I'm seeing things like people have insurance. Things are less important than lives. And then someone at the dog park told him he should factor in, quote, the decades and centuries of oppression and understand why people are doing what they're doing.
[00:41:54] I mean, so, yeah, it's the mob, but it's like actually people having what they think are rational discussions, you know, on next door or at the dog park. And the reasoning and the thinking is just so utterly stupid. Like it's just I mean, anyway, I was just struck by by some of that. And I'm not really sure that things have improved terribly since then, because I think, you know, we're tribal like people are either Democrats or they're Republicans these days.
[00:42:23] And if you're a Republican, you think the way Republicans do, because that's how Republicans think. And if Trump changes his mind, then you're going to change your mind, too. And and the same thing kind of happens on the left. Right. Like we're people aren't taught or encouraged to be independent thinkers. And especially when somebody like David Shore, that political researcher who loses his job in 2020, basically saying, hey, violent protests maybe don't work based on the research.
[00:42:51] You know, other people look at that and they go, well, do I really want to stick my neck out if you got to pay the rent? Right. I mean, it's it's a real thing. Looting is good, right? Right. It makes it come on where, you know, I. It's so bourgeois, some of these things, and it's like you can you can say these things from your little perch of comfort.
[00:43:14] We had this happen a couple of weeks ago, the New York Times conversation, you know, between Gia Tolentino and and saying, like, just Hassan. I find him one of the most loathsome characters that I can current in the current scene. But yeah, micro looting is good. Ha ha ha. I live in a two mile and a dollar house. I shoplift lemons from Whole Foods. It's like I shoplifted lip gloss when I was 13 and then got it out of my system.
[00:43:43] Get it together, lady. Be an example. Grow up. Grow up. Portland was a city of children for a long time. And then the people that weren't children just shut their mouths because they didn't want to they don't want to deal with it. They wanted to take care of stuff and just like pretend this wasn't happening and there was a pandemic going on. And please, please don't make it worse. And the kids are like, no, we don't make it worse. Yeah. Let's let's get let's let's get to measure 110 because right in 2020.
[00:44:10] voters in Oregon, by a by a large majority vote to decriminalize drug use, right? Hard use of hard drugs. Right. And and and there's a D.A. that's elected in Portland, Mike Schmidt. Right. Right. Right. Right. Before that or right around then, too. And he's a kind of progressive sort of sort of Soros kind of type D.A. Yeah. Yeah. Yeah. Yeah. So so so what was the impact of that, Nancy?
[00:44:39] And how do you see that fitting into this story? Well, interestingly, so measure 110 was already sort of unrolling even before Schmidt was elected, but he was for it. But but interestingly, he was elected and he wasn't supposed to take office. I don't think until November. But the guy that was there before was like, hey, with all the stuff that was going on, which was summer 2020, he's like, I'm going to leave early. You're going to take this over. This could be your problem.
[00:45:04] Schmidt was very, very he's a real true believer of the Soros or really Soros's son, Alex Soros, really like criminal justice. Let's get most of the jails. Like I am, too, for criminal justice. I want fair trials. I want I don't want people over incarcerated. I certainly don't want them incarcerated for smoking a joint. But we do have a criminal justice system for a reason.
[00:45:32] So measure 110 passes pretty handily. And what didn't happen was the trigger was not pulled on the money for treatment. OK, so all of a sudden you legalize for street use any kind of drug, you know, heroin and fentanyl and crack and pot and whatever else you want. And that's legal. Oh, but all that money for treatment that nothing happens.
[00:45:58] So people just start actually dying on the streets in downtown Portland. I mean, there were, I think, nine or 11 overdoses in a two block radius down by where Nordstrom Rack used to be. This is in a 24 hour period. Everybody's walking around carrying Narcan. I met a guy who was like a 70 year old guy, haberdashery guy by Broadway. He's like, I carry Narcan now because people are constantly falling down, overdosing on the street in front of me.
[00:46:28] The overdose rate is insane. We are not putting in people in jail because you can't. I remember walking by a really nice kind of brownstone building near PSU. And these two kids sitting there with their skateboards. Usually you thought they'd be blowing a joint. No, they were they were shooting up right there. I saw the city start to deteriorate.
[00:46:48] First, you had the punch in the eye from all of the destruction in downtown during a closed businesses because of the pandemic and then closed businesses because of the riots. And right on the heels of that, you get downtown really becoming, I'm sorry, like a zombie land of people using heavy, heavy duty drugs. What happened to Portland? Portland, it lost population for the first time in a very, very long time.
[00:47:16] I think at one point, like 40 percent of the of business rentals were open. I phrased that wrong. I'm not sure what the word, the proper wording is. But downtown became extremely depressed, compounded by city employees telling the mayor's office, we don't want to come back downtown because, you know, we like working at home now. And they're like, get your asses in here because we need to populate this downtown again.
[00:47:45] And it hasn't Portland has not sprung back. They did rescind 110 last year or in 2024. When did they take it back? 2024, I guess. But a lot of the damage is done to the city. The city, I think, kind of committed a sort of a semi-suicide with allowing a lot of this stuff going on. And from what I understand, and you guys probably know more about this than I do, but they still can't get out of their own way.
[00:48:15] They've got a very, very DSA-friendly city council. They still want a lot of the things that they wanted before. There's still a lot of calling out of racism and you're being mean to people if you put them in jail. I wrote an article a couple of years ago about a woman that was murdered in Portland in front of her children by her common law husband who had been arrested three times by the police for threatening to kill his wife,
[00:48:41] for strangling her for hours and telling her, I am going to kill you. And then getting arrested, they put an ankle monitor on him. And he said, I am going to kill her. They wouldn't keep him in jail. He got out and he killed her. That was under Mike Schmidt. And I think that Portland, I wrote a long piece, it's over on my substack called The Gloss of Good Intentions. Portland believed, they needed to believe that they were being the good people.
[00:49:10] And in order to be the good people, you needed to right all of the historical wrongs. And if that meant not jailing the, I believe the person I was writing about who killed his wife, I can't remember if he was Ethiopian or Sudanese, but he was Black. Like we cannot incarcerate people, especially not Black people. I mean, I get it. I get that you want to do a better job than historically people have done, just like we want to do a better job with women in sexual assault. But you have to look at what's in front of you.
[00:49:40] And that has not happened in Portland. I don't know if it's happening more now. But Portland, I truly believe, was a little city that could have been the next great American city. And it is not going to be that by its own hand. So Nancy, you also write about the ICE protests in Portland and what the Trump administration has been doing there.
[00:50:06] And so I wanted you to tell us a little bit about the ways in which you think the Trump administration and the right in America has also lost its mind, I guess. I mean, I was here in New York and everyone's like, Nancy, Nancy, ICE, you got to come. You know, I'd gone to the ICE protest in L.A. in June, covered that for Reason magazine. And I was like going back to Portland to report. I was actually in Portland last week, but I'm not reporting.
[00:50:36] And I saw what was going on in front of the ICE building. I had one friend who's pretty right wing and covering it. And she's like, it's pretty bad. I was like, is it? Talked to other people. They're like, not really. So let me get out there. So I go in front of the ICE building. There's like 25 people out there. Hello. When you've been standing in protests with 2000 people and everyone's getting tear gasped, it's, you know. But I said, OK, let me cover it. And, you know, how do I say this?
[00:51:04] Was the right using it as a photo opportunity? Yes. Oh, a thousand times. Yes. They were like, you know, photographing like the worst. My big story, which I'm never not going to be angry about. Never, never, never, never. And I want to bring up his name as many times as I can. I'm there. There's like 20 people there. And some guy gets a little American flag and he sets it on fire. Not a big one. I mean, seeing a flag on fire at protest is like seeing a bird in the sky. Like it's nothing. Right.
[00:51:34] But I'm standing there and this guy runs up and stamps out the fire. It was so boring. I didn't even shoot it. I was standing immediately there. OK, the guy that stamped out the fire is a is a independent journalist named Nick Sartor. He is apparently arrested a little later on, probably for taking the guy's flag because you're not supposed to steal other people's stuff, even if it's on fire, which is not illegal. Right. Right. So he gets arrested.
[00:52:03] He's released. Oh, it turns out that the next day, Pam Bondi, then the attorney general of the United States, says they are going to open an investigation of the entire Portland Police Department because of his being arrested. And she calls him personally. She calls him and says, I'm so sorry. So I wrote for a reason. Did she make him some milk and cookies, too? Because I got to tell you, man, I have been tear gassed to within an inch of my life. No one.
[00:52:32] I didn't get a call from the attorney general. Meanwhile, meanwhile, three days or four days later, he's at the White House, one of like six or seven people. Heroes, heroes fighting, you know, for the rights of ICE to stand there and whatever. And people dressed in cartoon frog costumes trying to get their attention. And he brings he brings the burnt flag to Trump as an offering like a dog laying a rat at his master's feet.
[00:53:02] I find him to be. And and I talked to my friend, the pretty right wing one, and she also agreed this was bullshit. And she said they've got a direct line. The White House is using these useful idiots to make it look like, you know, there's a terrible conflagration. You know, Karen Emmergut, who was the federal judge, she said, you can't come in here. Trump says, oh, can't call in the Oregon National Guard. OK, I'll call in the ones from Texas and California. They're like, no, you can't have our National Guard. Trump finally left.
[00:53:31] You know, he did the same thing in L.A. He expected L.A. If any city is going to burn itself down, it's going to be L.A., right? I've been there for some of those fires. But no, they chased him out. He just is looking to get purchased to say that he is right, that immigrants are burning down everything. And our entire country is at jeopardy because of that. It is not true, at least in the case of Portland.
[00:53:54] I will also say I was tear gassed there worse than I've ever been tear gassed at close range for absolutely nothing. We were there about six of us standing there. We weren't. Nothing was happening. All of a sudden, ice kind of things. And I hear click, click. I'm like, what? And all of a sudden, these like plumes of purple and pink. And I'm laughing. I'm talking to someone next to me. I'm like, oh, what is Taylor Swift going to like walk out of here? And then all of a sudden we were destroyed.
[00:54:23] Serious military greed, tear gasp. And it was set off for nothing. So do not tell me, ICE, that you are protecting the people of Portland from the terrible and dangerous immigrants. You are not. Is it still going on there? Yes. Is it still small? Yes. So that is my experience lately with ICE. I got to tell you, I do not have a lot of respect for how the Trump administration has handled this at all.
[00:54:50] I'm glad to see that certain people, Kristi Noem, one of them, were camped because they were carrying water for a bullshit mission. And I'm glad to see that. I mean, it's not over, but that part of it's over for now. Yeah. I mean, people have a right to protest, right? And when these protests started outside the ICE place and there's people in funny costume.
[00:55:12] I actually think that the vibe of those protests, at least from what I could discern from my perch in Seattle, was really, you know, at least some of the protesters has learned a lesson about what went wrong in the 2020, 2021 period. And they were using humor rather than violence to kind of make a point, which they have every right to do. And then for these righties to hop on that to try to create some kind of false narrative of what's going on. It's transparently bullshit.
[00:55:42] And it was the real sort of like keep Portland weird and funny, right? But I will tell you, will there be some violent protesters within there? Sure. Of course, there's going to be. Of course, there's going to be yahoos. There always will be. Is it the case that you will get people telling you they will swear on their mother's life that every single person in those costumes is a hardcore Antifa terrorist? Yes. I'm like, OK, try. Try again. Yeah. Last question, Nancy.
[00:56:10] Just about where the vibe of the city is right now, right? Because you've been there recently. And look, I was there December of 22. I was staying in downtown Portland for after the elections in 22. And downtown Portland was still in pretty bad way back then. Like a lot of not much activity, a lot of boarded up stuff downtown.
[00:56:32] The density of people who are mentally ill or clearly like tweaking on meth or, you know, out of their gourd on fentanyl or whatever was what's high. Right. Higher than in Seattle, which is saying something. Right. And and yeah, you know, my son goes to read now. So I'm down in Portland every once in a while. And it does feel like it's better to me, at least that it's better than it was. There's been at least some, you know, they did roll back measure 110.
[00:56:58] And it's not clear how effective some of their interventions are on some drug stuff. At least they're trying some stuff like to be a little different. But anyway, what's your take on kind of where it is now when you're in Portland? It's definitely lifted a bit since, you know, 2021, 2022. My sense is that it is still it's it's lost its its zing. You know, it could be the case, you know, cities have characters.
[00:57:27] Not that the characters can't change. But, you know, you think of a New York or you think of a London. You know, when my when my husband said Portland was not the horrible, depressed city it was in the 70s and 80s. Because, you know, maybe it's sort of resuming some of its original shape. I have friends there who own businesses who have told me they kind of want to get out. I met some people when I was there last week that I didn't know saying, yeah, we're kind of looking to move. It just doesn't feel like it's on the up anymore.
[00:57:56] Now, will it revivify and become something else? Yes, I think that's probably inevitable, right? Things things change and roll. And I hope it does. Because I get accused of being like a real naysayer about Portland. And I do have bad things to say about Portland. But I do wish good things for the city because it's a beautiful city. Food can be great. You can grow anything. And, you know, why would I not want it to to fly again? So let's see. Nancy Rommelman, thank you so much for joining us.
[00:58:26] Thank you so much for having me, guys. Nancy, thank you. That was great. That's it for another edition of Blue City Blues. I'm David Hyde with Sandeep Kaushik. Our editor is Quinn Waller. And thanks, everybody, so much for listening.