Think Out Loud

A reflection on homelessness in Portland, through the eyes of a housed neighbor

By Elizabeth Castillo (OPB)
Jan. 13, 2023 5:38 p.m. Updated: Jan. 20, 2023 5:31 p.m.

Broadcast: Friday, Jan. 13

Jakob Hollenbeck, left, reflects on Portland's policies regarding homelessness with "Think Out Loud" host Dave Miller. Hollenbeck, a housed Portlander, became friends with some of his neighbors experiencing homelessness. And over time, he says, they were forced to move.

Jakob Hollenbeck, left, reflects on Portland's policies regarding homelessness with "Think Out Loud" host Dave Miller. Hollenbeck, a housed Portlander, became friends with some of his neighbors experiencing homelessness. And over time, he says, they were forced to move.

Elizabeth Castillo / OPB


Jakob Hollenbeck moved from Eugene to Portland this past summer. While he witnessed homelessness in Eugene, and even wrote an opinion piece about it for his university, he was still surprised by what he saw in Portland. Over time, he became friends with some of his neighbors experiencing homelessness. They were ultimately forced to move, he says, after the city posted a notice for them to vacate the area. Hollenbeck says his neighbors deserved to stay. He joins us with more on his experiences and how he views Portland’s policies regarding homelessness.

Note: This transcript was computer generated and edited by a volunteer.

Dave Miller: This is Think Out Loud on OPB. I’m Dave Miller. We’re going to end today with one housed Portlander’s take on homelessness. Jakob Hollenbeck is a paralegal who moved to the city’s Pearl District this past summer. Starting in the fall, he became friends with some of the people who were camping on his block. They later defended him when another homeless person threatened to attack him, but then within a week those defenders were swept by the city. We met up with Jakob in downtown Portland yesterday afternoon to get his full story. I started by asking what he found when he arrived in Portland from Eugene in July.

Jakob Hollenbeck: I was used to the prevalence of homelessness in Eugene because it has one of the highest per capita rates of homelessness, but here it was just really close to me. If I walk even one block, I see countless people that are just on the streets unsheltered. And about September, people moved in directly across from my house on the sidewalk.

Miller: It’s not uncommon for people in Portland, probably people everywhere, who have homes or apartments to just try to pretend that homeless people don’t exist just to ignore them and walk by them. What did you do?

Hollenbeck: I wanted to make them feel welcome in the neighborhood. So  whenever I passed by I made sure to say hi, introduced myself, learned their names and gradually over time when I was going to the grocery store, passing by them, I asked them if they needed anything and got them some cold water during the pretty sweltering summer. We just kind of built a relationship from there.

Miller: How would you say? What was the relationship like?

Hollenbeck: I really enjoyed the people that lived there. They were all really sweet. They’re older gentlemen and they were just very, very funny and nice. And so it grew up, it grew into what I would call a pretty genuine friendship.

Miller: This was a group of older men who had arrived in a small encampment altogether. They had arrived as a group.

Hollenbeck: There was a core of around four of them that arrived together and then the others came in different waves. But yeah, they all seemed to know each other and get along well. It was really cool to see they had their own little community going on.

Miller: Do you know if others of your housed neighbors did the same thing by spending the time to talk and getting to know and building relationships with those men?

Hollenbeck: Yes. I actually have spoken to quite a few of my neighbors, I should say that the area where I live, there are only two triplexes on the street and that’s it. So I’ve spoken with all of my neighbors, I think, regarding those men. Maybe they didn’t become friends with them, but they were all friendly. They all knew names. They had all helped them out in some ways because they all saw the same thing that I did, that these were a really good group of guys, they were looking out for us. One of the neighbors actually even offered them a job at a steel mill because he just recognized that they were stand-up people.

Miller: How much did you talk to the men experiencing homelessness about the circumstances of their lives–how they ended up on your block?

Hollenbeck: That’s something I usually tried to avoid. Since talking with them for a long time, they’ve actually mentioned to me that it’s not something they usually like to talk about with people. So I’ve just kind of steered clear of that subject. I know, though, just from them telling stories about their lives that the vast majority of them were housed well into their forties. Some of them owned houses, some of them worked high paying jobs and through some variety of circumstances they ended up homeless and when you end up homeless, it’s really hard to get out. And so a lot of the gentlemen had been homeless for 10 years.

Miller: So let’s zoom forward to what happened almost exactly a month ago. It was a Monday evening in December.

Hollenbeck: I was coming back from getting some takeout at around 11 p.m., and there was an unhouse gentleman who had actually been helping.  He didn’t live on my street, but he lived really close and I had been helping him with the GoFundMe I had set up. I got him some boots and some other warm supplies and earlier that night I had made him dinner but when he saw me coming home with food, he stood in my way and told me to give it to him. I told him that I was planning on eating it and that I had just given him food a few hours ago and before I could even offer to share it, he grew really belligerent. He had a glass shard in his hand and he was about 10 feet away from me in the middle of the street. I was on the sidewalk, he was standing between me and my house and he grew really belligerent and said he was going to kill me.

Miller: What was going through your mind?

Hollenbeck: I was paralyzed. Yeah. I can’t really recall any thoughts, I just stood there, I didn’t really know what to do. I was just really, really fortunate that two of the gentlemen in the tent encampment jumped out of their tents and rushed in front of me.

Miller: What did they do?

Hollenbeck: They told him to leave me alone and that they weren’t going to let anything happen to me. And he didn’t immediately go away, but after some shouting back and forth, he started backing off and going back to where he lived, and I was able to go back home.

Miller: What kinds of conversations did you have with your friends, the men who were just right across from your home, after that?

Hollenbeck: Oh, I went over after work the next day and thanked them, brought them some food and let them know how much that really meant to me, because they didn’t have to do that. They could have just stayed in their tents. I don’t really want to think about what would have happened if they did that. And so I thank them profusely, and they told me that’s just how they were raised. One of the gentlemen, Anthony, told me that he was an ice hockey defender and he said that he wasn’t really good at scoring, so he knew he had to take a couple of hits for the team, and it was just a really profoundly sweet and humanizing thing to hear from someone.

Miller: You’d been threatened with a shard of glass, which could be used in a deadly way. Did you consider calling the police?


Hollenbeck:  I did. I knew that the man who attacked me had pretty severe mental health issues. I had spoken with him many times before this and he was actually a really sweet guy, but I had seen him go through mental health episodes. So I didn’t necessarily want to get the police involved for that reason because I want him to get help and I don’t think that he would find that in the prison system. But the real reason I didn’t call the police is because the gentlemen who protected me asked if I was comfortable with it to not call the police because they didn’t want to attract police presence to the area and get swept themselves.

Miller: It’s a really complicated situation that you’re describing.

Hollenbeck: Right.

Miller: I’m curious . . . Well, first of all, maybe you can take us through what happened after that. My understanding is that within a couple of days, the gentleman who lived right next to you saw a sign that said, “You have to leave this area, we’re going to sweep this area.” When did that happen?

Hollenbeck: Right. So I was attacked on Monday and by that Friday when I woke up, I saw that sign telling them that they had 72 hours to vacate the area.

At that point it’s a Friday, 72 hours is not work hours, it’s not work days. They had Saturday and Sunday and by the time Monday rolled around, they had to expect to be gone or have an encounter with the city and likely lose a lot of their stuff. So I spent that day trying to call everyone that I could. I called City Council members. I work in the legal area and I have quite a few connections to public interest attorneys so I contacted everyone I knew and they told me essentially that there is no remedy here. There is no process to get the city to reconsider the sweep. I tried organizing our neighbors, had them send in testimonials to the city sweep hotline but no one got back to us until it was too late.

Miller: So what happened?

Hollenbeck: On Sunday, they all decided that they wanted to leave so that they didn’t lose their things. Initially one of the gentlemen, Anthony–who protected me–wasn’t planning on using his tent. So I had, over the past couple of weeks and months, gotten him winter supplies, got him a tent, a sleeping bag, tarp and things like that. He told me that he felt warm for the first time since he had been unhoused. A few days later when the city posted that sign, he told me that he appreciated everything that I had done, but he was going to give me back the sleeping bag, he was going to wash it, give it back because he couldn’t do it anymore. He told me that he had been swept–this is his third time in six months and every time that he tries to establish himself and get stable, the city just comes and pushes him away–and he told me that he was just going to go sleep on a park bench where no one would bother him. And that really broke my heart because I really felt like I had been able to make a difference to bring some warm nights to people who hadn’t had that in years and the city undid that just like that. And so I talked with him over the next couple of days and convinced him that if I was able to get a car to transport them to a new area, that he would keep his things and that he would stay in a tent and stay warm at night. So that’s what we did on Sunday. I got a car from my parents and I brought  three of the gentlemen to a new area and helped them set up.

Honestly, I saw why he reacted the way he did. At first I thought maybe he was overreacting or wasn’t thinking straight, but it took me two trips with a pretty large car to be able to set them up. I can’t imagine trying to do that by hand. It’s about a 10-minute walk from my house where we ended up going. Just looking back on it, it would have been impossible to keep his stuff and set it up in a way that wasn’t a week’s worth of work.

Miller: I should say that we have met up and we’re now just about two blocks away from where you took them where you helped them to get set up which is in the southwest part of downtown, but they’re set up now right over 405. We had to walk two blocks away just to get a little bit away from the highway sound. Who chose that exact location?

Hollenbeck: I should say that I live right off of 405. It’s quieter where I am, but that’s the general location where we were. They had that spot in mind because–I don’t quite understand why—they like being near the highway. And they think that there’s space available near the highway. And they knew actually that people had been swept there earlier so this spot was vacant.

Miller: Vacant, but also a place that had already been perhaps prone to sweeps?

Hollenbeck: I don’t know if there’s an area that isn’t prone to sweeps.

Miller: In the big picture here, I’m curious what you do when you add all of this together because I mean there’s this story of human kindness and connection that you made and that was reciprocated. And that maybe saved your life or or or maybe prevented you from being really seriously hurt.

It’s also a story of another person experiencing homelessness who, as you say, it seems like he’s been dealing with some serious mental health issues, who seems like he was a very serious danger to you. How do you think about all of this together?

Hollenbeck: Well, I think that that experience, upon reflecting on it, I couldn’t really come away with any stigmas towards unhoused people because sure, an unhoused person attacked me, but two unhoused people protected me. And the image of the one unhoused person who attacked me is the image we see a lot when we watch the news and media. But there are so many, there are 5,000 people in the city experiencing homelessness—more than that–and if everyone was acting like that, one person who attacked me, it would be a completely different city.

The vast majority of people are just struggling to get by and the vast majority of people I’ve spoken with and interacted with have been just as kind, generous and gracious as the gentleman who protected me. So, I would say that the experience made me want for a better system to help the one unhoused person who attacked me but it also made me want for a better system to help the unhoused people who protected me.

Miller: Do you have an idea based on the conversations you’ve had with what those two better systems look like?  On the one hand, clearly you’re talking about at the very least very good mental health care. And then and then questions about how to help the many, many unsheltered people here. What are you advocating for?

Hollenbeck: Well, I think that the mayor has hidden behind the complexity and magnitude of the problem, saying that this plan that he has made to ban camping and have large sanctioned campsites may not be the greatest plan, but it’s the best of bad options. And that’s simply not true. We have a number of programs that have been tried across the country, and even in our city, that can get people into housing faster and cheaper than this current model. One of those projects is Project Turnkey that has been tried in post-COVID in Portland, repurposing motels, hotels, apartment complexes into housing that people can get into quickly. Other programs like Move-In Multnomah have paid landlords a year’s worth of rents to allow people to get directly off of the street and into housing and it doesn’t come with the 5 to 10 year wait time that a lot of the low income housing vouchers take. That program has been stopped because of how expensive it is. It costs, I believe, roughly $13,000 a year per person. But if we look at the mayor’s own plan, for three sanctioned house campsites that can hold up to 750 people, they’re budgeting up to $6.8 million. And if you do the math there, it works out to about $9,000 per year per person, not to house them, but to put them into large campsites when they were already camping.

So if we’re thinking about effective uses of money, we need to get people off of the street and into housing. Criminalizing homelessness essentially is only pushing people further and further into homelessness. The sweeps need to stop. I understand that if someone’s being dangerous, like the person who attacked me, that’s a different story, but the people who protected me had done nothing wrong. They swept our street; they picked up glass; they picked up cigarette butts; they were perfect neighbors. And on a whim the city was able to evict them on 72 hours notice and there was nothing that anyone could do, not even the people who lived on that street. There was no way for us to advocate for them to stay. And in the process, they had to start over. One of the guys told me that it was one of the spaces they had been the most stable and comfortable in 10 years of being homeless and that was taken away from them just completely on a whim. And so I want the city to start focusing on solutions that get people stable and not ones that push them deeper and deeper into homelessness.

Miller: We came here because we were hoping to talk with you and some of the men you become friends with when you went to their tents and they didn’t respond. They may not have been there. But do you plan to maintain–to keep up–friendships with them?

Hollenbeck: Yes, I have. I should also note that the week they were told to leave by the city was the week that the snowstorm happened. So they had to leave on a Monday and the snowstorm came on Wednesday, Thursday and Friday. So during that storm, I made sure to go there and make sure that they were okay. I brought them more supplies and I’ve been stopping by now and again since. I think it is something that’s really important–especially if you’re unhoused and you’re surrounded by people who outwardly look down on you and can oftentimes be really cruel to you–to know that there are people who care for you and welcome you and don’t hate you for just trying to exist on the street.

Miller: Jakob, thanks very much.

Hollenbeck: Thank you.

Miller: I talked to Jacob Hollenbeck yesterday afternoon in downtown Portland. Here’s a quick note about the numbers he mentioned near the end. After the interview, Jacob emailed us to say that according to recent reports by OPB and the Oregonian, Portland’s sanctioned campsites could cost up to $15,000 a year per person. The county’s Move-In Multnomah project is a little more expensive, over $16,000 a year, but he noted it provides actual homes.

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