Portland Still Has an ADA Lawsuit to Adhere to
The city has removed as many as 50,000 tents in the last year, costing tax payers $16 million - so why are there still tents everywhere?
As 2025 approaches the end of its first quarter, Portland has been bombarded with negative news from every possible direction these days. There was a modicum of hope (not from me, of course, or many who actually closely follow the news or the writing on the city’s graffiti-smeared walls) citywide after the local elections ushered in an almost entirely new government. The city council elected eleven new members (after the city went to district representation and increased city council members from four to twelve), a new mayor, as well as three new county council members, leaving only three remaining members of city leadership from just a few months ago. After it appeared that former city councilman, Rene Gonzalez, looked to be a shoo-in as the new mayor a mere three months prior to the November election, a relative unknown, Keith Wilson, a local businessman and progressive, swept in and took the election instead, entirely backed by his bold claim that he could solve the city’s homelessness problem in one calendar year.
Obviously, Portlanders bought into Wilson’s positivity and affability. I was more than skeptical. I had met the man at a meeting in the Lents neighborhood four years previously when he had decided to try his hand at politics by running for a seat on the city council. Again, Wilson came across as a “nice guy” but he seemed both naïve and uninformed. For example, he had no clue what the Boise v. Marin decision was and why it was hand-cuffing the city, as well as others in the Ninth District, in its response to homelessness.
No mind, perhaps Wilson is a quick study. Part of his charm came from his aw-shucks personality, and his story of his hard-scrabble childhood, growing up in a large family in a small house in North Portland, pulling up his bootstraps, and owning a successful trucking company in Clackamas County.
I’ve often questioned the veracity of this story. In truth, Wilson’s father was the former president of the company Wilson ran before his election: Titan Freight Systems. How poor could his family have been?
Today is the Ides of March, so what better day to discuss the survival of a leader in politics. Wilson has to be honest with himself. He is most likely a one-term mayor unless he can make substantial improvements to the livability of a city that has always banked upon that very thing. Anyone who has lived in the city longer than a decade can remember visitors commenting about how safe and clean the city was, as well as the glowing reviews of the city from the New York Times and the New Yorker. If he can’t turn it around, he’s undoubtedly gone. And even more interesting is this: if he does turn it around, he’s going to have to piss off or outright alienate a good portion of the power-brokers in this city in order to do it (those being the greedy NGO’s and public unions which run this city).
I reached out to Wilson, and his office refused access to the mayor. This isn’t a particular surprise. PDX Real isn’t a member of the Portland Media Elite, even though across our half-dozen or so platforms, we get anywhere from 5 to 10 million impressions per month, and probably have better media coverage than any legacy media outfit in the state which is currently desperately holding onto their dwindling audience share. I did receive a rejection email from Wilson’s Press Officer Cody Bowman (he/him). I will get to this email later in this story, as well as another even more interesting email I received from the mayor’s office on the same day.
Undeterred, I decided to contact a man who may very well know more about the homeless crisis than Wilson does, John DiLorenzo. If you recall, DiLorenzo was the lead attorney who successfully sued the city for ADA (Americans with Disabilities Act) violations in May of 2023. The stipulations of the lawsuit were many, but mainly, under the terms of the lawsuit, the city was required to keep sidewalks and other walkways free of debris and homeless camps so the city’s disabled could use them safely. At the time of the lawsuit, then Mayor Ted Wheeler said that he had never been so happy to have been sued.
After nearly two years of the lawsuit being in place, I asked DiLorenzo how everything was going. First of all, I will state that DiLorenzo is a fan of Mayor Wilson. When I asked him if the mayor or any of the new city council members had reached out to him regarding the lawsuit, he said that he had not heard from any city council members, but he has been in regular communication with Wilson and others at the mayor’s office.
“Wilson and I have had several discussions about the lawsuit. He is very committed to keeping up his end of the agreement.” As a matter of fact, in the last year, the city has, “cleaned up around ten thousand encampments, and they have removed between 30,000 and 50,000 tents.” DiLorenzo told me. “The last fiscal year’s allocation for sweeping these encampments has cost the city $16 million, and Wilson wants to continue to do that. It’s so expensive because the workers who clear the encampments have to us Hazmat protocols, which cost around $150 per hour.”
I was rather amazed at the sheer number of camps and tents that had been cleared in the last year, and I told him so. I also asked him, if those numbers are accurate, why are we still seeing camps? “It’s simple,” said DiLorenzo. “JVP (County Commission Chair Jessica Vega-Pederson) and Field (Joint Office of Homeless Services Director Dan Field) are unwilling to hold distribution of tents and other supplies. The county and the Joint Office continue to pass out these supplies to their NGO network, which pass them out to the homeless. We won’t be able to make significant inroads in the problem until they support the city’s policies.”
In other words, the county and the Joint Office are passing out tents, tarps, and other supplies nearly as quickly as the city removes them. “The city needs to stop funding the Joint Office. We had the votes in the previous city council to leave the Joint Office, but Wilson reached out to Dan Ryan (the deciding vote and the only city councilmember who was going to continue with the new government) and asked him to defer the decision until the new government was in place. As you know, the new government will not vote to do that.”
DiLorenzo says that Vega-Pederson and Field are lost causes, but he thinks that Wilson believes that he can convince them both to change their course. Plus, Wilson knows that the county has most of the money to spend on the homelessness crisis. Without the county’s help, Wilson doesn’t have a chance. “The only way that things will change is if Vega-Pederson decides, at some point, to throw Dan Field under the bus for some reason. It’s very likely. She’s done it before with the health department and AMR (American Medical Response, Inc. – the company that provides ambulance services for the city).” A year ago, Vega-Pederson refused to follow suit with nearly every other elected leader and first responder in city who wanted to do away with the 2-paramedic policy, which many felt was the reason why the county’s emergency response time for ambulances was dangerously slow. Rather than changing the policy, which was well within her power, she instead blamed the issues on the individuals providing the service.
DiLorenzo says that Wilson knows that he can take the city back to court for its failures to keep the sidewalks clean, but, according to DiLorenzo, it’s not the mayor’s fault. “Wilson is looking into all sorts of solutions to various problems. I’ve spoken to both Wilson and the DA (new Multnomah County District Attorney Nathan Vasquez) about using civil forfeiture laws on drugs dealers to deter the drug dealing downtown.” According DiLorenzo, both Wilson and Vasquez are amenable to the possibility. “You take away these guys’ (drug dealers) cars and homes as a deterrent.”
“At this point,” DiLorenzo says, “I’m trying to figure out a way to sue the county.”
As of today, Wilson has less than 300 days to deliver on his promise that won him Portland’s mayoral seat. Have his efforts been successful? It’s difficult to tell. Anecdotally, there seems to be little difference in the homeless crisis since Wilson took over office. There had been some improvement in 2024, but this was well before Wilson took over the reins of the city. Wilson faces some troubling barriers in releasing his goals. First of all, the city is facing a $100 million budget shortfall. Even more concerning is the fact that Vega-Pederson announced last month that the county was going to have to cut 25% out of its homeless services budget, or $104 million, if other jurisdictions (the state, Metro, and potentially other counties) don’t kick in to help. Vega-Pederson said without additional funds coming in, the county might have to shutter some homeless shelters. Since Wilson’s homeless plan was to provide over 3000 available beds in the city for the city’s homeless, this is obviously a big blow to his plan.
Just last week, several media outlets reported on the resurgence of the downtown open-air drug market, an issue that the former mayor, Ted Wheeler, and the former city council put a great deal of energy towards dissolving, at which they were largely successful. As a matter of fact, the Portland Clinic had to shut its doors recently in the same area, citing safety issues in the neighborhood and the drug market that had sprung up at Yamhill and SW 13th. Wilson has never commented on this development.
Another significant concern is the new city council. While commissioners such as Kanal, Morillo, and Koyama-Lane seem more concerned about police attending their public meetings, they have not done anything meaningful in order to assist the mayor with his goals regarding homelessness. The only new shelter the city council has approved has been for illegal immigrants and refugees. It is also rather concerning that Mayor Wilson appears to hold little, if any, sway over his colleagues on city council. During the city council meetings, it is rare to hear the mayor speak up about any policy decisions the council is considering. This is a far cry from past mayors, who often were responsible for leading city council meetings, and often being deciding votes in important decisions. After a short honeymoon phase, Wilson’s influence is rapidly diminishing as well the good will from his commissioner colleagues. The only way that Wilson is going to be successful is if he takes a leadership role going forward, but this doesn’t seem be a strength Wilson possesses.
Now onto Cody Bowman (he/him)’s email to me when I requested an interview from the mayor. Here it is in its entirety:
Hi PDX real team,
Thank you for the opportunity to interview on this. We are consistently adding media interviews to the Mayor's calendar, and while we're unable to accommodate this opportunity, we appreciate the invitation.
In direct response to your question, the City declines to comment on the ADA lawsuit. Mayor Wilson's plan to address homelessness is guided by the ethos that Portlanders should be able to navigate our city safely, especially those who are mobility impaired. Mayor Keith Wilson is steadfast in enacting his ambitious plan to end unsheltered homelessness. This plan focuses on several key initiatives: prioritizing lifesaving nighttime emergency shelters, a path off the streets through day centers, and enforcing our existing laws on tents, trash, and unsafe RVs.
Mayor Wilson's blueprint to address the homelessness crisis is driven by the recognition that unsheltered homelessness is an emergency and must be treated as such. The plan includes setting up an incident command system to coordinate the work of government agencies and partners, led by Portland Solutions. This system taps into the expertise and infrastructure of the Portland Bureau of Emergency Management.
Portland Solutions is a system set up by Ted Wheeler in July of last year. It’s a centralized program hub to address the city’s homelessness and livability issues. It is supposed to bring several programs under one umbrella to increase service efficiency. That all sounds well and good, but in the above email, I don’t see any real solutions at all. Rather, all I read in this email is the typical politi-speak that one hears from many electeds who have nothing to really say.
Now, I come to the best part: the 2nd email from the mayor’s office, which undoubtedly went to thousands of others in the city. This email was about Portland Street Response and its newly expanded responsibilities. Although I’m not sure exactly what PSR really does for this city other than passing out cigarettes and granola bars to “the city’s most vulnerable,” at least now they “can now voluntarily shutter at-risk individuals to lifesaving shelter, day centers, addiction treatment facilities, and food pantries. These incredible, dedicated teams can now also enter certain public spaces like businesses and government buildings to help those in need.“
I guess we shall see how many of these homeless individuals will be willing to voluntarily get shuttled anywhere except where their next fix might be, which isn’t out of the realm of possibility considering the history of this organization. Wilson gushed glowingly about how great the PSR team is, and also congratulated his colleagues on the council, which is probably a good move for now.
“I’m grateful to our City Council, and their near-unanimous support for this move. Our shared win is a testament to how our new form of local government can deliver immediate, effective results. This new system of an executive Mayor paired with a professional city administrator has empowered our city to run faster, better, and at a lower cost.”
And then he further gushed, while giving a little subtle jab to the former government:
“Portland owes a great deal to those who had the courage to fight for the creation of Portland Street Response and shepherd it through uncertain times. We owe even more to our PSR teams, who do the hard and important work of helping our most vulnerable neighbors. To every person who has contributed to this extraordinary program, I say thank you for everything you’ve given to our city.”
When considering all of this lavish praise of PSR by the mayor, it makes me pause to think whether Wilson would dare to apply such praise to the emergency responders who do all of the heavy lifting in the city: Portland Fire & Rescue, and especially, the Portland Police Bureau. I wonder what commissioners Kanal, Morillo, and Koyama-Lane, who get “triggered” and seemingly lose control of all bladder functions at the mere sight of police officers, would think if Wilson glowed and gushed about Portland cops and their “incredible and dedicated teams?”
He would have a near council-wide mutiny, is what would happen.
Portland needed a special person in the mayoral office to lead the city back to greatness. A Bud Clark-type or even a hard-nosed Vera Katz would have sufficed. Instead, the city seems to be right back in 2018, at the dawn of our citywide crisis, when knee-jerk progressives such as Kafoury, Hardesty, and Eudaly were more concerned about micro-aggressions than solving the city’s emerging problems. Kanal, Morillo, and Koyama-Lane are deeply unserious people, and unfortunately, they are joined by at least a half-dozen others who have neither experience nor a clue how to steer the city towards invigoration and success.
I give Wilson a chance in a million. At least it’s a chance, right?
Move those tents into the bike lanes and they will all be gone tomorrow.
Once again, PDX Real comes through with the story no other outlet will touch.
The homeless crisis in Portland isn't letting up. If anything, it is getting worse. Here's how I know. We left our condo home in close-in NE Portland five years ago this week for my sister's place on the coast to reduce our pandemic risk. It worked. Once the COVID vaccine became widely available, we began returning to Portland about once a month. Coming back after being away for a while makes the changes that take place while you're absent more apparent.
What I saw in downtown Portland and inner Northeast and Southeast during our December 2024 visit made me think for the first time that the situation was hopeless.
Third Avenue between the Steel Bridge and Burnside looked like a zombie apocalypse. The amount of filth and the number of badly broken people in the street and congregating on the sidewalks were appalling. In other parts of town, I had to stop several times to avoid hitting walking blankets staggering under the influence of fentanyl. The tents and other makeshift shelters in the southeast industrial district gave the area the look and feel of a Brazilian favela. Downtown, the streets were practically deserted at mid-afternoon on a weekday. Security guards were present in force at a half-vacant Pioneer Place. For good measure, signs informed shoppers that dogs were on duty to detect firearms and keep visitors safe. The authorities' failure to shut down the open-air drug market close to the downtown Portland Clinic cost me my long relationship with a specialist who used to practice there and cost that specialist my business. There is no way I am going to spend an hour or more in the car to visit him at his new clinic in remote suburbia. Our condo building has been broken into enough times and some of the residents are so on edge that a neighbor who did not know me challenged me aggressively at the entrance from the outdoor parking lot. That was a heck of a note after the afternoon I'd had.
I feel a sense of despair every time I read a story in the newspaper with two names about yet another quagmire mayor Keith Wilson has stepped into voluntarily. The time Mayor Wilson wastes schmoozing with the front man for an anonymous contender for a Portland MLB franchise is time that Wilson isn't spending taking Jessica Vega Pederson and the JOHS to the woodshed for their obstructionism. I fear that Wilson's promise to get the homeless off the streets by 12/31/25 is going to end up like Tina Kotek's silly pledge to produce 36,000 new housing units per year. It ain't going to happen.
There is now a well established homeless underclass with its own norms and ways of coping in Portland that only Kevin Dahlgren seems willing to describe. The question isn't whether the city and county have sufficient funding to relieve Portland's hard-working voter-taxpayers of the terrible burden of having the feral homeless, the deeply addicted and the profoundly mentally ill living in our midst. The question is whether any of our elected officials have the slightest notion how to go about connecting with each and every damaged person who has found their way to the streets of Portland, assessing their willingness and ability to live like normal human beings and then applying the correct combination of resources to make that happen.
JVP and Dan Field are just whistling past the graveyard hoping that a majority of voters don't figure out that the homeless, addicts and mentally ill are here to stay.