Come to Portland, his sister said. It’s green and beautiful, people are friendly and there are plenty of jobs.

In 2018, Anthony Saldana took his sister’s advice. He left Las Vegas, where he was working in a casino, and moved to a Portland suburb.

He rented an apartment and got a job at Home Depot. Mr. Saldana, though, never quite found his footing. By early 2021, he was living in a tent, under a tree on the edge of a highway in Portland.

He wouldn’t let his sister, Kaythryn Richardson, visit him and shared only a few details with her about his life on the streets. He told her about the “bad people’‘ terrorizing him and about the Disney movies he had watched to drown out the chaos that was slowly pulling him under.

“Hello sister,” he texted last October. “I’m hurting.”

All of Portland, it seems, has been trying to figure out what has been happening to people like Mr. Saldana, and to Portland itself.

This city of 635,000, home to the world’s largest bookstore and majestic views of snowcapped Mount Hood, has long grappled with homelessness. But during the pandemic this perennial problem turned into an especially desperate and sometimes deadly crisis that is dividing Portland over how to fix it.

While other cities in the West, like San Diego and Phoenix, face similar issues, the suffering on Portland’s streets has dealt a singular challenge to the city’s identity as a liberal bastion that prides itself on embracing transplants from across the country.

In 2022, Portland experienced a spate of homicides and other violence involving homeless victims that rattled many in the community: a 42-year-old homeless woman shot in the face by two teenagers who were hunting rats with a pellet gun; a 26-year-old homeless woman stabbed in the chest outside her tent; another homeless woman, 31, fatally shot at close range by a stranger.

The search for answers points in many directions — to city and county officials who allowed tents on the streets because the government had little to offer in the way of housing, to Oregon voters who backed decriminalizing hard drugs and to the unrest that rocked Portland in 2020 and left raw scars.

But what has turbocharged the city’s troubles in recent years is fentanyl, the deadly synthetic drug, which has transformed long standing problems into a profound test of the Portland ethos.

Outreach workers in Portland say rampant fentanyl use, has coincided with the increasing turmoil among many homeless residents.

Doctors who care for people living on the streets say fentanyl addiction is proving harder to treat than many other dependencies.

Yet, as they have for years, legions of volunteers — professionals, recovering addicts and anarchists — routinely hand out sandwiches, wound kits and clementines around the encampments. Those volunteers include people like Jakob Hollenbeck, 23, who last year befriended a group camped out across the street from his house in Portland’s upscale Pearl District.

One of the tent dwellers was Mr. Saldana.

Mr. Hollenbeck, a recent college graduate, tried to help Mr. Saldana, 54, get back on his feet by giving him food, money and camping supplies.

And as he learned the roots of Mr. Saldana’s struggles, Mr. Hollenbeck became even more determined to help him.

“We are failing our unhoused neighbors every day,” Mr. Hollenbeck said. “And it’s something we can fix.”

‘Everything Just Seemed To Work’

Josh Alpert had a similar can-do attitude when he moved to Portland in the 1990s.

Mr. Alpert found an intense sense of community and “pride of place” among the many other transplants he met there.

“There was a sense that we are this Western city marching to our own drummer,” said Mr. Alpert, who grew up in Pittsburgh and, after coming to Portland, quickly decided he wanted to go into government.

This vibrant civic life played out while the city’s economy was growing and tourists were flocking to landmarks like Powell’s City of Books, the nation’s largest free-standing bookstore.

“Everything just seemed to work,” said Mr. Alpert, who worked for former Mayor Charlie Hales, from 2013 to 2016, including as his chief of staff.

Then came the tents.

At first, many were concentrated downtown and a few others were scattered across the city. Some of the early tent dwellers arrived with the Occupy movement in 2011, which involved camping in public spaces across the United States to protest income inequality.

“Occupy sent the message to the houseless that it’s OK to come out of the corners and be visible,” Mr. Alpert said.

The protests ended, but Mr. Alpert said many of the Occupy activists stayed in tents “because they had nowhere to go.”

The city’s popularity as a destination for transplants was helping to push rents beyond the reach of people who lacked a financial safety net, and forcing some of them onto the streets.

As the city’s point person on homelessness, Mr. Alpert supported new approaches to the housing shortage like the creation of temporary “villages” that could be run by homeless people themselves.

Instead of tents spread throughout the city, the villages, with names like Hazelnut Grove, were meant to be self-governing communities that empowered their residents.

“There was such a vital energy in the houseless community back then,” said Vahid Brown, who has worked with the homeless population for many years and was involved in the “village movement.”

Today, there are an estimated 6,300 homeless people in Multnomah County, which includes Portland. Only a relatively small number of them are still living in the homeless-run villages. Many live in tents under bridges, behind a hospital and in pine-scented groves. Some have fire pits. One has an American flag out front. A wheelchair. A library. A dead rat.

Mr. Alpert, who left government in 2016, says he has been blamed for allowing the tents to spread early on. “I wrestle even still with whether it was fair or unfair criticism,” he said.

Within a few years, the tents became more entrenched. In 2018, the federal appeals court that covers Oregon and much of the West ruled that cities could not prohibit people from sleeping outside if an alternative shelter wasn’t available.

Mr. Alpert still lives in Portland and likes to take long walks around the city. Over the past two years, he has seen at least 10 people overdosing, and has encountered a man walking around downtown naked and screaming.

“This is not the same issue that we were fighting,” he said. “This is something different.”

‘Love You, Sis’

When Anthony Saldana arrived in the city in 2018, he first rented his own place and then bunked with his sister and her partner, Phillip.

But Mr. Saldana just couldn’t make it work. As the pandemic wore into 2021, Mr. Saldana left his sister’s house and started sleeping outside.

He returned regularly for “Anthony Day” — Ms. Richardson’s day off from her job at a local grocery store. She served him meat lover’s pizza, while he did his laundry and took a shower.

In the morning, Mr. Saldana headed back to his tent.

He would say goodbye and leave. No hugs or even a fist bump. His sister said Mr. Saldana didn’t like to be touched.

Mr. Saldana was 4 years old when he went to live with a relative in California, who abused him until he was a teenager, his sister said.

Mr. Saldana was eventually diagnosed with depression, which he often tried to treat with alcohol and meth. While he was working for Home Depot, his sister said, the company gave him time off from work to attend a month of rehab.

Ms. Richardson said her brother wasn’t easy to be around when he was high and paranoid. But they all looked forward to Anthony Day.

“Thanks for dinner, it was awesome,” Mr. Saldana messaged after a visit in September. “Have a wonderful day. Love you sis.”

“You’re welcome,” Ms. Richardson wrote back. “Stay safe. Love you.”

2 Days, 7 Deadly Overdoses

The summer of 2020, after the killing of George Floyd, was a tumultuous time in many American cities, but particularly in Portland.

Protesters clashed with the police in the downtown streets from May through that fall, resulting in more than 1,000 arrests.

Sgt. Jerry Cioeta, of the Portland Police Bureau, worked 71 days with only three days off during the unrest. His hearing was damaged after an explosive thrown by a protester hit him in the hip.

After the street battles ended and Sergeant Cioeta resumed patrols, he soon found himself in a changed city.

In November 2020, amid the national reckoning over policing and criminal justice, Oregon voters by a wide margin approved a ballot measure that lowered the penalties for possessing small amounts of drugs like meth and opioids.

While an increasing number of states no longer criminally charge people for using marijuana, Oregon took the bold step of decriminalizing the possession of “hard drugs.”

When the police in Oregon see someone using these drugs, they can hand out a $100 ticket and a card listing a hotline for addiction treatment.

Known as Measure 110, the law was meant to focus the government’s efforts on treating addiction, not on arresting users.

At the same time, it allocated millions of dollars in additional funding for addiction services across Oregon. But the new money was slow to roll out.

Sergeant Cioeta, who oversees a bike squad that patrols downtown Portland, believes Measure 110 is fueling more drug use by sending the false message that “all drugs are legal.”

Others say that drug use has been common in Portland for decades and that Measure 110 has only brought the problem more out into the open.

Fentanyl was not a major focus of the discussions around decriminalization because it was not as widely used as it is now.

In 2020, the year voters approved the measure, 69 people in Multnomah County fatally overdosed from synthetic opioids, mainly fentanyl, according to the county health department.

Last year, such overdoses killed 209 people in the county, and the drug is smoked openly on Portland’s downtown streets.

Fifty times more powerful than heroin, fentanyl sets off a high that “human brains have never seen before,” said Dr. Andy Mendenhall, who runs Central City Concern, one of Portland’s largest nonprofit providers of mental health and homeless services.

“It makes it harder for folks to stay in recovery,” he said at a locally televised forum about addiction.

Fentanyl is often being used with other drugs, such as a synthetic form of meth, which outreach workers and the police say is also contributing to the increasingly volatile behavior on the streets.

Amid an outcry over Measure 110, the Oregon House recently passed a bill that would create stiffer consequences for possession of certain amounts of fentanyl.

Over two days in mid-May, seven people died of overdoses across Portland. One person died in a car, another in a tent and a third in a grassy area, three blocks from Powell’s City of Books.

‘He Wanted Me To Know’

When Jakob Hollenbeck graduated from the University of Oregon last year and moved to the Pearl District, a neighborhood of loft apartments and nice restaurants, he was keenly aware of Portland’s troubles.

Mr. Hollenbeck wasn’t afraid of the crime or homelessness, but he was upset with how the city was dealing with these issues.

Under Mayor Ted Wheeler, a Democrat, the city had been steadily stepping up the removal of tents and trying to move people into shelters.

But many of the people being displaced simply packed up their belongings and moved their tents to another patch of sidewalk.

Recognizing that many people struggling with addiction and mental illness do not want to live in a shelter, the Wheeler administration is developing several large encampment sites that will house people in “pods,” small basic structures with heating and air-conditioning units.

These pod clusters are different from many of the villages that sprung up a decade ago, because government contractors will supervise them.

“There is nothing humane about living outside in the elements, and I have sought to change that,” Mr. Wheeler said in an interview.

Preliminary results from a recent survey show that while the number of people who are homeless has risen, the portion who have been homeless for extended periods fell this year; officials said more people were also using shelters this year.

Mr. Hollenbeck, who is a believer in progressive approaches, said the city can only truly solve the problem by providing more affordable housing and mental health services. In the meantime, he said, citizens needed to step in to help their neighbors.

Mr. Hollenbeck raised $3,000 on GoFundMe to buy his neighbors camping supplies, and he borrowed his parents’ car to help Mr. Saldana relocate after his tent was taken down.

When Mr. Hollenbeck, a paralegal, learned that Mr. Saldana had been hit by a car, he helped prepare a lawsuit against the company that had insured the car involved in the accident.

Then, Mr. Saldana returned the favor.

One night last December, Mr. Hollenbeck was walking home with takeout when a man approached him and demanded his food. When Mr. Hollenbeck refused, the man brandished a shard of glass and said he was going to stab him.

Mr. Saldana and another man bounded out of their tents and stood between Mr. Hollenbeck and the man with the shard, who was also homeless. Mr. Saldana yelled at the man to leave, which he did.

“I don’t know what would have happened to me if he hadn’t done that,” said Mr. Hollenbeck, who was interviewed by local news outlets about Mr. Saldana’s courageous act.

A few weeks after the incident, Mr. Saldana told Mr. Hollenbeck about the abuse that he had suffered as a child and how it had shaped his life.

“He wanted me to know that’s why he lived on the street,” Mr. Hollenbeck recalled. “But he said he couldn’t do it much longer.”

‘People Act Like There’s Not Enough’

Just as Portland has attracted college-educated transplants, it has also offered respite to people from around the country who are living on the margins.

Kaetly and Irida Wren were unemployed and sleeping in their car in Memphis in the spring of 2021. Shunned by certain family members, the transgender couple saw few options in the South.

“Let’s go to Portland,” Kaetly remembers saying.

Kaetly, 21, was inspired by the city’s protests. An opioid user, she also heard that heroin was plentiful in Portland. Irida, 26, was told the city offered generous homeless services.

The couple packed up their Nissan Altima and made the 2,200-mile drive. They found support from social workers and groups like Street Roots, which publishes a newspaper focused on homeless issues.

On many nights, they stayed in shelters, but they said camping on the streets was easier.

Government data and interviews with homeless residents underscore Portland’s lure, far and wide. A Houston woman whose home was destroyed by Hurricane Harvey. A New Jersey activist who came for the Occupy protests more than a decade ago. A St. Louis woman who had been sexually abused by a relative.

The couple had hoped to find a sense of community in the encampments.

Instead, they encountered “infighting,” which they attributed partly to fentanyl.

The pull of the drug is so strong that many users are paranoid that supplies are running out, Kaetly said.

“People act like there is not enough of it on the streets for all of us. When in reality, there is more of it on the streets than there ever has been,” she said.

On the night of April 18, the couple were in their tent across from a church when a man slashed the side of the tent and attacked Irida with a knife.

She was stabbed six times in the torso and hands, according to the police report, and was “fainting” shortly after officers arrived on the scene.

They planned to head back to Tennessee last month. Portland “is definitely not what I expected,” Irida said.

Carrots or Sticks?

There are days when Portland is not what Jessie Burke, a co-owner of the Society Hotel, expected, either.

When a woman burst into her hotel lobby and wrestled with two employees. Or when she watched another tent dweller bang her head bloody against a storefront window.

Ms. Burke, who with her husband opened the boutique hotel in the Old Town neighborhood in 2015, believes that Portland can recover but that it needs to adjust its attitudes toward homelessness.

In recent years, she said, the city has been too permissive about camping and people using hard drugs in public places.

“Some people respond to carrots, and some respond to sticks,” Ms. Burke said. “But we have used carrots here.”

She is encouraged by the encampment removals, which have reduced the number of tents in the area around her hotel.

But she said government officials needed to compel more homeless people into mental health and addiction services.

“A lot of people say, ‘How do we get the old Portland back?’” Ms. Burke said. “I think we need to look at the lessons learned from this time and to get to something else.”

Anthony’s Day

While some debate the city’s future, Mr. Hollenbeck has been focused on the immediate needs of his homeless neighbors.

Before leaving for a trip in early March, Mr. Hollenbeck checked in on Mr. Saldana.

You need anything, Anthony?

When there was no answer from inside the tent, Mr. Hollenbeck figured his neighbor was sleeping.

Two weeks later, when Mr. Hollenbeck returned, there was still no sign of Mr. Saldana.

“Haven’t seen you around lately — hope you are good,” Mr. Hollenbeck wrote in an email to Mr. Saldana on April 13.

Five days later, the police received a call about a body found by a worker preparing to remove Mr. Saldana’s tent.

According to a police report, the body had been “unnoticed for several weeks,” and investigators struggled to identify him through fingerprints. Eventually, the police determined it was Mr. Saldana.

He died from a fentanyl overdose, his sister said.

Not long after his friend’s death, Mr. Hollenbeck got word that the insurance company was offering to compensate Mr. Saldana for the injuries he sustained when he was hit by the car.

He would have received $16,600, enough to cover many months of rent.

“The conditions that we have created as a society didn’t let me get that money to him in time,” Mr. Hollenbeck said. “That is something that haunts me.”

Ms. Richardson appreciates what Mr. Hollenbeck did to support and comfort her brother. And she will hold on to the image of her brother standing up to protect his young neighbor.

It was Portland at its best, and proof to her that the city’s ethos of community endures.

But in the end, that wasn’t enough to save her brother from the hurt that followed him wherever he went.

The last time she saw him was on Feb. 26 when he visited her house for an Anthony Day.

He hated having his picture taken, so when she saw him asleep in the living room that day, Ms. Richardson secretly snapped a photo.

He was stretched out on the couch, which was draped in a large blanket patterned like the American flag. His head rested where the stars and stripes came together.

Ms. Richardson posted the image on Facebook after his death. “I love you Anthony,” she wrote. “And know that you are now at peace.”