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On November 6, 2016, Justin Townes Earle made an important proclamation: He was moving to Portland.

“Another new town another new home,” he declared on Twitter, just two days before the Presidential election. “Northwest growing on me. I like this rainy motherfucker!”

Over the previous decade, the folk-roots singer-songwriter Justin Townes Earle had developed a loud reputation. He was the tall, tattooed, blustery troubadour who’d overcome the pressure and pain of being the son of country legend Steve Earle, moved to New York City at the height of his rise in the late 2000s, and since had established himself as one of the forebears of contemporary Americana music with records like Harlem River Blues.

Justin’s time in Portland was one of the most pivotal periods of his life: It was where, as a man in his mid-30s, he started a family and where he wrote his triumphant album, 2019’s The Saint of Lost Causes. It was also roughly the longest period—and, geographically, the farthest—that he ever lived away from his hometown of Nashville. But over his brief period in town (just a bit over two years), Portland would also end up becoming the setting for Justin’s full-blown relapse into substance use.

“He liked Portland and some of the things that, legally, Portland had to offer,” as one of Justin’s oldest friends once put it. It was the last place he lived before temporarily relocating, under difficult circumstances, back to Nashville, where he was eventually found dead in a temporary apartment from a fentanyl overdose in 2020.

But back in the fall of 2016, on the precipice of moving, Justin was at an exciting crossroads. In 2015, he’d fled the trappings of Nashville with his wife Jenn Marie Earle, spending that year in a remote seaside village in Northern California. He’d sought solitude far from home on the West Coast, where he was seldom recognized in coffee shops the way he was back in Tennessee. Then, in the fall of 2016, the couple received life-changing news that filled them with joy and also precipitated their move: They were going to be parents.

The decision was mostly practical. After a year in rural California, Justin knew he’d be revving up his touring. Driving over three hours to an airport every time he needed to fly to a gig wasn’t feasible. “We needed to move to a place that was better in reach to hospitals and things like that,” Justin told journalist Brian Wise in 2017. “The choices where we were were either San Francisco or Portland, and nobody can afford to live in San Francisco.”

Justin and Jenn Marie began settling into their first place in Portland, an old, spacious house on Imperial Avenue in Laurelhurst. Justin told his wife it was the nicest home he’d ever lived in. Justin started exploring the city, finding his favorite places to eat and spend money: They’d get dinner at Pok Pok, shop at Hollywood Vintage, and take long neighborhood walks to City State Diner for brunch or Staccato Gelato for dessert. But as they prepared to have their daughter, they mostly spent their first six months in town nesting. One of their favorite places to go together was the local hardware store.

Justin under which Portland bridge? JOSHUA BLACK WILKINS

“He’d say, ‘This is the first time in my life I was happy to be home,’” Jenn Marie remembered. “And I’d say, ‘You’re learning how to be home.’ It was kind of a joke, but it was a real thing: He was learning how to not be on the road. To do laundry, to have breakfast, lunch, and dinner, and sleep normal hours.”

Justin’s move to Portland was encouraged by a few friends in town. One was Josh Taylor. As owner of Oregon’s Cannabis Concierge, Taylor was known by just about every touring band in the country. He’d grown close with Justin over the years, even serving on and off as Justin’s touring manager throughout the 2010s. Justin, Taylor recalled, told him that Portland had always felt like a second home.

Then there was Andy Moore, Justin’s old friend and bandmate from Nashville. The two old friends—both Nashvillians new to town—began exploring the city together. Frank’s Noodle House was a Justin favorite dating back to his touring days. The Iron Horse out in Sellwood reminded them of a beloved Mexican restaurant back in Nashville. They went to Full Moon Thai, where Justin favored the pad kee mao, or Blind Onion Pizza, where he ordered the barbecue chicken pie. They wandered around, two old friends 2,000 miles away from their hometown, and had long, self-reflective talks about their dads, their new phases of life, and how far they’d come as adults.

“There is a sober and well-adjusted Justin that I know to have had some of the deepest and most heartfelt conversations,” Moore told Rolling Stone in 2020. “We talked about the shortcomings of our own families and paternal lines and ‘How are we going to be better than [them].’”

Justin’s first full year in Portland, 2017, was busy. He released his album Kids in the Street and spent much of the year touring in support of the record (that March, he had a residency at the original Doug Fir). He wanted to make as much money on the road as he could before his daughter, Etta St. James Earle, was born that June. In October, during a brief period at home in Portland, Justin showed up and sang a gorgeous cover of Paul Simon’s “Graceland” at a benefit show for refugees with his father, Emmylou Harris, Dave Matthews, and Brandi Carlile at the Aladdin Theater.

But Justin also spent quite a bit of his 2017 in the basement of his home on Imperial Avenue, where he was working on what would end up becoming his final album. Like many Americans, Justin was animated following the 2016 election of Donald Trump. He started tweeting at and about the administration. He described then-attorney general Jeff Sessions as “part time garden gnome and full time Confederate memorial.” He quoted a Mother Jones saying that also became his personal email signature: “Pray for the dead, fight like hell for the living.” And he tweeted in support of left-wing protestors countering far-right violence with violence: “I deeply truly believe,” Justin wrote that August, “that there is nothing wrong with putting some needle dick Nazi fuck on his ass. Fuck ‘em!”

All of this found its way into his music. The songs Justin began drafting for The Saint of Lost Causes were unlike anything he’d written. They were topically minded, Woody Guthrie-inspired third-person tales of social strife and economic alienation: the stories of someone living through the recent Flint water crisis, a ballad about a man who grows up in the housing projects of South Central Los Angeles, the tale of an Appalachian criminal whose life was destroyed by the raging opioid crisis.

“I feel that we’re in a place in the world…where we have been marginalizing people for such a long time that we’re going to find that they are going to strike back at us,” Justin told the Australian magazine Scenestr upon the album’s release. “And we’re not gonna like it.”

Those songs marked a new creative highpoint for Justin, but they also documented his own increased suffering. He began self-isolating, locking himself in his basement office, or leaving home to court trouble. Oftentimes, his destination was Chopsticks, the karaoke dive bar a stone’s throw from his Laurelhurst home that quickly became the locus for Justin’s substance use.

Justin had loved Portland from the moment he started touring as a solo artist in the late 2000s, but his history with the town had long been troubled. Justin once told a reporter that it was in Portland that he broke the only truly sustained sobriety of his life. At that point, he’d been devoted to twelve-step recovery and refrained from anything stronger than a cigarette for over four years. But, as Justin put it to journalist Chris Talbott in 2011, he “relapsed” on marijuana at a Portland festival (almost certainly Pickathon, where he played that year) in August 2008.

Those around him could begin to feel the city’s negative influence. “It wasn’t a good place for him,” said Jenn Marie. “There were bars on every corner, there were drugs everywhere. It was where things really picked up.”

The last few years of Justin’s life would be filled with turmoil and tragedy. There would be increased struggles with mental health and addiction. There would be violence: Justin was charged in June 2018 with fourth-degree assault in a domestic violence case after swinging his arms at his wife (despite there being documented evidence of Justin’s assault, the charges were dropped after he went to rehab). There would be a few isolated happy memories still to come, like when, in the fall of 2018, after rehab and his final recording session, Justin played back mixes for Etta and Jenn Marie of The Saint of Lost Causes (“He was so proud of them,” said Jenn Marie).

But there would ultimately be increased distance between Justin and his family. Justin relocated back to Nashville in 2019, a move Jenn Marie hoped and believed would be temporary. “We won’t stay there forever,” Justin said of Portland to journalist Joanne Will in 2017, back when Justin had his mind set on raising his daughter in New York. “Not that there’s anything wrong with [Portland], there’s just a little bit more culture needed for me to want to raise a kid there.”

Justin lived in town for little more than two years, and for much of that time he was on the road. But just as the city shaped him during that time, Justin also left a mark on his adopted hometown. When he died in 2020, Patterson Hood of Drive-By Truckers, another native Southerner making Portland home, wrote a song about the man he so wished he’d been able to spend more time with. It was called “We will never wake you up in the morning.”

“Hearts broken by your actions,” Hood wrote. “But you had the best intentions.”

When Jenn Marie thought back on her time with Justin in Portland, she tried to focus on when they first arrived. It was when their future as parents was in front of them, when their new surroundings provided a source of energy and excitement towards their uncertain yet hopeful future.

“Portland was great for six months, until it wasn’t,” Jenn Marie said. “Those were the last moments of just real life together, when we were really working as a complete team, and there were no secrets, and it was all for this dream together…. We had a wonderful time there before it went crumbling.”

Jonathan Bernstein is the author of What Do You When You're Lonesome: The Authorized Biography of Rolling Stone. He is a writer and fact-checker at Rolling Stone.