GREENSBORO, N.C. — Months before he allegedly pointed a semiautomatic rifle into a Florida golf course as former president Trump approached, Ryan Routh described himself as a failure.

Nearing 60, he was running a small business building tiny homes and sheds in Hawaii. He had tried to reinvent himself by volunteering to fight in Ukraine but was rejected.

He had no assets, no retirement savings, no bank account, he wrote in an e-book describing his time in Ukraine that he predicted no one would read.

One topic that appeared to preoccupy him: political assassination. In his book, Routh repeatedly wondered why someone hadn’t killed Russian leader Vladimir Putin. And he said Iran should feel free to assassinate Trump.

“No one here in the US appears to have the balls to put natural selection to work or even unnatural selection,” he wrote.

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Routh’s long and strange journey from running a roofing company in North Carolina to what the FBI has called an apparent assassination attempt in Florida on Sunday left friends and acquaintances mystified. He could be odd, many of them said, and had a history of mostly minor run-ins with police, but wasn’t threatening.

“He was a little intense, but super nice,” said Tony Strader, Routh’s neighbor in the seaside community of Kaaawa, Hawaii.

Still, in recent years, there were hints of a kind of unraveling, particularly since he went to Ukraine in 2022. While Routh saw himself engaged in a Manichaean battle of good vs. evil, others found his activities there counterproductive and disturbing — so much so that they flagged him to U.S. government agencies, they said.

After returning home to Hawaii, he lashed out in unexpected ways. Saili Levi, a vanilla grower on Oahu, described a disconcerting experience last year after he paid Routh to build a trailer. Levi said the work was shoddy and he asked Routh to repair it or return his money. Routh refused and fired off an irate email. Routh wrote that he had traveled to Ukraine twice in support of “freedom, human rights and democracy around the world and I come back to bullshit such as this.”

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“Perhaps I would be happier dead on the front lines than dealing with rich people in fancy cars as I drive old broken-down vehicles and hoping to keep my account out of the negative and hoping for food to eat,” wrote Routh in the email, which Levi shared. “You disappoint me as a human.”

Routh, 58, appeared in court Monday for a hearing on two federal firearms charges. He remains in custody and has a detention hearing set for Sept. 23. Federal law enforcement officials have not yet identified a motive for his actions, and Routh’s lawyer declined to comment Tuesday.

To trace Routh’s path to West Palm Beach, The Washington Post interviewed nearly 20 people in the U.S. and Europe who knew him or had knowledge of moments in his life. Much of his journey remains unclear, including when he arrived in Florida, where he allegedly hid just outside Trump’s golf course for hours overnight. He fled without firing his weapon, authorities said, after the Secret Service spotted his rifle and shot at him.

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The portrait that emerges from Routh’s associates is of a man who spent much of his life in anonymity, only to seek purpose and attention in recent years in Ukraine, before seizing the most powerful spotlight possible in an apparent attempt to assassinate a presidential candidate.

Members of Routh’s family either declined to comment or did not respond to questions. His older son, Oran, told CNN that Routh was “a loving and caring father … it doesn’t sound like the man I know to do anything crazy, much less violent.”

‘A whole, live horse’

Routh was raised in a well-to-do subdivision of Greensboro, said Kimberly Hassler, a longtime family friend. His father was a chemist and his mother taught home economics, she said. Hassler remembered Routh as a friendly and energetic person who was generally more fun than his two siblings, who she said went on to become a lawyer and a banker.

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There was nothing out of the norm, Hassler said. “They were one of the closest families we knew,” she said. Hassler last saw Routh in 2021, when he returned to North Carolina from Hawaii to deliver a eulogy at his father’s funeral. He greeted her warmly.

In his book, Routh wrote that he was “kicked out and on my own” at the age of 16. He spent two semesters at North Carolina Agricultural and Technical State University in the mid-1990s but didn’t earn a degree, a university spokeswoman said.

An early brush with the authorities had Routh cast as a hero: in 1991, at the age of 25, he was featured in the Greensboro News and Record after he confronted and chased a rape suspect. The local chapter of a police association presented him with an award.

Over the years, he accumulated a lengthy list of minor offenses — writing worthless checks, failing to obtain a permit for construction work, engaging in welfare fraud, driving without a current inspection. But in 2002, his interactions with the authorities took a more serious turn.

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In April of that year, Routh was arrested for possessing an explosive device, according to Chris Parrish, the assistant district attorney of Guilford County. He was later convicted and sentenced to four days jail time. He was also required to complete a mental health assessment, Parrish said. (No further details of the case were available.)

Then, that December, Routh was stopped by Tracy Fulk, at the time a Greensboro police sergeant, for driving his pickup with a revoked driver’s license. She saw him reach for a duffel bag that contained a gun, she recalled in an interview, and pulled her own weapon.

Routh immediately drove off, she said, and barricaded himself inside his business, United Roofing. Police surrounded the premises and called in a SWAT team, Fulk said. After several hours, Routh emerged and was arrested. He pleaded guilty to carrying a concealed weapon and resisting an officer. He received probation and a suspended sentence, according to North Carolina Department of Corrections records.

After that, Routh continued to pop up in North Carolina case records — driving without insurance, failure to pay taxes — but was not arrested again until eight years later, in 2010. He pleaded guilty to theft after stealing two sinks and construction material, Parrish said, and was sentenced to probation.

Whatever his legal troubles, he appeared to be a good — if unconventional — neighbor. Kim Mungo lived next door to Routh and his daughter for nearly two decades on Hiatt Street in Greensboro and told reporters Monday that he had always been friendly to her.

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Mungo recalled a stretch during which Routh and his daughter kept a horse in the living room. “A whole, live horse,” she said. “It was crazy.”

Despite such eccentricities, the neighbors generally got along. “They were kind of weird. But they didn’t bother me, and I didn’t bother them,” Mungo said.

Routh sold the ramshackle house earlier this year for $170,000, a deal he negotiated from Hawaii. Todd Doerner, the new owner, described the home as uninhabitable and said he plans to tear it down. Doerner said that when he took possession of the property, there was no kitchen and no working bathroom.

One thing that did remain: multiple security cameras mounted around the exterior.

‘Something wasn’t 100 percent’

Around 2018, Routh moved to Hawaii, where he lived with a woman who described herself as his fiancée on a GoFundMe page. He started a small business building tiny homes and sheds. For two years, he volunteered his services with HomeAid Hawai’i, a nonprofit that combats homelessness. Kimo Carvalho, the group’s executive director, said in a statement that the group received no complaints about Routh.

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Apart from a few traffic violations, his run-ins with police appeared to lessen after his move to Hawaii. However, at one point in 2019, the FBI received a tip alleging that Routh possessed a firearm, something prohibited because of his criminal record. Jeffrey B. Veltri, the special agent in charge of the FBI’s Miami field office, said Monday that investigators interviewed the person who submitted the tip and passed the information to local law enforcement in Honolulu. The tip did not result in any charges.

Four years after Routh arrived in Oahu, however, the focus of his attention changed dramatically. After Russia invaded Ukraine in early 2022, Routh joined a flow of volunteers who wanted to support Ukraine’s war effort. While many had prior military experience, Routh had none. The international legion of Ukraine’s armed forces turned him down because of his age and inexperience, according to an interview Routh gave in 2022. Ukraine’s Ministry of Defense said Routh never served with its foreign volunteers.

Instead, Routh set up a tent in Kyiv’s central Independence Square and spent several weeks camped there before the structure was removed by police. He cut a distinctive figure: his hair was dyed yellow and blue, the colors of the Ukrainian flag, and he often wore a stars-and-stripes T-shirt.

He sought attention from foreign media as the war raged. Guillaume Ptak, a French freelance journalist, said that Routh approached him in June 2022 and asked to be filmed on Independence Square. In the video, Routh speaks in front of a display he created of 50 flags he said represented the nationalities of people who had volunteered to fight with Ukraine.

Routh appeared “gaunt, emaciated and seemed not to have been sleeping a lot,” Ptak said in an interview this week. His conversation was “all over the place.” Ptak found him “loopy but well-meaning.”

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A military medic from the United Kingdom, who spoke on the condition of anonymity because of the sensitivity of the subject, echoed that assessment. He met Routh three times in Kyiv.

“After a few minutes talking to him, you could tell that something wasn’t 100 percent,” the medic said. “But he seemed harmless.”

Others disagreed. Chelsea Walsh, a nurse from Florida, spent six weeks volunteering in Ukraine and said she met Routh there in May 2022.

The conflict attracted a range of Americans, Walsh said. Some of them were sincere while others were like Routh, she said, describing him as an opportunist. She said he was prone to sudden bursts of anger. Once, she saw him curse and kick a homeless man who asked for change. “He was very erratic,” Walsh said.

When Walsh returned to the U.S., she said, she spent an hour at the airport with Customs and Border Protection personnel detailing her concerns about several Americans in Ukraine she felt were dangerous. Routh was chief among them.

A spokesperson for CBP did not respond to a request for comment.

All told, Routh spent five months in Ukraine in 2022 and three months there last year, according to his account. His repeated efforts to recruit foreign fighters to Ukraine, particularly from Afghanistan, raised alarm bells in some quarters. In Kyiv, he was filmed wearing a T-shirt with his email and phone number, presenting himself as a military recruiter promising pay of “$1200.” In his book, Routh describes repeated and futile efforts to obtain visas for Afghan volunteers to travel to Ukraine. “Paperwork overrides the slaughter of humans every time,” he wrote bitterly.

For several Americans connected to aid efforts in Ukraine, Routh’s activities looked like possible human trafficking. There were also widespread concerns about Routh’s mental health, said Sarah Adams, a former CIA officer who helped run a network that linked 50 aid groups to share information and coordinate humanitarian efforts.

In June of last year, Adams put a warning about Routh on her network’s LinkedIn page telling people to beware of him and his recruitment scheme. Routh was instructing Afghans to travel illegally to Iran, she said, as a pathway toward joining the Ukrainian foreign legion. “This is a fraud,” she wrote. The same day, Adams said, a colleague forwarded the alert about Routh to the State Department. A State Department spokesman did not respond to a request for comment.

Evelyn Aschenbrenner, an American who served in the administration of the Ukrainian International Legion until June, told Routh by text message late last year to stop his “absurd” efforts to recruit Afghan soldiers to fight in Ukraine. “You are absolutely not helping anything by doing this,” Aschenbrenner wrote. “Please. Do less.”

For Aschenbrenner, the news that Routh was arrested in connection with a possible assassination attempt did not come as a surprise. “There’s a streak of zealotry in him,” she said. “I knew he was not firing with all pistons.”

Back in Hawaii, however, Routh’s appearance in the news — and the sight of at least a dozen agents combing through his home early Tuesday — was met with shock.

Strader, Routh’s neighbor, said Routh was “kind of in his head” but he never imagined him to be capable of violence. Routh never spoke with Strader about Ukraine or Trump, he said. Earlier this year, Routh and his partner posted Biden-Harris campaign signs along the busy highway in front of their house, said Strader, 36, a solar engineer. A beat-up truck parked outside the home bore stickers for Biden-Harris and Camp Box Honolulu, Routh’s company.

Bill Braden, a painter in Hawaii, has known Routh for about five years, ever since Routh sold him a trailer that Braden uses for guests. Braden’s daughter also bought a unit from Routh. Routh and his partner are “hardworking, down-to-earth people,” Braden said. “I thought he was a good guy.”

Levi, the vanilla farmer, had a similar view — at least initially.

Routh was older but “pretty cool,” Levi said, and enthusiastic about his work.

But the mobile shop Routh built for Levi had crooked shelving and an improperly installed bracket. After contacting Routh and receiving his angry reply, Levi decided the dispute was no longer worth his time.

“He wasn’t a threat, he just ripped me off,” said Levi, 40.

In recent months, Routh posted criticism of Trump on the social media platform X, formerly known as Twitter. Trump’s campaign slogan should be “MASA” or “Make Americans Slaves Again,” Routh wrote. He also offered to provide “thousands” of Afghan soldiers to quell unrest in Haiti.

In his book, published in 2023, Routh described himself as neither a Democrat nor a Republican. He indicated that he voted for Trump in 2016 but came to regret that choice. “I must take part of the blame for the retarded child we elected,” he wrote.

Toward the end of his account, Routh grew both morbid and grandiose. “One way or another I doubt I will make it out of this year alive,” he wrote, saying that he might be killed by the Taliban or by Russia.

On Sunday, police apprehended Routh fleeing north on Interstate 95 in Florida. He showed little emotion, the county sheriff told a local television station, and never questioned why the police were there.

Felton and Dennis reported from Greensboro, N.C., Slater from Williamstown, Mass., Hennessy-Fiske from Houston, Wax-Thibodeaux from Washington and Stern from Kyiv, Ukraine. Mark Berman, Nick Miroff, Aaron Schaffer, Samuel Oakford and Drew Harwell contributed from Washington and Tom Hays from Kaaawa, Hawaii.