In September 2015, Oregon’s Psychiatric Security Review Board faced a decision with potentially momentous consequences for public safety. Sitting before them in a small hearing room at the state hospital was Charles Longjaw, a 50-year-old killer and rapist judged to be guilty except for insanity.

A state psychologist warned that Longjaw was likely to resume his abuse of alcohol and drugs if the board released him from strict supervision. Once drunk or high, he would be unable to restrain impulses that had previously led to a brutal murder, an attempted murder and a vicious rape. He would attack again if “he feels disrespected or threatened in some fashion,” she wrote. “The victim could be a stranger or a friend.”

For reasons that have much to do with the limits of Oregon law, the three board members present that day decided to release Longjaw, regardless of the danger. Under the relevant state statute, the board concluded, he could no longer be classified as criminally insane.

“You are discharged,” the chairwoman said.

“Thank you,” Longjaw replied at the end of a nearly two-hour hearing in which he had not testified.

A little more than a year later, Longjaw was in handcuffs facing new murder charges.

About 6 p.m. on a November night in 2016, he repeatedly plunged a knife into the stomach and arm of a homeless man as they argued on a downtown Portland sidewalk. He walked away after the attack, leaving the man mortally wounded.

Longjaw is not the only person judged criminally insane in Oregon who was charged with violent crimes shortly after being released from state control.

Two weeks after he was arrested, the state board met again to consider the release of another man doctors had determined to be a danger to the public — Anthony W. Montwheeler. And just as in the Longjaw case, the Psychiatric Security Review Board ruled it had no grounds to hold Montwheeler under state law. After 19 years of overseeing Montwheeler’s treatment and movements, the board ruled he was free to go on Dec. 7, 2016.

Four weeks later, Montwheeler killed two people and severely injured a third near the Oregon farming town of Vale, prosecutors have charged.

Longjaw and Montwheeler were free because the state board itself is handcuffed by laws that haven’t been modified despite such high-profile cases.

Like most states, Oregon does not imprison people who commit crimes while in a diminished mental state. A court can send someone for mental health treatment rather than prison if he or she could not understand or follow the law because of a mental illness.

Over time, Oregon lawmakers and judges have narrowed the conditions covered by a plea of “guilty except for insanity,” eliminating defendants who only suffer from personality disorders and psychosis caused by substance use. Legislators intended to make it more difficult to escape criminal prosecution.

As a result, some people previously judged legally insane suddenly were eligible for release.

Longjaw was one such case. Doctors had said his mental illness arose from his abuse of alcohol and drugs, a condition that no longer qualified for an insanity plea.

Board officials said that under Oregon law they had no duty to warn the public of Longjaw’s release and no authority to monitor him once he was sent into the community. In interviews, an agency official said no one tracks the conduct of people like Longjaw once they are released from supervision.

The Malheur Enterprise has reported deeply on Montwheeler, who is awaiting trial and has said he intends to rely on the insanity defense again. The Oregon newspaper, based in Vale, has partnered with ProPublica to take a close look at this system. Together, the Enterprise and ProPublica are investigating how often someone found criminally insane leaves state supervision and returns to crime, why the state released people in the face of repeated warnings they were dangerous, and what changes might better protect the public without sacrificing the rights of those with mental illness or disabilities. The reporting team is reviewing the records of more than 600 people that the Psychiatric Security Review Board has placed in community programs or set free over the last 10 years.

Board members, appointed by the governor, declined multiple interview requests. Chairwoman Elena Balduzzi, a Portland psychologist who treats sex offenders, said in February that it was not the job of board members to speak to the public. She is the only current member who was involved in the 2015 decision to release Longjaw.

But in response to written questions, the board said it is “always on the lookout for ways to improve the system.” Asked to identify internal reviews or changes as a result of the Longjaw case, the board provided none.

“Bad — and sometimes serious — outcomes occur in many arenas, even when everything is done appropriately under applicable law and other guidelines,” the board wrote.

Sid Moore, who has been with the agency a little over two years and was named interim executive director in January, emphasized in several conversations with the Enterprise that the board’s duty is to manage the custody of people found guilty except for insanity and not create laws or regulations.

“There isn’t anything for us to do,” Moore said. “This is the law as it sits. Our job is to follow it and that’s what we do.”

The Enterprise reviewed nearly 1,700 pages of reports about Longjaw obtained through state public-records law, primarily materials the board used to decide his case. Among the documents were state hospital evaluations, police reports and court records. The Enterprise also interviewed people who have known Longjaw since childhood and state officials tasked with monitoring him. Longjaw’s latest attorney, Joe Calhoun, did not reply to multiple interview requests, nor did Longjaw’s previous lawyers.

Longjaw didn’t respond to a letter, but transcripts of police interviews, summaries of psychological reports and hundreds of personal letters he sent from prison provide some insight into how he viewed his own actions.

In the Longjaw case, Oregon’s approach to mental illness and crime repeatedly failed to protect the public. The question is: Why?

A Rough Childhood

Loss, abuse and addiction scarred Longjaw’s early life in rural Montana.

He had lost both parents by age 7. His mother abandoned the family on the Northern Cheyenne Indian Reservation and his father died months later of a stroke in a hay field.

“I cryed so hard cause I knew I would never see him again,” Longjaw, a member of that tribe, wrote as an adult.

In the years that followed, he shuffled between group homes and foster families. Often, he lived with his grandparents, who “were so loving,” Longjaw remembered. “They never shouted at me or beat me up.”

Other relatives and caretakers abused him, he said. One foster parent sexually molested him.

By age 10, Longjaw was drinking and huffing, eventually using other drugs. He later told an Oregon psychologist that his goal was to hallucinate, black out or “get rid of himself.” He said he once tried to kill himself with a .22-caliber gun, but the safety was on. He was hospitalized at 12 and 13, and sent to addiction treatment four times. He participated in Cheyenne healing ceremonies. A month was the longest Longjaw stayed sober.

He was on the football, basketball and wrestling teams before dropping out of high school at age 17, having completed 9th grade. Tested later, he had the academic skills of a fifth grader.

At 18, Longjaw became convinced that a satanic cult was living on the reservation and wanted to kill him. He fled, pursued by what he thought were devil worshippers who had transformed themselves into ravens. Doctors later called his visions delusional. Longjaw traveled the western U.S., homeless and high, hopping off a freight car in Oregon.

His First Attacks

Longjaw made camp beneath the I-5 overpass near downtown Portland, where many homeless men lived in the dusty shadows on the edge of the Willamette River.

One winter night in 1986, Longjaw woke a stranger to ask for food. William Storey cursed Longjaw’s race and demanded he leave.

He walked away, stewing, and wondered how long it would take the man to fall back asleep. When Longjaw returned, Storey was snoring.

He crept up on Storey, grabbed a large rock and threw it down on his face. The stone split in two. He picked up one of the pieces and bashed Storey’s head again. He returned the next two nights to smash the injured man’s skull six more times. By the third night, Storey was dead.

“Kill him. Kill him. Kill him. Don’t let him live. Just kill him,” Longjaw later told police he was thinking. “See, when I’m drunk, I start feeling sorry for myself, self pity, and (I) took it out on him.”

He dug through Storey’s pockets, taking $15.20, and threw the bloody rocks into the nearby river. Longjaw stripped the man’s body, piled his clothes into a shopping cart and crossed the Burnside Bridge into Old Town, where he burned them.

On the fourth day, he returned to burn the body, but police were there.

Longjaw headed across the river to a west side neighborhood of abandoned warehouses where railroad tracks cut beneath the Broadway Bridge. He began camping near Ernest Glasby, a homeless man who was about 50 years old.

Two weeks later, Longjaw couldn’t find his Thunderbird, a citrus wine fortified with brandy that often sold for a dollar or two a bottle. He discovered Glasby drinking it.

He heard the voice of “the beast” tell him what to do — “Get rid of him. Don’t let him do that to you.”

The two fought. Longjaw gripped an industrial battery with both hands and beat Glasby. He then whipped him with a wooden stake until he was unconscious.

Glasby survived, although he spent weeks in the hospital before he could talk.

The night of the attack, police heard yelling and followed the noise to a boxcar. There, they found Longjaw sitting on packing crates while inhaling fumes from a bleach container. Shards of wine bottles scattered the floor. Black battery acid coated his hands. Blood splattered his face.

His responses to Portland police that early morning matched stories he would tell in later years after other assaults. He denied any guilt and insisted there was a conspiracy against him. Then, he switched his story, saying he had blacked out and couldn’t remember what had happened. Finally, he admitted to the crimes, saying he heard voices telling him to do it. In the end, Longjaw described the killing and brutal assault in graphic detail.

“You can probably lock me up or whatever you want to do, just get it over with,” Longjaw said. “Put me in the electric chair, whatever you’re gonna do, man.”

Insane, or Not?

Given his detailed confession, a central question loomed in Longjaw’s murder case. At the time of the attacks, was he able to understand the law and obey it?

If, by legal definition, he had been impaired by a “mental disease or defect,” Oregon law allowed Longjaw to plead “guilty except for insanity” and undergo treatment. Otherwise, he faced at least 10 years in prison and up to life.

To assess whether a defendant can plead insanity, judges rely on medical experts. Because many people who use alcohol or drugs also have mental illnesses, it can be difficult to evaluate a defendant’s state of mind at the moment of a crime.

The experts who testified before Judge William Snouffer of the Multnomah County Circuit Court disagreed about his mental state.

Two mental health professionals hired by Longjaw’s public defender concluded he was insane. One said he had drug-induced psychosis or schizophrenia. Another said his brain might be permanently damaged by drug use.

“It would take more than a prison sentence to change this individual to function in society,” wrote Robert A. Ryan, a psychologist and Cheyenne River Sioux tribal member. He suggested Longjaw could be stabilized with medicine and intensive treatment.

A psychiatrist hired by the prosecutor said Longjaw could tell right from wrong and was capable of obeying the law.

“This man is somewhat impaired but I do not think that the level of impairment reaches the point of compromising his criminal responsibility in any way,” Dr. Edward Colbach wrote.

Snouffer sided with the defense and ruled that Longjaw was criminally insane. He put the admitted killer under the supervision of the Psychiatric Security Review Board and sent him to the state mental hospital.

Because the maximum sentence for the crime was life in prison, the judge gave the board authority to supervise Longjaw until his death.

Treatment Instead of Prison

The “insanity defense” emerged in western legal theory centuries ago.

The idea is that it is unfair to punish someone who could not understand what he did was wrong because of a mental disorder, or if it crippled his ability to act appropriately. In American and British law, the insanity defense allows courts to detain dangerous people and divert them into treatment. Research has repeatedly found that people with mental illness are more likely to be victims of violent crimes than to commit them.

Oregon’s emphasis on reintegrating criminally insane defendants sets it apart from most states. Few places allow patients to step down from psychiatric hospitals into community programs. Sometimes they hold jobs and live independently with supervision.

Most of the roughly 500 people put under jurisdiction of the Psychiatric Security Review Board have been accused of serious crimes and about one-third live at the state hospital. The rest are in local programs whose professionals ask the board to gradually roll back supervision and grant people more freedom as they progress through treatment.

Moore, the board’s director, said Oregon’s approach provides a smoother transition than releasing people without services after years of round-the-clock monitoring at a hospital.

“That’s the safest patient: Someone who is stable and engaged in his or her recovery,” he said.

Moore said the board’s statistics show the strategy works. Over six years, the board reported that just 1 in 200 people committed new crimes while under the state’s supervision.

When that happens, the board said the results sometimes can be “horrible.”

“The board is always cognizant of these possibilities when considering whether it thinks the patient can be maintained safely in the community,” the board wrote in its answer to the Enterprise’s questions.

Longjaw followed all the rules — until he didn’t.

Throughout his life, records indicate he thrived under strict monitoring, earning the praise of his treatment teams. But he exploited opportunities for freedom, returning to drug abuse and then violence with no warning.

Staff at Oregon’s state hospital had not recognized that pattern when they first said Longjaw could leave with “minimal risk to others.”

The Psychiatric Security Review Board released Longjaw into the community in 1992 under the condition that he be supervised, continue treatment and not use alcohol or drugs. In Portland, he excelled in therapy, joined a Native American drum group, and completed training that led to jobs at a grocery store, a Pizza Hut and a local detox center.

Over a weekend in August 1994, he went from a model patient to a public threat.

Drunk and high again, he argued with his girlfriend, grabbing her throat with both hands. He said he had a gun and threatened to kill them both. He wondered aloud “what it would be like to kill a lot of people.”

The Psychiatric Security Review Board revoked his release, and police returned him to the hospital. He quickly settled back into a routine of compliance. Within a few months, Longjaw’s treatment team again recommended him for community care, but under “tight monitoring.”

It took the board years to find a program that would accept Longjaw. Three said they wouldn’t take him as a patient because of the risk he posed or because he didn’t fit their treatment profile.

Colbach, the private psychiatrist who had told the Portland court to imprison him a decade earlier in the murder case, weighed in a second time.

“He is somewhat glib and feels that he has certainly conquered his problems,” Colbach wrote. “I view this man’s situation with a lot of apprehension. He apparently can fall apart quite quickly and very dramatically. ... I don’t see any way that we can prevent this from happening.”

A work release program in Hillsboro, a suburb of Portland, disagreed and said that it could safely manage Longjaw. The program was designed to help people coming out of prison.

As the board prepared to release him again in 1998, a local prosecutor urged the board to reconsider, or at least impose much stricter supervision. The board did neither.

“The new proposed release plan is no different than that implemented in 1992,” wrote Russ Ratto, senior deputy attorney for Multnomah County. “Once again the community will be put at risk.”

Still, the board said Longjaw could go.

Another Attack

Five months after joining the Hillsboro program, Longjaw left one day and didn’t return.

His supervisor and the board’s director scrambled to find him, fearing the worst would happen.

In fact, he was in nearby Vancouver, Washington, at the home of a woman he had chatted with at Oregon powwows over the years. Longjaw showed up at her work, saying he had taken a short break from rehab to “clear” his head. She offered to help him find a place to stay and brought him home to talk it through.

As she boiled water for tea in the kitchen, the woman did not realize the danger she was in.

She later described how Longjaw came up behind her, rubbed against her, kissed her neck and said he loved her. She laughed, teasing that he didn’t really.

Longjaw flashed to anger.

“I didn’t come all this way for nothing,” he said.

He lifted her off the floor and carried her into another room. He raped her as she screamed for him to stop. He punched her face four times, fracturing her jaw and leaving a deep cut above her left eye. She spit two front teeth into her palm.

Threatening to kill her, Longjaw ordered the injured woman into her maroon Dodge minivan and started driving. He later said he thought about choking her to death. When he slowed near a stop sign, the woman jumped out of the car and bounced along the ground before getting up and running to a friend’s house to call police.

Cops arrested Longjaw within an hour and his interview with investigators followed the by-now familiar script. At first, he said it had been a consensual encounter. He said he didn’t recall everything that he did and then that he lost control and that it was “the beast Satan within telling him to do this.” He later said cops had framed him, a plot revealed to him by God.

Longjaw admitted raping the woman, saying years later that he did so because he “didn’t want to come back to the state hospital.” He figured his community release was going to be revoked for missing curfew. He preferred prison to the hospital.

His public defenders recommended that he present an insanity defense or tell the jury about his time in a psychiatric hospital. Instead, Longjaw fired his lawyers and asked the judge for permission to represent himself.

He got his wish and was convicted of rape, assault and kidnapping. He was sentenced in October 1999 to serve 18 years in a Washington prison, almost twice as long as the standard penalty.

The Oregon board responsible for keeping the public safe from Longjaw acknowledged no fault in “the very unfortunate incident.” Its executive director told a local newspaper that it had done “everything” possible to protect the public.

Back at the Hospital

As the years ticked by on Longjaw’s Washington prison sentence, courts in Oregon made a critical clarification to the state’s definition of criminal insanity that would open the way to his freedom. In 2005, the Oregon Supreme Court ruled that “substance dependency” by itself was not a basis for the insanity defense. The justices said lawmakers didn’t intend for it to apply when the perpetrator only suffered from dependence on drugs or alcohol. (In 2018, a Court of Appeals case further found that “transitory, episodic, drug-induced psychosis” also did not qualify for the defense.)

That diagnosis had been a key part of how the Psychiatric Security Review Board gained custody of Longjaw after the 1986 murder.

When Longjaw was released from Washington prison in the summer of 2015 — 16 years after the Vancouver rape — he was brought back to the state hospital in Oregon. But almost immediately, doctors there questioned whether the board could hold Longjaw. Because of the Oregon Supreme Court decision, a diagnosis of substance dependence alone did not qualify for an insanity defense. Doctors in Oregon reviewed Longjaw’s long history of medical records and made new observations. The board found that Longjaw’s diagnoses were now all related to substance abuse and dependency, or Antisocial Personality Disorder, which also did not qualify for the defense.

Under Oregon law, board members could have kept him under supervision if they found he had a mental disability. The earliest evaluations of Longjaw had noted brain damage from drug use. But a state neuropsychologist said in 2015 that his impairment was not disabling.

He must be released, the doctors told the board.

A major shift in diagnosis is not unheard of, the board said recently in its answers to the Enterprise’s questions.

“Mental health issues are multi-faceted and as such it is difficult for everyone involved to make an exact diagnosis,” they wrote.

As was by then routine when a treatment team recommends a patient for release, another hospital mental health professional analyzed the likelihood Longjaw would commit new crimes.

If Longjaw acted like other men “with the same risk profile,” clinical psychologist Pamela Buchanan wrote, there was an almost one-in-three chance he would attack someone within five years. Sex crimes were likely “early and often.” She also highlighted his history of escaping from custody.

“Much of his offending has been impulsive, opportunistic, and a way of exerting some sense of control over the person or situation,” she wrote. “It takes little to motivate his engagement in violent criminal acts.”

Before the Board

That warning was in the stack of 181 exhibits before the Psychiatric Security Review Board as it met in September 2015 to consider Longjaw’s fate.

The pages traced his quick fall into violence each time he had a chance to use drugs. They detailed his dayslong murder of Storey, the brutal attempted murder of Glasby, the threats to kill his girlfriend, and the vicious rape of a woman who had wanted to help him.

But danger alone wasn’t enough to hold Longjaw.

The board defended the strict standard.

“If the law allowed for the Board to maintain under its jurisdiction those who are dangerous but who do not have a qualifying mental disorder, the potential would exist that it could find itself in a position to maintain jurisdiction over anyone who was considered dangerous, even if they didn’t have a mental illness,” the board wrote in response to questions. “Criminal insanity under the law requires both, and removing part of the law could lead to violations of the rights of some in the community.”

State law requires board members to answer two questions at every hearing: Does the patient have a qualifying mental disorder? And does that mental disorder make him dangerous? Answering “no” to either question leaves the board no choice but to release him from supervision.

The hospital doctors answered “no” to the crucial first question.

“The most you can say is, he is vulnerable to a substance-induced psychosis, but there doesn’t seem to be an independent illness,” said Dr. Simrat Sethi, a forensic psychiatrist.

Assistant Attorney General Lynn Larsen insisted Longjaw actually had an undiagnosed mental disorder and should therefore remain in the hospital. If released, he said Longjaw was likely to attack again.

In a last-ditch move, Larsen offered his own diagnosis. He pointed to hundreds of handwritten letters Longjaw sent from prison to his ex-girlfriend’s elderly mother. In them, he praised the woman’s “sexy” voice, saying he wanted to marry her and have children. He said he was “a real man” who would keep her happy, remembering one time when she wore “red, tight pants.”

Larsen said the letters showed Longjaw was delusional.

Ratto, the Multnomah County prosecutor, agreed the board should keep Longjaw in custody. He cited the letters and reports of depression or attempted suicide throughout Longjaw’s record.

“This man does have a mental disease or defect,” Ratto said.

Longjaw’s defense attorney, Harris Matarazzo, said the lawyers’ personal views were irrelevant.

“They have not brought an expert in. The fact that they may feel it’s a mental illness, that’s great, but that doesn’t carry any weight here,” said Matarazzo.

The three members of the board present that day —Jenna Morrison, a community supervision officer; Balduzzi, the psychologist; and then-chairwoman Katie Lieber, an attorney — stepped into an adjacent room to deliberate privately.

They concluded that Longjaw lacked a qualifying condition but was dangerous. Lieber said the decision was influenced by the Oregon Supreme Court ruling a decade earlier. At one point, she stumbled, noting that board members “unfortunately” had no other options.

“You no longer qualify for jurisdiction under this board and you are discharged,” she said.

The board and state hospital released Longjaw with no housing support, no community services and no monitoring. Officials say they don’t have authority to do anything more once someone is released.

Longjaw left the state hospital. Because of his rape conviction, he had to check in weekly with a Washington probation officer and submit to monthly drug tests.

Otherwise, he was a free man.

“I’ve never been free without a leash,” Longjaw told a psychologist before his hearing.

Another Conviction

Thirty years after his first murder, Longjaw was back on the streets of Portland.

As doctors predicted, he began using drugs again after his release. Again, he roamed the city homeless and high.

A few days after that, Longjaw stood outside the downtown Embassy Suites as he argued with Mark Whelan, another homeless man.

Longjaw pulled a Bear Grylls knife from a bag and stabbed Whelan twice in the gut and twice in the arm. He then folded the knife, put it in his coat pocket, removed his jacket and stuffed it in the bag held by a third man.

Whelan stumbled down the sidewalk and collapsed, dying days later in a local hospital. Longjaw was soon back in custody, charged again with murder.

“This was an incredibly dangerous individual who should not have been out on the streets,” said Multnomah Deputy District Attorney Melissa Marrero, in an interview about Longjaw’s latest murder. “You ask yourself 20 different ways what could have prevented this. When there’s a change in law that changes the expectation of what would happen with that person, it’s a tough question to answer.”

Jurors convicted Longjaw in March. He was sentenced to life in prison but is eligible for parole in 2043 when he will be 75 years old.

His earlier insanity plea meant he hadn’t been found criminally liable for the 1986 attacks, so he avoided an aggravated murder charge that would have opened up the possibility for him to be sentenced to life without parole or to be given a death sentence.

The adoptive mother of Whelan, Longjaw’s victim, was torn by the conviction. Susan Fey, a Colorado psychotherapist, understands how people with mental illness can be demonized even when they are not violent. Whelan himself had mental health issues that likely stemmed from an abusive childhood.

“Mental illness is scary to people. They’re afraid of it. They’re afraid of the people that have it. And they certainly look down upon them as something less than what we call normal,” she said. “We have a lot more to learn about human beings and how to heal them.”

Fey said a system focused on restorative justice, like those in some European countries, could have helped Longjaw long before he committed his first violent crime. In that model, offenders, victims and community members agree to focus on rehabilitation and skills training, rather than on punishment.

She said the Psychiatric Security Review Board and Oregon leaders must learn from Whelan’s death to make changes that could save lives. She said Oregon’s exclusion of some diagnoses from the insanity defense is “very questionable.”

The board said changes to the law in the last 30 years, such as excluding people with some disorders from using an insanity defense, were designed “to minimize the danger to the public.”

Moore, the board’s director, said he saw no flaw in how the board handled Longjaw’s case, saying mishaps are inevitable even in the best systems.

“There just isn’t any preventing things,” he said.