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Death Sentences

He’s Too Mentally Ill to Execute. Why Is He Still on Death Row After 45 Years?

Raymond Riles has been on death row longer than anyone in America. He’s one of many who have languished there for decades with severe mental illnesses.

Raymond Riles, right, with Ronald O'Bryan at the Ellis Unit in Huntsville, Texas, in 1979. In that era, incarcerated people on death row could go to the exercise yard for three 90-minute periods a week.
Raymond Riles, right, with Ronald O'Bryan at the Ellis Unit in Huntsville, Texas, in 1979. In that era, incarcerated people on death row could go to the exercise yard for three 90-minute periods a week.

Raymond Riles arrived on Texas’s death row in 1976, the year President Gerald Ford lost his reelection bid and the first “Rocky” movie debuted in theaters. Riles had been sentenced to death in Houston for killing a used car salesman named John Henry.

Forty-five years and eight presidents later, Riles remains there, having survived three cancelled execution dates to become the longest serving death row prisoner in the state—and likely in the nation. He lives in near-total solitary confinement. Like many longtime death row prisoners, experts have repeatedly deemed him to be delusional and “grossly psychotic.” Sometimes he describes himself as God or “King Moto-Cherry Velt-Love.” Other times he worries that he will be sacrificed to Satan by his demonic captors. He once set himself on fire.

He may get to leave death row soon. This week, Harris County District Attorney Kim Ogg announced her support of a new punishment trial for Riles, paving the way for him to get a life sentence and live out his days in the general prison population if judges agree. “These cases are heartbreaking because the process takes so long,” Ogg said in a press release. “It just prolongs justice and healing for the families of the dead.”

Riles’s case—and the time it has taken to resolve it—is far from unique and raises troubling questions about how prisoners can languish on death row for decades, even when they are too mentally ill to execute.

In 1986, the Supreme Court ruled that states can’t execute people who don’t understand why they are being put to death and should be legally defined as “incompetent.” The decision left it up to state courts to decide who fits this category. Defense lawyers note that plenty of people have been executed despite evidence they are severely mentally ill, including Lisa Montgomery, the only woman executed by the Trump administration. But even when a state court agrees to stop an execution, the prisoner is not automatically removed from death row.

“If someone is deemed incompetent that should be the end of it, we should move them off the row,” said Amanda Marzullo, a death penalty lawyer and former director of the nonprofit legal group Texas Defender Service. “And sometimes that happens, but it’s the exception not the rule.”

Several states have at least one person like Raymond Riles. In Pennsylvania, a judge ruled in 2010 that George Banks was not competent to be executed for killing 13 people back in 1982, but he remains on death row.

South Carolina’s longest-serving death row prisoner is Fred Singleton, who was convicted in 1983 of raping and murdering Elizabeth Sease Lominack during a robbery. “He believes that he can’t be killed because he has a protective ‘genie’ that prevents the State from putting him to death,” his lawyer John Blume wrote in an email. “He also believes that he has the power to leave prison and that he often goes and visits his mother’s grave.”

Blume said he might have fought to get Singleton out of solitary confinement on death row, but decided against it. “I was worried about him being victimized in the general population due to his disability,” Blume wrote.

Legal battles over competency can last so long that the prisoner ends up dying of other causes. Lawyers for James Frazier, the oldest person on Ohio’s death row, were arguing that the 79-year old suffered from dementia and could not be executed when he died in November, likely of COVID-19.

And then there’s Riles. Both he and his co-defendant—Herbert Washington—were sentenced to die for shooting a car dealer who wouldn’t let them return a vehicle Washington had bought a few days earlier. After a court overturned their convictions in 1977, Washington took a plea deal and was released from prison in 1983. Riles went to trial and was again sentenced to death, despite his extensive psychiatric history.

His family told the court that he had always been “a little funny” and sometimes prayed in other languages or referred to himself by other names. A judge from another county attested that he’d had roughly a half-dozen members of the Riles family committed to mental health facilities over the years. That evidence, combined with repeated courtroom outbursts during Riles’s trial, was still not enough to win him an insanity plea, in part because prosecutors at the time said his psychiatric history actually made him a better candidate for the death penalty.

But after he went to death row, experts repeatedly found that he was not fit for execution. Even when he took the antipsychotic medications he was prescribed, he still harbored bizarre religious delusions.

“He does not appear to have sufficient capacity to understand the criminal justice system,” one expert wrote in a 1987 competency evaluation. Riles told the expert that he would “resurrect” and the world would recognize him as the Messiah and he would be “king of the world.”

Time and again, psychiatric examiners found that he could not be put to death under the standard set by the Supreme Court case of Florida prisoner Alvin Ford in 1986. Ford sometimes referred to himself as the Pope or ranted about Ku Klux Klan conspiracies to bury prisoners. The court ruled that it violated the Constitution to execute someone so mentally incompetent.

But the ruling didn’t demand that such people be taken off death row. Instead, so-called “Ford claims” became an issue that condemned prisoners could raise only at the last minute, after an execution date was set. If a court stopped the execution, they would not be resentenced to life; they’d just be sent back to death row in the hope that they might someday become competent for execution. Instead, they linger on death row, which in Texas and many other states means near-total isolation, exacerbating mental health problems.

"For many decades, there have been men marooned in prisons, mainly throughout the South, with death sentences that both sides know, under some sort of détente, will never be carried out,” said Joseph Perkovich, a lawyer who has represented prisoners with mental illnesses in at least five states.

The situation can be fraught for defense lawyers, who must balance the mental wellbeing of their clients against fears the prisoners will be killed if they get well. “Death row is a horrible place to be as a human being,” said Richard Burr, the lawyer who defended Ford in the 1980s. “You realize that it’s cruel to have your client living there untreated, but also cruel to have them treated and restored to competence and possibly be executed.”

At the same time, prosecutors have little incentive to push for execution dates and enter protracted fights in the courts.

“Sometimes you have tacit agreements between the parties that the best way to address this is to do nothing,” said Robert Dunham, director of the nonprofit Death Penalty Information Center. Usually, that sort of agreement isn’t something lawyers talk about publicly, but in 2018, a frustrated North Texas lawyer did, after the district attorney in Fort Worth set an execution date for a man with paranoid schizophrenia.

"He has been very psychotic to entirely, utterly out-there since about 1990," Gregory Westfall said of his client, Emanuel Kemp. "It was agreed that he was too insane to execute. But since then, the leadership [at the district attorney’s office] has changed and now they have sought an execution date.”

At the time, Tarrant County prosecutors did not acknowledge any agreement regarding Kemp’s case, and the execution was later called off for unrelated reasons. Kemp has now been on death row for more than three decades.

Similarly, Clarence Jordan, who at one point believed he was Jesus Christ, has been facing execution in Texas since 1978. Syed Rabbani, who claimed to be a foreign diplomat working for the CIA and has repeatedly sued “all life forms in all galaxies” for torturing him, has been waiting to be executed since 1988.

Clarence Jordan, facing camera at the table in the foreground, played games with other prisoners on Texas's death row in 1979.

Clarence Jordan, facing camera at the table in the foreground, played games with other prisoners on Texas's death row in 1979.

Harris County prosecutors acknowledged more than 20 years ago that Jordan and Rabbani did not qualify for execution because of their mental state.

"The U.S. Supreme Court has said you can't execute someone who is mentally incompetent, and we don't," former Harris County assistant district attorney Roe Wilson told the Austin American-Statesman in 1999. She said if three mental health experts deemed a prisoner incompetent, “we don't proceed with an execution date.”

At the time, she told the paper there were five men in that holding pattern. Decades later, three—Rabbani, Jordan and Riles—are still there.

“There’s just no real legal mechanism to reassess what should be done with those people,” said Thea Posel, who represents Riles along with fellow attorney Jim Marcus. “Our system just isn’t structured for that.”

Maurice Chammah Twitter Email is a staff writer and host of the podcast “Just Say You're Sorry,” as well as the author of “Let the Lord Sort Them: The Rise and Fall of the Death Penalty.” He writes narrative features on a range of criminal justice subjects, including the death penalty, forensics and art and music by incarcerated people.

Keri Blakinger Twitter Email is a former staff writer whose work focuses on prisons and jails. Her work has appeared in the Washington Post Magazine, the Houston Chronicle and The New York Times. She is the organization's first formerly incarcerated reporter. Her memoir, "Corrections in Ink", came out in June 2022.