(JACKSON, Mo.) — The nightmare gripping Ken Middleton’s family appeared to be possibly over in 2005.

The same judge who in 1991 sentenced the Kansas City, Missouri, man to life without parole plus 200 years for the shooting death of his wife, ruled to vacate that same ruling and ordered that he receive a new trial based on a series of irregularities that the judge concluded made his original trial unconstitutional.

However, Middleton was never granted a new trial despite that overturned conviction nearly 20 years ago.

The reason is a technicality in Missouri state law that gave jurisdiction in the case to the Missouri Court of Appeals, not with the Jackson County circuit court. Despite the evidence Judge Edith Messina cited in her motion to declare his trial unconstitutional due to ineffective assistance of counsel, her ruling was overturned and ultimately proved toothless.

As a result, Middleton, 78, remains behind bars. He maintains his innocence and said his wife shot herself by accident while he was sleeping.

According to the decision obtained by ABC News, his lawyer failed to present evidence to the jury that no blood was found on his shirt, gun residue evidence went missing, there were irregularities involving the handling of the body at the crime scene, and, among other things, Middleton’s original attorney failed to perform basic duties like interviewing witnesses and calling independent experts. In fact, he presented no evidence at all, the ruling said.

“It upsets me so much,” Cliff Middleton, Ken Middleton’s only child who has dedicated his life to making sure his father does not die in prison, told ABC News. “The justice system in Jackson County is broken.”

The saga is now in its 32nd year, but the family said a state law passed in 2021 gives them renewed hope. It bypasses the appeals court by empowering local prosecutors to file a motion that asks the court to vacate or set aside a guilty verdict based on new information that shows the convicted person is not guilty.

The new law is already responsible for the release of several men in Missouri, including Kevin Strickland, who spent four decades in prison in a triple murder case, and Lamar Johnson, who walked out of prison a free man after serving 28 years for a murder. The reversals of more cases are expected over the coming year, experts told ABC News.

Now all the family must do is to get the Jackson County District Attorney Jean Peters Baker to appeal for Middleton’s release based on all the constitutional violations Messina cited nearly two decades ago.

But she said she will not.

Baker will not re-open the Middleton case because, unlike Messina in 2005, she does not believe the new evidence presented at that time reflects a wrongful conviction, according to spokesperson Michael Mansur.

“Our office greatly admires [Messina] and knows she has a reputation as a fair judge. But we don’t agree with her on this particular ruling in this case,” Mansur told ABC News.

What constitutes ‘new’ evidence

In a 2019 memo provided to ABC News by Mansur, Baker’s office challenges Middleton’s claims of new evidence primarily because of a procedural reason: The failure to introduce it at his original trial was “the result of counsel’s incompetence,” even though, according to Baker, it was available at the time. Robert Duncan, Middleton’s original attorney, died of a heart attack in 1996.

“By this definition of new evidence, Middleton does not have any new evidence. All of his witnesses either were available at the time of trial or — in the case of experts — could have been available at the time of trial if Mr. Duncan had sought out such experts,” Mansur writes. In addition to arguing ineffective assistance of counsel, Middleton has claimed the missing gun residue evidence from the victim’s left hand suggests police tampering, Baker’s office said it is unclear if it was collected at the scene, but even if it was, “it would not be conclusive” that the victim shot herself.

“Middleton was aware of this issue at least as early as 1993 … and could have raised his current complaints at the proper time,” the memo reads. “The weight of the evidence does not support the sinister spin” by Middleton.

The family and supporters characterize Middleton as the victim of a bureaucratic mess.

“We have unchallenged information of an erroneous conviction, yet [Baker] will not file. That’s just unbelievable to me. It’s a dereliction of duty,” Cliff Middleton said.

Jason Flom, a co-founder of the Innocence Project, a legal non-profit involved in criminal justice issues, told ABC News in a statement that Middleton’s case “is one of the most insane and terrifying miscarriages of justice I have ever heard of.”

Missouri’s exonerations record

Retired Missouri Supreme Court Chief Justice Michael Wolff, now a professor emeritus at the Saint Louis University School of Law, said the failure to initially grant Middleton a new trial in 2005 “was a procedural glitch.” “The new statute was intended to correct that, but the problem is, it’s a narrow pathway because it’s only at the bequest of the prosecutor” who is not obligated to pursue exoneration,” he said.

In Missouri, which remains one of 24 states that still has the death penalty, “there’s a lot of bias in favor of keeping convictions final,” Wolff said.

“This new [law] does bring some hope to people but hope is only pivotal if the prosecutor can be persuaded to pursue this,” Wolff said.

Another issue with the law is politics, said Ken Middleton’s attorney Kent Gipson. Because district attorneys are elected positions, he said putting the power in their hands is inherently “stupid.”

“A prosecutor doesn’t want to politically admit that their office put an innocent man in prison for 30 years. That couldn’t do anything for their future political career, even if it wasn’t on their watch,” he said.

According to the National Registry of Exonerations, a project jointly operated by the University of California at Irvine, Michigan State University and the University of Michigan, exonerations nationwide have been steadily rising over the last three decades: from 24 in 1989 to 268 in 2022. However, Missouri only logged a single exoneration last year and the highest yearly number of those exonerated in the state since 1989 is five — in 2010 and 2013, respectively.

Maurice Possley, a senior researcher at the registry, said the reason for such diminished numbers is cultural. “It’s a state that is not particularly open minded to the idea that people are wrongly convicted. Prosecutors tend to be more willing to dig in to preserve convictions,” he said.

Even counties with conviction integrity units, like Jackson County, are not immune to slow-walking wrongful verdict cases, Possley said.

According to Mansur, the unit helped to successfully overturn just one case in its four years of existence and currently doesn’t “have another one right now in which we’re planning to move ahead on.”

New prosecutor, judge sought

Gipson is currently asking for a special prosecutor and a new judge to address Middleton’s case. Last week the Kansas City Star editorial board blasted Baker and said she needed to reopen the case or recuse herself due to several conflicts of interest that Gipson outlines in his filing. For one, the judge who refused to hear Gipson’s motion to disqualify Baker worked under Baker in the prosecutor’s office before her current appointment.

Mansur said no conflict exists because Phillips “sits over criminal cases from our office routinely” and “was not a member of this office at the time of Middleton’s trial.”

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