This article was published in partnership with The Marshall Project, a nonprofit news organization covering the U.S. criminal justice system. Sign up for their newsletter, or follow The Marshall Project on Facebook or Twitter.

By the time Richard Midkiff walked out of a Florida prison last year at age 42, he had spent more than half his life behind bars for a crime he committed when he was 19.

Midkiff has now restarted his life: A full-time paralegal in Ocala, Florida, and the president of the board of a national organization providing legal help to incarcerated people, he begins his busy workdays at 5 a.m. And last month, he proposed to his fiancée, Marianna Kuchma, on the beach.

But Midkiff may not have his freedom much longer. Because of a legal dispute over the wording of his 1997 plea agreement for his role in a murder — and despite the fact that he has not committed any new offenses — a Florida court on July 2 ordered him to report back to the Department of Corrections to spend 15 more years in prison. He was given 15 days to challenge the decision.

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In its ruling, the 5th District Court of Appeal noted that Midkiff was a legal adult at the time of his crime, not a juvenile deserving of more lenient treatment. At the same time, the court acknowledged in a footnote that Midkiff appeared to have completed his prison time in a “remarkably favorable way” and to be a model of rehabilitation.

His former warden agrees. Midkiff is the “very embodiment of how we would all ideally want the justice system to transform people into productive, loving citizens,” said Kim Southerland, who ran Marion Correctional Institution when Midkiff was serving much of his sentence there.

A warrant could be issued to take Midkiff back into custody as early as this week, though he is seeking a stay while he pursues an appeal. With the clock ticking, he is scrambling to get his fiancée’s engagement ring resized and to pay his elderly mother’s bills — he worries that he may never see her again as a free man.

And along with grappling with the possibility of “going right back to a place where I was told what I can eat, when I can shower, how I can interact with my family,” Midkiff said, he knows a new danger awaits him in prison: “I haven’t even gotten around to contemplating how I’m headed into a COVID-19 breeding ground.”

A transformation behind bars

In 1996, when Midkiff was 19, he and a 17-year-old acquaintance robbed a man in the Orlando area who they thought would have drugs. Midkiff sat in the getaway car while his friend, J. Patrick Swett, went inside the home with a gun. “This doesn’t take away either of our guilt, which I have been trying to reckon with ever since, but nowhere in the realm of possibility did I think he would shoot this person,” Midkiff said.

Both Midkiff and Swett were charged with first-degree murder; under the legal doctrine of “felony murder,” anyone involved in a crime that turns into a homicide can be charged with the killing even if they didn’t pull the trigger. Midkiff agreed to plead guilty to second-degree murder and spend 38 years in prison.

Richard Midkiff when he was 16.Courtesy of Richard Midkiff

The victim’s family, according to court records, wanted the shooter to get a longer sentence than Midkiff, so the judge gave Swett 38 and a half years. (Neither the victim’s family nor Swett, who was also released from prison, could be reached for comment.)

In prison, Midkiff by all accounts transformed himself. He started a program called Story Time Dads, which helped incarcerated fathers record videos of themselves reading books so that their children at home could read along with them. He was also the creator and program coordinator of a prison school called SAGE, which provided dozens of classes on topics including public speaking, interviewing, financial literacy, real estate, creative writing and philosophy.

“I even started going to him for help — I’d ask him, Can you build a new program for me to meet this need, or can you work with these inmates?” said Southerland, the former warden.

Midkiff also became a certified law clerk and one of the most prolific “jailhouse lawyers” in Florida, according to his advocates across the state.

Richard Midkiff inside the Marion Correctional Facility.Courtesy of Richard Midkiff

So he took note when the U.S. Supreme Court issued a series of rulings in the 2010s declaring that prisoners who were sentenced to decades behind bars as juveniles — meaning under 18 — deserve to have their sentences reviewed to see if they had grown out of the adolescent mindset that contributed to their crime.

Midkiff’s co-defendant, Swett, who was 17 at the time of the crime, sought such a review and was granted a new sentence: time served. He was freed in 2018.

With the help of an outside attorney, Midkiff immediately filed a motion saying that the original plea agreement, as requested by the victim’s family and verbally agreed upon by all parties, said that the shooter should get more prison time than the getaway driver. Therefore, if Swett’s sentence was being shortened, so should his. (The victim’s family did not attend Midkiff’s hearing to fight his release.)

A judge agreed with Midkiff’s argument, and he was released in June 2019.

‘I have bad news’

Going free after more than two decades “was kind of like being a newborn except knowing how to walk and how to speak,” Midkiff said. Once, when he was waiting to cross a street, he jumped when he heard a robotic voice coming from the traffic light say, “Don’t walk!” His first night sleeping in a friend’s house, in a room with a soft bed and a door that he could open himself, he nearly had a panic attack.

On Midkiff’s first Friday out, he went to dinner with Kuchma, who had been writing to him for years after being introduced to him by her mother, who was a prison volunteer. (The day she had planned to come see him in prison for the first time happened to be the day after he was released; he had to call her to tell her that he was free and to cancel the visit.) They’ve been together ever since.

Richard Midkiff proposed to Marianna Kuchma on the beach last month in Florida.Courtesy of Richard Midkiff

They both knew that the Florida attorney general’s office had filed an appeal opposing Midkiff’s release, but they were not concerned. The trial court judge had ruled strongly in Midkiff’s favor, and he had strong evidence of his rehabilitation — support from prison staff and volunteers, as well as colleagues on the outside.

Since his release, Midkiff has worked on hundreds of legal cases, with a special interest in those involving juveniles. He’s also still in touch with his former warden, who asks him “about ideas for how to help these guys,” Southerland said. “Which he doesn’t have to do. He could just move on with his life and forget prison.”

In February, Midkiff flew to New York City to speak to law students at New York University about his jailhouse lawyer work.

“He was so generous with his knowledge,” said Sukti Dhital, executive director of the NYU School of Law’s Robert and Helen Bernstein Institute for Human Rights, who invited Midkiff. “This story is not just about him but about all those he’s served and continues to serve.”

Through NYU, Midkiff became board president of the Legal Empowerment and Advocacy Hub, which works to democratize the law by helping incarcerated people and pre-trial defendants themselves use it.

Apart from his work, Midkiff has spent the past year enjoying nonprison food and convincing Kuchma’s mother and siblings to let him marry her.

But then, after a year of freedom and just weeks after getting engaged, Midkiff’s lawyer called him. “I have bad news,” Mark O’Mara said simply. (O’Mara, an Orlando-based criminal defense attorney, is best known for representing George Zimmerman, including in a libel case against NBCUniversal, which owns NBC News; the suit was later dismissed.)

The appeals court had found that the language saying that Swett should get more prison time than Midkiff was written in Swett’s plea deal, not Midkiff’s. Therefore, Midkiff had no legal grounds to benefit from it.

Midkiff had long believed in the legal system — and he had trained himself while incarcerated not to cry. But the tears came quickly.

It all rushed back: “The 23 years of smells, of sounds, of fears, frustrations, regrets and the great losses of being in prison,” he said.

Undergirding the court’s ruling is the idea that Midkiff, who was a year into being a legal adult at the time of the crime, should not be able to benefit from Supreme Court rulings that said juveniles sent to prison for decades should get a second chance.

“Juvenile resentencing is not newly discovered evidence” in an adult’s case, the appeals court ruled.

But many experts on crimes committed by teenagers question the basis of the hard line that the court system draws at age 18. Brain science shows that there is no or very little difference between a 17-year-old and a 19-year-old in terms of impulse control, risk taking, being easily influenced by peer pressure and considering the consequences of one’s actions.

“There is no magic birthday when someone transitions from a child to an adult,” said Lael E.H. Chester, director of the Emerging Adult Justice Project at the Columbia University Justice Lab, which focuses on 18- to 25-year-olds.

Midkiff’s case captures many aspects of what’s wrong with the American system of punishing young people, youth advocates said. For instance, the notion that everyone involved in a crime, even the driver, should be charged equally: This especially affects teens, who tend to be influenced to do more impulsive, negative things when they’re in groups, research shows. And then there’s the notion of thinking of sentences as a strict number of years to be enforced no matter what, ignoring any rehabilitation that has occurred.

Pleas for freedom

Midkiff and his legal team are pursuing a few strategies to keep him out of prison in a state where COVID-19 cases are spiking and 175 percent more common behind bars. But they are running short on time.

The first option would be to get Gov. Ron DeSantis, a Republican, and the state clemency board to commute his sentence. Midkiff had filed a petition for clemency while he was in prison, but once he got out, he assumed it was no longer necessary and let the application lapse; his lawyers are trying to update it and get it back on the governor’s desk.

Kuchma’s family members have all written to DeSantis pleading with him to help “Richie,” as they call their soon-to-be in-law. “Our family has embraced him and have a deep respect for who he is today,” her mother wrote. “The grandchildren look up to him! I have never seen my daughter so happy.”

Richard Midkiff and his fiancée, Marianna.Courtesy of Richard Midkiff

DeSantis’ office did not immediately respond to a request for comment.

A spokeswoman for the state attorney general’s office, which argued in a brief that Midkiff’s original plea deal did not entitle him to a shorter sentence, said in an emailed statement that nothing precludes him from seeking clemency “considering the unique circumstances of his case.” She declined to comment further because the case is ongoing.

The other possible route to continuing Midkiff’s freedom is through the courts. A three-judge panel of the appeals court decided that he should return to prison; now he will try convincing either the full court or the Florida Supreme Court, or even a federal court, to take up the case.

If he gets a hearing, Midkiff’s legal team said that he would make an argument based on the common-law concept of “manifest injustice”: the idea that a ruling that might be internally logical should still be overturned if the resulting unfairness is so clear and directly observable it is shocking to the conscience.

“I am already free,” Midkiff said. “But now it feels like any minute the cops could show up and take me back.”

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