Who Is Preston Shipp, The Former Prosecutor Who Went On To Support Cyntoia Brown's Release?

When ex-prosecutor Preston Shipp first recognized Cyntoia Brown while teaching a class at a local prison, it came as a "terrible realization" that the same woman who came across as a motivated, bright student was also someone he'd helped keep behind bars years ago. 

Today, Shipp serves as the senior policy counsel for The Campaign for the Fair Sentencing of Youth, an organization devoted to eliminating extreme sentences for young people and fighting for their right to a second chance. But before working as an advocate for criminal justice reform, he was an appellate prosecutor for the state of Tennessee, and Cyntoia Brown was an inmate whose appeal he had argued against. He told a judge that she should not be released from prison and that the sentence she'd received had been just, only to run into her years later in the spring of 2009 when he was teaching a class at the Tennessee Women's Prison. Brown, he realized, was actually one of his students.

Preston Shipp Photo: The Campaign for Fair Sentencing of Youth

"I was very nervous as to what kind of response I was gonna get," he recalled while speaking to Oxygen.com. "I didn't know whether she was going to cuss me out one side and down the other, drop out of the class, quit the college program. Or maybe I'd never see her again. Maybe she'd just never come back."

Brown, by then, had shown herself to be an "excellent" student, one who loved to read and be challenged, and who was "fired up" to talk about the criminal justice system.

Today, Brown is still passionate about criminal justice reform. Her story is one that gained national attention: as a 16-year-old runaway, she fell in with a pimp who forced her into prostitution. One evening in 2004, Brown was picked up by a 43-year-old real estate agent named Johnny Michael Allen, and he took her to his home. The two never had sex, but Brown would later tell authorities that she feared for her life; he showed her the many guns in his home, talked about his history as a sniper and acted strangely throughout the night, she said.

Cynthia Brown-Long poses in Nashville, Tenn. Photo: AP

While the two were lying in bed that night, Allen reached over, seemingly to retrieve something from his side of the bed, Brown told police. What happened next would change both of their lives forever: Brown feared that he was going to kill her, she said, and so she took out the gun that her pimp had given her and fatally shot him. She then took money from his wallet — not wanting to return to her pimp empty-handed, she claimed, according to CNN — and fled.

Brown would ultimately be arrested and tried as an adult. She was convicted of first-degree murder and robbery and sentenced to life in prison, with state laws making her ineligible for parole until she'd served 51 years, USA Today reports.

However, unlike so many others who are convicted of violent crimes as minors, Brown's story has a happy ending. In last few years, her case gained national attention, with celebrities like Rihanna and Kim Kardashian sharing her story on social media. She was granted a clemency hearing in May 2018, and numerous people spoke in support of her, including Shipp, who even wrote a letter to the governor on her behalf.

All those years ago, after both Shipp and Brown — teacher and student, then — realized that they had history together, they were still able to build a friendship.

"I think the way that she was willing to reconcile with me and see beyond the role that I played in her case is a testament to the generosity of her spirit," Shipp said.

Helping Brown argue for her release during her clemency hearing in 2018, nearly a full decade after teaching her in class in 2009, felt like a "fitting bookend," he recalled. The two are still friends today.

It turned out that 2019 was a monumental year for Brown. Following the much-talked about hearing, outgoing Tennessee Gov. Bill Haslam granted Brown clemency, and she was released in August 2019. She's gone on to become a powerful advocate for criminal justice reform, write a best-selling memoir, and marry Christian rapper J. Long.

But while Brown's story may seem remarkable, the uncomfortable truth is that the circumstances that landed her behind bars aren't, Shipp and other advocates say. Brown may have found justice, but there are countless others like her who aren't as lucky.

"That's what frustrates me about Cyntoia's case. Even though we care and we signed an online petition to help get the governor of Tennessee to grant her extraordinary relief in the form of executive clemency, the laws in Tennessee haven't changed," Shipp said. 

Under Tennessee law, child offenders younger than 18 have the possibility of being sentenced to life in prison, without being eligible for parole until they've served 51 years, according to the ACLU. It's the harshest minimum sentence in the nation, according to The Tennessean.

"You [can] take another 16-year-old person who commits a crime of violence, try them as an adult, and throw them away for the rest of their life because the Tennessee legislature has not abolished life without parole for kids," Shipp said. "It has not created a mechanism through which children ... would have the opportunity to have their sentences reviewed and possibly have a second chance."

One answer, he went on to say, would be to encourage those in power to "pass laws that will take into account the particular characteristics of young people, because young people can and do change."

Shipp's work is proof of that. While working as an appellate prosecutor in the Tennessee Attorney General’s office, Shipp volunteered and taught college classes at local prisons, and it was by getting to know the inmates — people like Cyntoia Brown — that the flaws in the criminal justice system became impossible to ignore. He quit being a prosecutor in 2008, a decision that was inspired in large part by his faith, and headed down a path that was more in line with his values.

Today, he works with The Campaign for the Fair Sentencing of Youth, an organization "committed to the idea that no child is born bad and every child can grow beyond the worst moment of that child's life," he told Oxygen.com. The campaign has helped more than 600 people, who were "told as children that they were gonna die in prison," regain their freedom and go on to live full lives as valuable members of their communities, Shipp said.

"When we give people an opportunity, not a guarantee — when we give people an opportunity to demonstrate that they have been transformed, they will make the most of it," Shipp said. "The recidivism rate for people who are sentenced as children and who served 10 or 15 or 20 years, the recidivism rate is through the floor." 

"So we can give them second chances. It's not a threat to public safety. It doesn't diminish our concern and compassion for victims, because we have to think about victims as well, but second chances are not some kind of an affront," he continued. "They don't diminish our compassion for victims; it recognizes that a lot of the people who commit these crimes are victims themselves, and so we need to cultivate that sense of understanding and compassion when we deal with these folks because we know that they can change. Children have the capacity to make positive change."

And the laws are changing, however slowly. Virginia's governor signed a bill earlier this year that would make inmates sentenced as minors eligible for parole in 20 years, effectively eliminating life sentences for children, according to NBC Washington. More than 20 other states have made similar moves, including Arkansas in 2017, Utah and South Dakota in 2016, and Connecticut the year before that, according to the Equal Justice Initiative.

However, despite the considerable progress that's been made in recent years, advocates say there's still work to be done. In the age of social media, some of that work gets started online. Celebrities like Kim Kardashian have been able to use their sizable social media platforms to call for, and enact, real change. Kardashian in particular, while initially known by many as a reality TV star, has become a fierce advocate for criminal justice reform, and has, with the help of lawyers, successfully fought for the release of numerous inmates, including Alice Marie Johnson, a grandmother who was handed a life sentence in 1996 for a first-time drug-related offense.

Kardashian also partnered with Oxygen on "The Justice Project," which shone further light on criminal justice issues and the problems associated with mass incarceration.

"My Life Has Changed Probably In More Ways Than I Ever Would've Imagined:" Kim Kardashian West Talks Social Justice Work

But while there are obvious advantages to mobilizing support on social media, activists need to do more, Shipp said.

"I think that the attention that some of these cases generate on social media can be helpful for starting a conversation, and for inspiring people to try to make their voice heard, but I think also there can be kind of a downside where people assume that the Cyntoia Brown case, it's the only one out there, and once we get Cyntoia taken care of, there's nothing else to do," Shipp said. "'This was one outrageous case and the system is working really well in all the other cases, this is just one where it really went wrong,' and that is not true." 

"Cyntoia's case, again, is very typical for how young people who commit crimes of violence are treated and so if we think that by signing a petition — and I think the governor granted her clemency application based on the public outcry, I don't think he would have granted it otherwise because there haven't been other grants in cases like hers — the people do need to know that hers was not some sort of an outlier and some travesty of justice," he continued. "No, the law functioned in Cyntoia's case exactly the way that it is designed to do. And so her transfer [to an adult facility] was proper, her conviction was proper, [and] her sentence was proper, under the law." 

"Which means the law needs to change."