For a teen’s impulsive, unthinkable act, Cyntoia Brown got an adult’s life sentence. Was justice served? 

Life Begins at Sixteen

Life Begins at Sixteen

Cyntoia Brown could be a gifted litigator, professor Preston Shipp thought, as he discussed the moving parts of the criminal justice system with his 30 students. Inquisitive, engaged, able to parse a legal principle and trace its lineage, the 21-year-old Brown was unlike anyone he'd ever taught.

It wasn't just that she wrung every nugget of knowledge she could from her professor. It was her active, searching mind. Whenever Shipp played devil's advocate supporting the prevailing model of mass incarceration, Cyntoia was the one student he could count on to pick holes in his argument. That set her apart from his students at Lipscomb University, undergrads whose attendance at chapel and Bible study is mandatory.

But there was another reason Cyntoia was different. Unlike his Lipscomb students, whose futures were limitless, Shipp knew she would never become a litigator. That's because the class he was teaching met behind the heavy steel doors of the Tennessee Prison for Women, inside fences strung with razor wire.

By that spring of 2009, Cyntoia Brown had been locked up for nearly five years. Under the terms of her life sentence, she had about 45 to go before her term was up.

It was the second year of the Lipscomb Initiative for Education, a free program that places 15 traditional Lipscomb undergrads — mostly from white, upper-middle-class Christian families — in the same class with 15 felons, convicted of crimes such as murder and armed robbery. The program was intended to address gaps left after a 1994 federal law effectively defunded Pell Grants for inmate education, despite research from the Federal Bureau of Prisons showing that education lowers recidivism rates.

In 2004, Cyntoia was already a veteran of Middle Tennessee's juvenile justice system. Back then, she was living out of a room at a South Nashville extended-stay dive. Her companion was a 24-year-old drug dealer and armed robber known as "Cut-throat," who had her out on a Murfreesboro Road red-light district turning tricks for coke money.

That life reached its brutal apex on a summer night that August, when a 43-year-old real estate agent picked her up under circumstances that raise as many questions as they answer. That night, Cyntoia shot him in the back of the head and stole a couple of guns from his house. She was caught, and a jury convicted her of first-degree murder and especially aggravated robbery. At an age most kids are worrying about drivers' licenses and prom dresses, Cyntoia Brown was facing an adult criminal trial for premeditated murder.

But Preston Shipp didn't know any of this. To him, Cyntoia was a wunderkind in prison blues. For all her outsize garrulousness, she was just 5 feet 2. She wore her thick, wavy black hair just past her shoulders, and her large, expressive eyes were often rimmed with black eyeliner. She was a magnetic presence, even in standard-issue jeans with "Tennessee Prison for Women" stenciled down the leg.

Shipp was no stranger to the criminal justice system. A former Tennessee assistant attorney general, he often worked the other side in the Tennessee Court of Criminal Appeals, arguing on behalf of the state. If an appellant claimed his trial representation was ineffective, it was Shipp's job to argue that the defense was more than adequate. If an appellant claimed his sentence was unreasonable, Shipp argued it was appropriate and just.

During his five years in office, Shipp wrote some 250 briefs. He didn't lose much sleep over the people he helped keep behind bars. Most of them, he thought, were exactly where they needed to be.

But over the past few years, something had changed. He'd been spending time in the prison, teaching young women like Cyntoia who seemed eager to redeem themselves and their squandered lives. In class, he led his students in scathing critiques of the criminal justice system — the mass incarceration, the neglect of victims' needs, the damaged people who often ended up convicted, the lip service paid to rehabilitation.

Shipp began to question his long-held beliefs, and to wonder about people who'd once been nothing more to him than names on a docket. Then one day, in April 2009, about a month into class, the professor was sorting through his mail when something stopped him cold.

Among the letters was an opinion from the Tennessee Court of Criminal Appeals. It settled a case he'd argued the summer before. The judges upheld the trial court's conviction — which meant the professor successfully defeated the appeal on behalf of the Tennessee attorney general. It was another win for Preston Shipp.

Any sense of victory he felt, however, was gone when he read the appellant's name. It was an improbable coincidence, and yet there it was: the name of his star student, Cyntoia Denise Brown.

Shipp sat frozen in disbelief. Could the polite, intelligent, unfailingly thoughtful girl who showed such promise in his class be the same cold-blooded murderess whose appeal he helped crush without a second thought?

In time, he would learn a lot about Cyntoia. He would find out about the depraved state the girl was in at the time of the murder. He would discover the things that had been done to her, and why she might reasonably think a stark naked 43-year-old man would go for a gun when she refused his advances.

Before knowing any of this, though, Shipp had successfully argued against her. At root, he had stated unequivocally that she deserved to remain in prison — for most, if not all, of her life.

The problem, Shipp says today, is that the system leaves no room for rehabilitation — and no chance for the juvenile court to reappraise troubled teens who become sensible adults. Like Cyntoia, juveniles convicted of serious crimes are being tried as adults with increasing frequency. Faced with a resource-strapped Department of Children's Services and a jurisdiction not to exceed a youth's 19th birthday, juvenile judges are left with little choice but to ensure public safety by locking them away — even if that finishes off a life already damaged by abuse, neglect and circumstance.

Upon receiving the letter, Shipp now had to face his most promising pupil. For when Cyntoia got word that her appeal was denied, she would learn that the instructor nurturing her hopes — of salvaging the life she threw away at age 16 — was the same person who had helped end them. It was as if a door finally slammed shut — a door that started closing before she was born.


Ellenette Brown, who is black, had no clue 16-year-old Georgina Mitchell, who is white, was pregnant. How could you tell? In 1987, all the kids were wearing baggy football jerseys. Georgina's was certainly roomy enough to hide a swelling belly.

But there were a lot of things Ellenette probably didn't know about the young woman who befriended her son, John Harleston. Georgina had come to Clarksville to live with her sister. Her mother warned her she could come back home to Georgia on one condition: without the black baby growing in her belly. Georgina never went home.

Instead, she began hanging around Ellenette's house, a gathering spot for neighborhood teens. Ellenette, a trim woman with finely boned hands, was a substitute teacher at a nearby elementary school. Kids like Georgina were drawn to her. They could talk to her about things they could never broach with their own parents.

But Georgina didn't tell Ellenette about the baby she carried, or the fifths of liquor she drained most nights. Nor did she mention the money she made charging for sex, or her family's history of suicides and mental illness.

On Jan. 29, 1988, Ellenette received a call from John. Georgina, he said, was in the hospital. Was she injured? Ellenette wondered. Her worry shifted to disbelief when he told her the girl was a new mother. By the time Ellenette and John visited Georgina in her room, she'd named her baby daughter Cyntoia. There was no father present. He could have been one of several men, including John Harleston, Cyntoia says, but Georgina could never be certain. Mother and daughter vanished shortly thereafter.

When Georgina showed up six months later on Ellenette's doorstep, with Cyntoia in her arms, it was to ask Ellenette to look after her baby for a while. Ellenette had no idea where they'd been, but she found Cyntoia such a sweet child that she didn't mind. The days stretched into weeks, the weeks into months. Ellenette grew to love the baby girl, to treat her like a daughter.

Yet caring for her was a struggle. Ellenette's husband Thomas Brown, an Army infantryman, was often deployed abroad. Ellenette couldn't stay home with her because she worked. Nor could she take Cyntoia to day care, because she had no birth certificate or papers of guardianship. Instead, she left the baby girl with an elderly neighbor she could trust.

Eventually, Ellenette obtained guardianship papers. In the eyes of the state, Cyntoia was now her ward. All seemed well and unusually stable — until a year later. Without warning, Georgina resurfaced in Clarksville.

The wayward mother asked Ellenette to get Cyntoia dressed. She told the girl's new legal guardian she was coming to pick up her daughter. When Ellenette told this to John Harleston, though, he gave his mother a different set of instructions.

Do not give her that girl, he said.

He had recently been corresponding with Georgina. In her yearlong absence, he'd learned, she had been hooking out of a motel on Trinity Lane. She was in and out of jail, strung out. So before Ellenette left for work that day, she instructed her husband not to let the child out of his sight.

That afternoon, Thomas called. He was frantic. Georgina had come by, saying she wanted to take Cyntoia shopping. She told him she'd bring her right back. He relented. Now they'd been gone for hours, Thomas said, and he'd been calling the phone number she left. No one answered.

Ellenette went to the Clarksville police and explained the situation. Georgina would surface at some point — most likely in jail — but what about Cyntoia? At this point, Cyntoia was 18 months old. Her guardian had no idea where to start looking, or even whom to ask.

Months passed. Ellenette lived in a state of perpetual worry, shedding weight she could ill afford to lose. Finally, one of Ellenette's neighbors stepped forward. It was Georgina's sister. She had been covering for her sibling, but she knew the strung-out mom couldn't care for the little girl. She told Ellenette that Cyntoia was in Georgia.

The trail led to the Elizabeth Canty Homes, a crime-stricken public housing development in Columbus, Ga. When Ellenette reached a man at the housing project's office, he knew exactly whom she was after. Georgina had been picked up a number of times for drugs and prostitution. She left Cyntoia with an elderly couple, and split. With an end to the ordeal in sight, Ellenette dispatched her son-in-law to Columbus with the girl's guardianship papers.

He arrived, but the news wasn't good. The couple would only relinquish Cyntoia if Ellenette picked the child up in person. Her desperate guardian didn't hesitate. She drove seven hours through the night. But when she met her son-in-law, and they arrived at the couple's home, Cyntoia was gone.

It had been six months since Georgina had taken her. Now the girl was 2, and Ellenette could only imagine what she had been through, the places her mother had taken her, the people she'd been left with. Ellenette went to the Columbus police, who informed her that Georgina was in jail. Meanwhile, the project's sympathetic HUD manager said he'd called around and had just located Cyntoia. She was fine and staying with another couple who had sheltered Georgina. Give them 30 minutes to dress Cyntoia, he said, and go get your child.

The police offered to escort Ellenette and her son-in-law into the projects. They told her white son-in-law to wait in the car. She knocked on the door. As she began explaining to the woman who she was, Ellenette's voice must have carried into the apartment. Tiny footsteps padded toward the door.

As quickly as her wobbling legs could carry her, the missing toddler locked her arms in a vise grip around her guardian's neck. Between wracking sobs, in a 2-year-old's halting speech, the girl asked why she'd left her. When she could finally speak herself, Ellenette explained she'd done no such thing. She had come to take her baby home.


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