As Circuit Court Judge Evelyn Baker stared down at Bobby Bostic in her St. Louis courtroom, she was filled with disgust. It was the winter of 1997. Bostic had been found guilty of committing a series of armed robberies in his own neighborhood when he was only 16. His victims had come to his side of town in a spirit of giving, carrying donations for Christmas. Bostic and his 18-year-old friend Donald Hutson had held them up at gunpoint. Two men in their 20s handed over their money but were shot anyway. The bullets grazed them, but they survived.
After being swiftly arrested, Bostic refused a plea deal, insisting on going to trial and pleading not guilty. The jury convicted him on 18 charges — a total of 241 years. The prosecutor asked Baker to impose them consecutively. “These were good-hearted people, all of them” he said of the victims. “And they ran into two mean-hearted men. They’re not boys, they’re men.”
Baker was not known for harsh sentences. In fact, she had a reputation for the opposite. The first black woman appointed to the Circuit Court bench, Baker was often accused of being soft on crime. She angered the St. Louis circuit attorney for throwing out felony convictions for lack of evidence. Her penalties in drug cases were decried as too lenient. Months before Bostic’s crimes, Baker had sparked outrage for sentencing a drunk driver who killed two teenagers to probation rather than prison.
But on that day, it was Baker who was angry. Bostic had stormed out of her courtroom after the verdict. He had shown no remorse. His mother had written a beautiful letter on behalf of her son. “Give him something that I can live with, please,” Diane Bostic had begged Baker that day. But Bostic had written to Baker, too. Several letters, in fact. They were supposed to explain his behavior, to show that he was smart and had potential in life. He quoted Marvin Gaye and Malcolm X and said that God was on his side. He also indulged in some shameless flattery. It didn’t work. All Baker could see was an arrogant punk who refused to take responsibility for his actions.
“Mr. Bostic, I sat through this trial, I saw your family every day of the trial,” she began. “I saw them beg with you, plead with you, try to convince you into entering a plea of guilty in a case in which the evidence was overwhelming.” Bostic had ignored them. “You don’t listen to anyone,” Baker went on. “You write me these letters. It’s the victim’s fault. It’s the police’s fault. It’s your mother’s fault. It is your fault. You put yourself in the position to be standing in front of me facing 241 years in the Department of Corrections. You did it to yourself.”
Baker would make an example out of him. “I hope this will be a message to the other young men and women out there,” she said. She imposed the sentences consecutively, the practical equivalent of life without parole.
“She took his life away,” Hutson told the St. Louis Post-Dispatch years later, in an interview from prison. He admitted that he had been the main aggressor on that day in 1995 — the younger Bostic was mostly following his lead. But Hutson had taken the deal that Bostic refused, pleading guilty in exchange for a 30-year sentence. He will be eligible for parole this year. Bostic, who turned 39 last month, will be parole eligible when he is 112 years old.
After more than 20 years in prison, Bostic now has a shot at a second chance. In December, the ACLU of Missouri submitted a petition for a writ of certiorari before the U.S. Supreme Court. It argues that Bostic’s sentence violates the Eighth Amendment ban on cruel and unusual punishment. In its 2010 ruling in Graham v. Florida, the court prohibited life without parole sentences for defendants convicted of nonhomicide crimes committed as juveniles. Not only are teenagers less culpable for their crimes than adults, the court ruled, they have a greater capacity to change.
The ruling in Graham was premised in part on neurological findings about the adolescent brain. They are fundamentally different from adult brains — and the areas responsible for such consequential matters as impulse and behavior control are not close to fully formed. Instead, they continue to mature through late adolescence and beyond. Like Bostic, the defendant in Graham was just 16. He did not kill anyone. He was set to die behind bars until the Supreme Court ruled in his favor. Yet, while the decision raised the prospect of freedom for Graham and others serving life without parole for nonhomicide crimes, it did not apply to Bostic, who was serving a term of years.
In reality, it is a distinction without a difference. As Bostic’s lawyers point out, Baker made her intention all too clear at his sentencing. “Bobby Bostic, you will die in the Department of Corrections,” she said. His mandatory parole hearing would not come until the year 2201. “Nobody in this room is going to be alive in the year 2201,” Baker added. Eight years after Graham, Bostic has lost repeated attempts to appeal his sentence. Yet, his lawyers argue, “not a single Missouri court has even issued an opinion, explaining how [his sentence] can be squared with this court’s decision in Graham v. Florida.”
Bostic has attracted strong public support. The editorial board of the Post-Dispatch recently described his sentence as “inhumane.” In late January, a group of 26 former judges and prosecutors signed an amicus brief in support of Bostic, brought by the Phillips Black Project, a nonprofit law firm. An accompanying press release quoted Graham’s holding that states must provide a “meaningful opportunity to obtain release based on demonstrated maturity and rehabilitation.” Boston’s case “exemplifies” this requirement, according to Jennifer Merrigan, counsel of record for the amici.
Baker, who retired 10 years ago, was not among the former judges and prosecutors joining the amicus brief. But this week, she spoke publicly about Bostic for the first time, from her home in St. Louis. “As the sentencing judge,” she told me over the phone, “I hope they release him.”
Baker remembered Bostic’s case “like it was yesterday,” she said. “It sticks out because he was so young.” Although he had not killed anyone, she felt he might, eventually. “This young man came off as being a total sociopath at the time.” Baker said she does not regret sentencing him so harshly.
Yet Baker is also aware that Bostic has made efforts to change behind bars. She recalls a newspaper article that described his many certificates earned and courses completed in prison — a fulfillment of what he had vowed to do in one of his letters, to use prison “as a higher institute of learning.”
What’s more, Baker knows about the modern scientific evidence underpinning Graham, which showed that the adolescent brain is “not fully cooked,” as she put it. “That was not information that was available when I sentenced Bobby.” Back then, a juvenile was “a mini-adult.”
I asked Baker if knowing this would have led her to handle his case differently. “If I knew then what I know now, of course I would have.”
A scene outside the 22nd Judicial Circuit Court in St. Louis, Missouri.
UIG via Getty Images
Baker is not the first person involved in the trial to acknowledge the harshness of Bostic’s sentence. In 2014, one of his victims spoke to the Post-Dispatch anonymously as part of an in-depth feature on the case. “People who have committed heinous crimes — murder and rape — are getting a lot less of a sentence,” she said. Still, the crime had left lasting scars. The woman did not wish to be named due to her “continuing fear” of Bostic.
A crime does not have to be lethal to leave trauma in its wake. While no one was killed that day in 1995, somebody certainly could have been. And the teenagers’ actions had been undeniably cold-hearted, a betrayal of their community.
At around 5:30 p.m. on December 12, 1995, a group of people had arrived on McRee Avenue, on the west side of St. Louis. The Post-Dispatch had recently published its longstanding annual series the “100 Neediest Cases.” Over several issues, the newspaper had profiled families and individuals who were among the city’s most vulnerable, calling for donations, which would be administered alongside the United Way of Greater St. Louis. “Reading about children and men and women who live this close to us — but in circumstances sometimes impossible to imagine — can break your heart,” the series read that year, urging people to help.
The group on McRee Avenue had heeded the call. They were coworkers, ranging from 21 to 40. Their company had “adopted” one of the families profiled — a single father with three young children. They were bringing a Christmas tree and some presents, along with a donated couch. Linda Schaar was taking the cushions from her trunk when Bostic and Hudson walked toward her. Bostic pointing a gun at her, she would later testify at trial. “He told me to give him all of my money or he was gonna shoot me.”
Schaar’s boyfriend, Christopher Pezzimenti, jumped out of his truck, yelling. Bostic demanded money — he gave him $500. Then, “he shot me in the side,” Pezzimenti would testify. Another man, Matthew Leo, was shot by Hutson. Police would say the men were partly protected by their thick winter coats.
It did not end there. Within an hour, and mere blocks away, Bostic and Hutson held up a 28-year-old woman named Regina Davis. She too was making charitable donations, delivering toys. They forced her into her white Volvo. Hutson put a gun to her head and “told me to take my earrings off, take my coat off. He was asking how much money I had,” she testified. She gave him her purse, but Hutson wanted more. “So he put his hands in my pants to check to see if I had some money down in my drawers.” Davis said she was afraid he would rape her, but Bostic convinced Hutson to let her go. She ran to a barbershop and called the police.
The armed robberies were front-page news in St. Louis. They even brought bad publicity for the donation drive. One victim was upset that no one had warned them that it was a “bad neighborhood” before they went in. “We had no clue,” she told the Post-Dispatch. “Later, the police said we were stupid.” Hutson’s defense attorney recalled the crime as “rather notorious at the time because these people were just out delivering Christmas gifts to underprivileged people when they were assaulted and robbed. I think, as defendants, these two were very much hated.”
Yet, lost in the outrage was that Bostic himself could have been included alongside the “neediest” families profiled that year. He had grown up in a fraught environment, in a neighborhood rife with poverty —and rooted in legacies of racism and housing discrimination. In segregated St. Louis, “there’s a clear divide, and everyone in the city knows the street that divides black and white and poor and middle class and rich,” says Bostic’s ACLU attorney, Anthony Rothert, who has lived in the city for decades. “Bobby was raised on the wrong side of that divide.”
In a 2013 letter seeking clemency from Gov. Jay Nixon, Bostic’s older sister Marquise described some of the family’s struggles. Their mother had her first child when she was a teenager. “When things got hard she’d turn to drugs and alcohol which would make life hard for us,” she wrote. “There were times when Bobby would have to go out to steal food for us to eat.” Instead of eating his school lunch, he would bring it home to his family. Bostic’s brother Michael explained in a separate clemency letter that the family was technically homeless at times, staying with various relatives. His father was not in the picture. Bostic was “often angry and unstable,” he wrote.
Bostic began experimenting with drugs and alcohol starting when he was about 10 years old. At this time, crime was on the rise in St. Louis. In 1991, local media tracked an uptick in violent crime, with frightening projections described as “a demographer’s nightmare.” Baker, who was a juvenile judge at the time, told the Post-Dispatch that teenagers needed a wake-up call. Maybe they should watch an autopsy to grasp the consequences of their actions, she said. “Let them see a face being peeled off,” she said. “Let them see how terrible, how disgusting it is. Let them see the entrance and exit wounds.”
“We were terrified of juveniles back then,” recalls Michael Wolff, former chief justice of the Missouri Supreme Court, who is now dean emeritus at St. Louis University School of Law. Although crime was certainly a problem, the heated political rhetoric at the time offered only punitive solutions. “Juveniles are dangerous and you’ve got to lock them — and maybe lock them up forever.” This was the era of the “superpredator” — a racist myth that led a generation of youth offenders to be given the harshest sentences in the world. It was also in this era that a different Missouri youth — a white teenager named Christopher Simmons — was sentenced to die for a murder committed at 17.
The Simmons case would set the stage for the Supreme Court’s ruling in Graham. In 2002, the Missouri Supreme Court stayed Simmons’s execution pending the high court’s decision in Atkins v. Virginia, which ultimately declared the death penalty unconstitutional for people with mental disabilities. The Missouri Supreme Court then overturned Simmons’s death sentence, with Wolff joining the majority. In 2005, the U.S. Supreme Court upheld the ruling in its historic decision in Roper v. Simmons, which abolished the death penalty for juvenile defendants nationwide. This would kick off a trend in the court’s rulings on juvenile sentences, extending the logic undergirding Roper — that “as any parent knows,” youth are more reckless and less cognizant of the consequences of their actions, and more susceptible to influence from others. Five years after Roper, the court decided Graham, invalidating life without parole for teenagers who committed nonhomicide crimes. Another landmark ruling followed in 2012: Miller v. Alabama abolished mandatory life without parole sentences for juveniles. And in 2016, in Montgomery v. Louisiana, the court ruled that Miller should be applied retroactively.
Back in his Missouri cell, however, Bostic remained stuck. Even as states were forced to respond to the Supreme Court’s rulings — scheduling resentencing hearings, or changing the law — his case fell through the cracks. In its 2014 report on his case and others, the Post-Dispatch found Bostic “is serving the longest sentence of any juvenile offender in the state, not counting the 81 murderers who could get reconsideration under the Miller ruling.” There were three other men serving sentences longer than 100 years, but they had committed murder.
Bostic’s petition is not the first of its kind. “Different states have ruled different ways on the issue of whether an effective life sentence like this constitutes an unconstitutional life sentence,” Rothert explains. “Usually, when there’s a split in authorities, those are the kind of cases the Supreme Court takes. However, it hasn’t taken any of the previous ones that went one way or another on this issue. We don’t know why. Some day, this is an issue that the Supreme Court will have to resolve.”
Wolff, the sole Missouri name on the amicus brief in support of Bostic, says his case has “systemic importance.” It is inconceivable that the court intended for a 241-year sentence to be treated differently from the life without parole sentences it banned in Graham and Miller, he says. The lack of resolution means states can continue to circumvent the rulings, by handing down similarly draconian sentences. “If the court is serious about enforcing its judgments, it probably should take this case.”
Bobby Bostic’s certificate in basic business studies from Missouri State University.
Photo: Free Bobby Bostic
In her 2013 letter on her brother’s behalf, Bostic’s sister did not dispute what Baker said as she scolded Bostic back in 1997: He did blame their mother. And he did not show remorse — “or even know what remorse meant.” But her brother is a different person today, she wrote. After their mother died of cancer in 2000, his attitude changed. He wrote a book about their family called “Dear Mama” and became a prolific writer. “He has also written poetry that my daughter uses for motivation,” she wrote. One of Bostic’s recent essays, about a prison garden, was published in Farming Magazine.
There is also a lot of writing on Bostic’s behalf: a clemency letter from a business professor at Missouri State University calling him an “excellent student who cares about his future”; another from a vice president at Regions Bank in Springfield impressed with his “strong sense of entrepreneurship.”
Rothert, the ACLU lawyer, says Bostic has also done a “remarkably good job” in his pro se filings. While he has had other attorneys from time to time, for the last several years, “he was representing himself and filing his own petition or his own pleadings.” It was only last year that the ACLU received a letter from Bostic seeking representation. “He got most of the way here on his own.”
Baker retired in 2008, two years before the Supreme Court made its decision in Graham. After 25 years on the bench, news articles memorialized her as “feisty.” On the phone, Baker was frank about the discrimination she experienced as a black woman judge. She was also blunt about the racist double standards she saw in her courtroom. “Many times I could have gone on the bench with a blindfold and, based upon the states’ recommendation, I could tell you the race and gender of the defendant,” she told me.
Still, Baker is proud of her time on the bench. “I think I was able to do more good than evil. Because I actually considered every person who stood in front of me as an individual. Probably one of my greatest regrets is that we had to sentence so many people [with] serious psychological problems,” she said. This included Bostic. “Bobby was probably a traumatized child. He was still dangerous, but I think Bobby was in serious need of some type of psychological treatment. That’s my opinion now. It was not my opinion then.”
I asked Baker what she would say to Bostic now. She briefly paused. “I hope he gets out,” she said. “I hope he’s learned something. I hope he has a chance to live in the real world, continue with his education, have a family, get a job, have a mortgage. Have a chance to have a life. He’s grown up in prison.”
Top photo: Bobby Bostic in the visitation room at Crossroads Correctional Center in Cameron, Mo., on July 10, 2014, where he has served almost 20 years of a 241-year sentence.
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