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Black Man Sentenced to 241 Years In Prison Now Free on Parole with Support from St. Louis Judge Who Sentenced Him When He Was 16

A retired St. Louis judge, who sentenced a 16-year-old boy to almost two-and-a-half centuries in jail for a robbery, has since changed her mind, calling her decision an act of “insanity.” After leaving the bench, she dedicated her time to helping the young man, now 43 and a different person, get parole just in time for the holidays.

Man sentenced 241 years judge helps
Bobby Bostic sits with judge who initially sentenced him to 241 years. (CBS News Screengrab)

On Wednesday, Nov. 9, Bobby Bostic became a free man. It was the first time he was not a ward of the state since 1995. In 1997, then-Judge Evelyn Baker convicted him to 241 years in prison on 18 counts, with convictions for every count to run consecutively, for being an accomplice in two armed robberies.

Under her sentencing, he would not have been eligible for parole until he turned 112, according to the St. Louis American.

But Baker had a change of heart, now believing she was wrong and cruel to issue such a harsh sentencing on a young boy.

She said in 1997 at the sentencing, “Your mandatory date to go in front of the parole board will be the year 2201. Nobody in this room is going to be alive in the year 2201.”

In an interview with CBS’s “48 Hours,” she spoke about working the last four years to secure his freedom, regretting her use of that power she yielded with her robe and gavel. Baker even went before the state parole board on his behalf and lobbied for him, with a new understanding of juveniles who commit crimes.

“I don’t know if it ever happened before, but it was something I wanted to do,” she said. “’Cause, it was time for Bobby to come home and be with his family. He wasn’t the kid I sentenced. The Bobby Bostic I put in prison is not the Bobby Bostic who got out. Bobby did what many people can’t do. He created himself.” 

In Baker’s mind, Bostic wasn’t capable of reform. Baker says her sentencing reflected her lack of understanding about adolescent development. A teen’s brain, as research such as that by the National Institute of Mental Health indicates, is not fully formed until the mid to late 20s.

“Bobby should’ve had a chance,” Baker said. “I had no awareness at that time that Bobby, by being certified to be tried as an adult, did not become an adult. He was still a 16-year-old boy.” 

She wrote in an essay for The Washington Post, “What I learned too late is that young people’s brains are not static; they are in the process of maturing.”

“Two hundred and forty-one years is insanity when I think back on it,” she admitted in a CBS interview. “And I’ll say it right now: it’s insanity. He was a kid. He was a little boy.”

On Tuesday, Dec. 12, 1995, Bostic and another teen named Daniel Hutson were drinking gin, smoking weed and smoking PCP before deciding to rob a group of six at gunpoint. In a BBC interview, he said he knew the good samaritans were not from his neighborhood. It turns out they were en route to deliver Christmas presents to a family in crisis, as a part of a newspaper appeal.

“We saw the victims,” said Bostic. “We knew they weren’t from that neighborhood. They had a lot of stuff on their truck.”

According to sources, the group had two carloads and a truck with tons of gifts, including a Christmas tree and an old couch.

“It wasn’t a plan,” said Bostic. “We saw them. I looked at him [Hutson]; he looked at me, a knowing look. It was just an instant thing. We pulled the guns out.”

The prosecution alleged Bostic shot a bullet that grazed the victim before he and his friend carjacked and robbed a woman. After taking the woman’s leather jacket, car keys and money and fondling her breasts, they released her. When asked why he shot the victim, Bostic said he had asked them for the money and punched him in the face. He thought he shot at the ground, and after that the guy gave him $500.

He said, “I can’t make excuses. I didn’t even know what I was doing. I wasn’t trying to kill the dude or hit him… I shouldn’t have done it, and I regret it.”

In 2022, Bostic boasted earning an associate degree and writing 15 books while incarcerated, including a biography of his mother.

He learned he also was resilient. In 2010, when the U.S. Supreme Court ruled to outlaw life sentences for people under 18 for non-homicide crimes but refused to hear his case in 2019, he did not shrink or give up.

He re-focused and worked with the American Civil Liberties Union and the Missouri Legislature to pass a law based on his case. This piece of legislation, pushed by Republican Rep. Nick Schroer of Missouri called “The Bobby Bostic Law” allows teens locked up essentially for life for crimes other than murder to have a parole board review after 15 years in jail.

The law was adopted in 2021, which helped put along his 2022 parole hearing and his freedom being granted.

In addition to Baker, the victims also had a change of heart. Not one of them opposed his release. One wrote a note to the Missouri parole board asking for him to be freed.

After being released, Bostic was met by a group of family and friends. There to greet him also was Baker. When asked if he harbored any ill will toward her, he said he did not but was grateful for her support.

“I’m a free man all because of you all who supported me,” he said upon release.

“While I cannot change what happened so many years ago,” Bostic said, “I will mentor and teach young people to take a different path than I did when I was a young child myself.”

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