The strange case of Bobby Bostic, the man handed a 241-year sentence for crimes he committed when he was 16

The strange case of Bobby Bostic, the man handed a 241-year sentence for crimes he committed when he was 16
(Source:Getty Images)

39-year-old Bobby Bostic has spent more time behind bars - 19 years - than the amount of time he lived in society as a juvenile at the time of his arrest in 1995. The US Supreme Court, the last bastion of hope for those fighting unjust sentences, declined to take up his appeal this past week and Bostic now faces the prospect of languishing in prison for the rest of his life.

What did Bostic do that appropriated a sentence as harsh as 241 years, that too for a juvenile? The winter of 1995, December 11 to be precise, is the day he probably looks back upon with a pained expression on his face and pangs of regret. Detailed in his website,, are the incidents of that fateful day and his struggle against the justice system ever since.

Bostic, along with associate 18-year-old Donald Hutson, was walking down the streets of an impoverished neighborhood in St. Louis, Missouri, when they chanced upon some people they did not recognize. Fearing little consequence, they came to a decision to rob the unsuspecting pedestrians. What followed was a spree of armed burglaries where they robbed two people, attacked, fondled a woman and stole her car, and shot at a man who was helping deliver Christmas presents to a family in need.


He was subsequently caught and slapped with two counts of first-degree robbery, three of attempted robbery, two first-degree assaults, seven counts of armed criminal action, and further charges of kidnapping. 17 in all due to accomplice liability. The only plea bargain he was offered was a live sentence, and seeing no other option, he took it. 

Tried as an adult, the jury found him guilty of all 17 counts. They recommended 30 years for the three robberies; 15 years for the first-degree assaults and kidnapping; and five to 10 years for the attempted robberies and armed criminal action charges. A total of 241 years which would either have to be served consecutively or concurrently depending on the judge overseeing the hearing, Evelyn Baker.

Before the sentencing was handed down, Bostic was given the opportunity to speak and make a case for himself. Addressing Judge Baker, he said: "Your honor, I feel that during my incarceration, I have learned my lesson from past crimes, and I feel that I deserve a time cut. I feel about the time I’m due when I am a prisoner, I'm gonna take a college course or whatever I can learn and rehabilitate myself back into society and be a productive person in the community."


An excerpt from the trial reported by the St. Louis Post-Dispatch shows that Baker was not pleased with Bostic's decision to decline the plea deal of a 'baby life sentence' of 30 years. She pointed out his history of arrests: assault, for which he was on probation, and a slew of juvenile offenses for which he had not been prosecuted yet, and swatted away his apology.

She said: "You don’t listen to anyone. You write me these letters. It’s the victims' 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. I feel nothing for you. I feel the same thing for you that you apparently felt for those victims and you feel for your family. Everything is about Bobby. Bobby, Bobby, Bobby."

A last-ditch plea had little effect and Baker sentenced him to die behind bars with the following words: "Mr. Bostic, you made your choice, you will live with your choice, and you will die with your choice because Bobby Bostic you will die in the Department of Corrections. Do you understand that? Your mandatory date to go in front of the parole is 2201, nobody in this room will be alive in the year 2201."


Bostic's sentencing in 1997 was a product of circumstance, as well as the social and political landscape in the US at the time. Violent juvenile crime was on the rise across the nation and in a bid to crack down, then-President Bill Clinton had announced a wide-ranging proposal to crack down on young offenders. Because Bostic and Hutson had targeted people out delivering Christmas gifts to underprivileged people to assault and rob, there was little sympathy for the two from either the jurors or the judge.

The salt in the wounds came in the form of Hutson's sentencing several months later. 18 at the time of the crime and tried as an adult, Hutson was sentenced to a relatively paltry 30 years for the same crimes; 210 years fewer than his younger co-defendant. Hutson even admitted to being the aggressor and instigator that night and said he felt guilty because 'I put him in that predicament in the first place.'

He was eligible to go home in eight years while Bostic remained behind bars serving his sentence of life without parole. The only difference between the two was that Hutson pleaded guilty and Bostic, whose attorney Richard Moran was known for getting good deals from prosecutors, tried his luck and went to trial.


One of the points of contention Bostic's lawyers often bring up while arguing his case is that Baker did not take rehabilitation into consideration while handing down the harsh sentence. Indeed, in 2010, the landmark Graham vs Florida case saw the Supreme Court rule that juvenile offenders cannot be sentenced to life imprisonment without parole for non-homicide offenses.

In June 2012, in the related Miller vs Alabama, the court amended their previous ruling to state that mandatory sentences for life without parole for juvenile offenders, even in the cases of murder, was cruel and unusual punishment and in violation of the Eighth Amendment to the United States Constitution.

In 2016, the Supreme Court declared the ruling retroactive to cases on collateral review as a "new rule of substantive constitutional law" in Montogomery v. Louisiana, meaning that Bostic's case should have been reviewed and his sentence amended.

His lawyers pointed to the increasing body of scientific evidence and research which recognizes that children at the age of 16 do not have fully developed brains. They cited numerous papers which recognized the cognitive differences between children and adults and stated that the last region of the brain to fully develop, the prefrontal cortex - responsible for governing the response to inhibition, self-control, anticipation of consequences, and logical decision-making - is not fully developed by the age of 16.


Across the US, many juvenile offenders are now getting second chances because of the Miller vs Alabama case, but because of mere a technicality, Bostic doesn't. He is serving what is referred to as a 'de facto life sentence,' - which isn't technically a life sentence but a series of sentences that technically adds up to one. The US Supreme Court has not addressed the issue, and though many states have, Missouri is not one of them. The state's courts and legislature are still struggling to come to grips with the original 2010 ruling.

Besides Bostic, just three other youth offenders are serving 'life sentences' that amount to greater than a 100 years. All three are killers, and one of them, Orlando Fields, was given 227 years - still lesser than Bostic's sentence - for a 2003 crime rampage that included a murder and multiple carjackings and shootings. Bostic will only be eligible for parole in 2089 when he is 110-years-old and while state law calls for a mandatory parole review after 75 years in prison, that doesn’t apply to Bostic; his two separate crimes, while tried together, were considered separate for parole purposes.


He was unlucky with Missouri's 2016 passing of Senate Bill 590 as well. The bill stated that "Any person sentenced to a term of imprisonment for life without eligibility for parole before August 28 2016, who was under eighteen years of age at the time of the commission of the offense or offenses, may submit to the parole board a petition for a review of his or her sentence, regardless of whether the case is final for purposes of appeal, after serving twenty-five years of incarceration on the sentence of life without parole." This meant that people who were sentenced to life without parole were eligible for a parole hearing after 25 years; there was no provision for a case such as Bostic's.


His sentence also violates the Convention on the Rights of a Child, a treaty to which every single nation on Earth is party to, except, of course, the United States. The treaty states: "Neither capital punishment nor life imprisonment without possibility of release shall be imposed for offenses committed by persons below eighteen years of age."


Bostic has been a model prisoner. During his extended incarceration, he has made every attempt to make amends and become a responsible, functioning member of the society in the hopes that he sees freedom one day. He has written letters of apology to the victims of his crime; he obtained his GED during the first year of his imprisonment; he earned a paralegal diploma and took a victim advocate course through Adams State College; he completed a course in non-profit management and grantsmanship; he established several blueprints for non-profit organizations for troubled teens and charity; and he has even written four non-fiction books and eight books of poetry.

Other than the obvious matter of his incarceration, it's not as if Bostic has not had his fair share of hardships, personal tragedies, and testing times either. A few years into his sentence, his mother Diane succumbed to cancer at the age of 42. Not much after, his younger brother Shawn died due to complications of a gunshot wound that had left him paralyzed 10 years prior. Despite the adverse circumstances, he has remained eternally optimistic.


Many across the country feel that his sentencing is unfair and unjust, including one of his victims from the day. Unnamed, the woman said she was shocked to learn about his 241-year sentence. She told the Post-Dispatch: "People who have committed heinous crimes - murder and rape - are getting a lot less of a sentence. What he did could have been worse, but at the end of the day, you are tried for the crime you committed."

Even Baker herself admitted that her sentencing was too harsh. She wrote for the Washington Times: "I am now retired, and I deeply regret what I did. Scientists have discovered so much about brain development in the more than 20 years since I sentenced Bostic. What I learned too late is that young people’s brains are not static; they are in the process of maturing. Kids his age are unable to assess risks and consequences like an adult would. Overwhelming scientific research shows that children lack maturity and a sense of responsibility compared with adults because they are still growing. But for the same reason, they also have greater capacity for reform."


After Baker's advocacy for his release, he was offered an additional ray of hope when 75 prominent leaders in the criminal justice community - including former Acting Attorney General Sally Yates, former U.S. Solicitor General Kenneth Starr, and former FBI Director William Webster - called on the Supreme Court to grant him clemency by writing a brief which stated that his sentence violated his Eighth Amendment right.

However, that hope was short-lived. The Supreme Court turned down his appeal, with justices leaving the 241-year sentence in place. While his attorneys argued that the prison term violated the Constitution's ban on cruel and unusual punishment, Missouri Attorney General Josh Hawley said a 2010 Supreme Court ruling that outlawed life sentences for people under 18 who didn’t kill anyone applies only to a sentence for one crime.

Tony Rothert, the legal director of American Civil Liberties Union (ACLU) of Missouri, expressed his disappointment but said he was not surprised: "It’s extremely disappointing, of course, because we know and care about Mr. Bostic. But the Supreme Court takes very few cases, and often lets issues percolate in the states for many years before resolving conflicts."


One of his last hopes will be to seek clemency from Missouri Governor Eric Greitens, failing which Bostic will most likely die in prison for a robbery he committed when he was 16-years-old.

Share this article:

 Bobby Bostic St. Louis 241-year sentence crime