As the nation’s highest court prepares to hear oral arguments today on the constitutionality of sending juvenile killers to life in prison with no chance for parole, an unlikely trio of Bostonians is hopeful the justices move quickly to abolish the sentence.

“I would give my life for Hassan and he would do the same for me,” said retired Massachusetts Juvenile Court Judge Mark E. Lawton, speaking about a teenage killer he sentenced more than 20 years ago – but has now become Lawton’s close friend.

“If he were the devil incarnate I wouldn’t have anything to do with him, but he is a great tool for goodness,” Lawton said last week, as he prepared to introduce Hassan Smith, now 40, to his juvenile law class at New England School of Law in Boston. Smith, now a father of three who mentors troubled inner-city youth, believes firmly teenagers - like the one he once was – deserve a chance at redemption no matter how serious their mistakes.

It is that very question the high court is being asked to rule on in the appeals of two-14-year-old killers. Like Smith, who was 16 when he shot Jeffrey Booker in Boston, both inmates are black.

One of those defendants, Evan Miller, from Alabama, was 14 in 2003 when he and an older boy fatally beat a drunken neighbor to death in a trailer park, lit the victim’s home on fire and fled. The second defendant appealing to the high court, Kuntrell Jackson, was convicted in a 1999 armed robbery in which another youth fatally shot an Arkansas convenience store clerk.

Both Miller and Jackson were sentenced to life without parole. Their lawyers argue the court should build on its own recent decisions outlawing other harsh sentences for juvenile offenders, like the death penalty and life without parole for non-homicides. The court has relied, in part, on scientific studies demonstrating young teens are less able to control their impulses or realize the devastating consequences of their choices at the time of the murder.

A ruling is expected in June.

“Don’t put these children in jail for life”

Hassan Smith knows how deeply fortunate he has been in avoiding the same fate as Miller and Jackson.

He was tried in Massachusetts juvenile court when the harshest sentence he could get for murder was a commitment to the state Department of Youth Services until he was 21. In 1996, a high point in Boston’s juvenile crime rates and following an especially brutal slaying by a teenage altar boy, Massachusetts passed legislation mandating youths over 14 convicted of first-degree murder should be jailed for life without parole.

“Those laws scare me,” Smith said. “I am very, very sorry for what I did when I was 15.”

Seven youths – all but one minority – have received the sentence in Massachusetts, the only New England state to impose the harsh punishment on defendants as young as 14.

“If the laws then were as they are now the world would have lost a very positive, loving human being,” said Lawton, a former legislator who spent 27 years on the bench.

Both Smith and Lawton, who reconnected by chance in 1992, are outspoken advocates against the sentence and for a proposed reform effort underway in the Bay State to allow those defendants parole eligibility after 15 years. They are joined by the woman whose life Smith destroyed in 1988 when her son was fatally shot outside her Roxbury church. Jeffrey Booker was unarmed and 21, the father of a year-old son and an aspiring cellist.

“Don’t put these children in jail for life. No, no, no,” says 79-year-old Sonia Booker. “It’s not going to bring my son back. Nothing is ever going to bring him back.”

Booker said she has never been asked before about the life without parole sentence.

“There is a chance for these children to be redeemed,” she said of teen killers like Smith.

“It’s not up to me to keep revenge”

Booker, a former elementary school teacher and pianist, disputes Smith’s claim he has sought her forgiveness, though she said she would give it if he asked.

Sonia Booker grew up with Smith’s family and was close friends with his mother , Elizabeth Smith, now 73.

“It’s not up to me to keep revenge. When my son got shot on Father’s Day, I had to walk by myself and ask the Lord to show me the way to forgive,” Booker said.

“His mother is a beautiful person. I don’t believe in holding no anger in my heart. You can kill your own self doing that,” Booker said.

Massachusetts prosecutors, who have charged more than 60 youths aged 14 to 16 with murder in the past 15 years, firmly believe the law should not be changed. In a report issued last fall, the Massachusetts District Attorney’s Association argued teenage murderers should not get “leniency and mercy that they never showed their victims.”

The MDDA also claims prosecutors are judicious in their use of the first-degree murder charge, given only seven Massachusetts youths have received the sentence to date.

But to sitting Juvenile Court Judge Leslie E. Harris, who has handled teenage murder cases, people like Smith deserve a chance to prove they are sorry.

“Hassan has tried to be a different person, has tried to be a role model,” Harris said. “I don’t believe in throwing away any child.”

“We should hold him accountable, for sure. Hassan should never forget what he did, but that doesn’t mean we should ever forget about him,” Harris said.

Harris points to a current Michigan case in which a 13-year-old could be sentenced to life without parole for a drug-related slaying committed by his estranged father, whom he had just recently reconnected with.

Charles Lewis Jr. was in a car with his father and a group of his father’s friends in 2010 when they kidnapped a rival’s girlfriend and Lewis Sr.’s gun fired accidentally, fatally wounding the victim.

“All I could think about were the kids I see who come in front of me – 13, 14-year-old kids charged with shoplifting, shooting a gun. Who they are at 12 is not who they are going to be at 28 or 30,” said Harris, who regularly speaks to state prison inmates.

“We still have this mentality that children are monsters and they are not,” Harris said. “We have some monstrous cases, but they are the exception, not the rule.”

Harris, like Lawton, has connected with a defendant whom Harris sentenced to five-to-seven years in a shooting. The bullet did not hit anyone.

“This was a child that was giving up on himself. Before he left the courtroom, I told him he couldn’t give up on himself. This didn’t have to define him for the rest of his life,” Harris said.

Harris, who has two grown sons, said as a teenager he might have made different choices than he would today.

“If I were provoked, I’d run because I want to be there for my kids. When I was younger, I might not have run so quick and that is the difference.” Lawton agrees.

“No one seeks to demean the Bookers. The transcendent tragedy is the loss of life,” said Lawton. “But in all of these matters there are corollary tragedies. Unfortunately this is a tragedy that will follow Hassan for the rest of life.”

For Lawton, the inconsistency in how juveniles have been sentenced for murder in Massachusetts indicates one of the dangers of the mandatory punishment.

Last year, the New England Center for Investigative Reporting found the sentence was being applied inconsistently and unfairly to teens charged with murder. In some cases teens who committed more violent and grisly slayings than those convicted of first-degree murder, were able to plead guilty or obtain second-degree convictions, making them parole eligible, NECIR found.

“You can take a truly heinous crime, charged as murder one, and because of some evidentiary weakness that defendant can apply for parole in 15 years,” Lawton said.

“I had never been called ‘son’ by a white man”

Smith has struggled to remake his life after the “horrible mistake” he said he made nearly 24 years ago.

Raised in the housing projects, Smith got his first gun at 12; sold cocaine and marijuana, was kicked out of school and fell into gang life. He said he feared for his own life on the day of Booker’s death, which Lawton said was triggered by a gang dispute.

“In Hassan’s neighborhood, to carry a gun was a necessity; it was part of the neighborhood culture,” Lawton said.

Lawton remembers the moment when the jury found Smith delinquent of murder.

“I remember looking at Hassan and he looked at me. I said ‘I wish you all the luck in the world,’” Lawton said.

Those words meant something to Smith.

“I took them to heart. Judge Lawton called me ‘son’ in the courtroom. He treated me with respect. I had never been called ‘son’ by a white man before; ‘boy,’ yes, but that is a racist term,” Smith said.

After finishing his DYS commitment, Smith moved in with a foster mother in Northampton to escape the crime-ridden Boston streets and earn his high school diploma. He took college courses and was looking for work when he spotted Lawton on a city subway car in 1992. Tapping him on the shoulder, Smith asked Lawton, who was on his way to preside over a Cambridge jury trial, if he remembered him.

The judge did not.

When Smith reminded him, Lawton asked what he was doing with his life and Smith responded: “I’m looking for a job.”

The judge’s invitation for a cheeseburger lunch a few weeks later sparked a warm friendship that has spanned two decades. “He’s like a little brother to me,” Lawton said.

The pair often eats dinner together, visit one another’s homes and have met each other’s children in the intervening years. Lawton helped Smith find a job as a prison guard at the Suffolk County House of Correction, where he worked for ten years.

But there have been struggles.

Smith’s bid to become a Boston Police officer in 1997 was rejected by the then-commissioner because of his juvenile record. Smith was let go from his corrections job after sexual harassment charges were filed against him in 2003. A five-year relationship with a woman he met in an emergency medical technician class ended badly in 2005. The guardian ad litem sorting out the couple’s custody issues credited Smith for his parenting skills and diligent financial support of him and his girlfriend’s two young boys.

Smith has since worked as a skills trainer with the disabled at the Boston Center for Independent Living and ran unsuccessfully for Suffolk County Sheriff in 2010.

“I’m proof the system worked”

Still, Smith points to the irony of a sealed juvenile record that continues to haunt him.
“I’m proof the system worked. The purpose behind the sealed juvenile record is that it doesn’t hinder my future,” Smith said.

Today, with a daughter in college and two boys, Smith spends his time mentoring youngsters at risk of straying down a path of drugs, crime and guns.

“I tell them: it’s not how far you fall, it’s how far you rise,” Smith said, pressing the kids to avoid dependence on using race as an excuse for their troubles.

“The marching era is over. It’s time we do for ourselves,” he said.

“He talks about the harm and the pain you can cause. That type of empathy, concern and love you rarely see in some of our best citizens,” Lawton said.

Smith credits his own mother with doing her best as a single parent raising seven children in one of Boston’s toughest neighborhoods.

“She raised us with the best intentions. She put me in Kung Fu classes, tried to get me a big brother,” Smith said. “She would have turned me in if I hadn’t been arrested.”

Smith said he is deeply remorseful for the pain he caused the Booker family and has tried to prove it in the decades since the shooting.

“It’s one thing to say you are sorry; it’s another to mean it. I’m demonstrating I mean it,” he said.

As for his victim’s mother, she hopes the country’s highest court sees that children are not adults, despite terribly bad decisions they make as teenagers. She includes Hassan Smith in that group.

“That boy don’t know what he took away from me when he took my son away,” Sonia Booker said, remembering the murder trial decades ago. “I had to sit there and think about why this boy killed my son; it was a hurting thing but the hurt goes away and love comes in. I wouldn’t mind talking to Hassan if he would come.”

The New England Center for Investigative Reporting is a non-profit investigative newsroom at Boston University.

This is a follow-up report to the center’s 2011 investigative series on juveniles serving life without parole in Massachusetts.