Trouble has always clung to Csean Skerritt.
It started early, with a middle school suspension for bringing a knife to class. Then came a suspended sentence for carjacking and assault and battery with a baseball bat. That was followed by a shoplifting spree at a Somerville Walgreens on a weekday morning in 2005.
When a store employee confronted him over the stolen candy, soda, and condoms, Skerritt — then 16 — whipped out a knife and stabbed the man in the chest as witnesses looked on.
The boy’s rationale for the near-fatal attack: “Wasn’t his day,” Skerritt later told a probation officer.
In the years since, Skerritt has assaulted correctional officers, dodged a cocaine trafficking charge, and escaped from youth detention workers. He has beaten a murder rap, bragged about his violent exploits, and survived gunshot wounds to the chest.
Clinicians at a youth detention center, court records show, suggested he may have rage disorder. Others have described him as ruthless, remorseless, empty.
Then, in perhaps his most confounding alleged crime to date, authorities say Skerritt approached baby-faced 13-year-old Tyler Lawrence on a Mattapan street on a Sunday morning in January. Skerritt, authorities say, shot the eighth-grader in the head not far from the home of his grandparents.
Despite his many travels through the criminal justice system, there’s no easy answer as to why he was free to walk the streets that day , how he skirted more lengthy prison sentences, according to The Boston Globe’s exhaustive review of court files. In some cases, he was a juvenile. Other times he was acquitted, and one time prosecutors dropped a case against him before trial.
The motive in the attack on Lawrence has eluded authorities. Suffolk District Attorney Kevin Hayden has gone so far as to acknowledge that prosecutors may never know what exactly transpired. Hayden initially said the shooter appeared to target Lawrence, but later clarified his remarks and added that the 34-year-old felon and the Norwood middle school student appear to have no connection whatsoever. Skerritt was indicted by a grand jury last week, but details of a possible motive have yet to emerge.
The shooting death of a child — for no apparent reason and with no apparent motive — has shaken the city like few other crimes in modern times. It has sparked memories of Darlene Tiffany Moore, a 12-year-old girl killed by a stray bullet in 1988 as she sat on a mailbox in Roxbury. And it has cast a harsh light on the criminal justice system, and the man who is once again behind bars — and once again linked to a fatal shooting.
For weeks, Globe reporters pored through criminal court filings that cover three decades and span Skerritt’s life. Together, the material amounts to a dark portrait stretching from his days as a troubled youth, through his teenage fascination with Boston street gangs, and, later, his brushes with fatal violence. He bounced in and out of jail, served short prison sentences, and at times skirted more serious sanctions.
Within his court files are letters to lovers, advice to friends, outbursts of anger, and the ruminations of a man who prided himself on a strict adherence to street code.
“I am who I am — a gangsta,” he wrote to a friend in 2015. “But also a good man. I have enough heart to feel.”
Alexander Skerritt didn’t know how, exactly, his only son had broken bad, only that it had happened.
His son, he told a probation officer in 2006, grew up in a stable, two-parent home in Dorchester. There were chores and curfews. School work and respect for others were ingrained early. As a child, Csean liked professional wrestling and play-fighting with his father, court records show, sometimes crying when he lost. He had good friends, was close with his sister.
But the boy transformed as he entered his teenage years.
“It was like overnight he changed,” Alexander Skerritt told the probation officer, “and all the good friends went away.”
In 2005, his father told a psychologist that his son spent a lot of time with members of a Boston street gang, according to a report filed in court, which noted that five or six of his peers had been killed in recent years and one had been ordered to serve 25 years in prison for kidnapping.
His family noted a history of anger. Two separate clinicians identified signs of intermittent explosive disorder, defined by the Mayo Clinic as sudden and repeated episodes of “impulsive, aggressive, violent behavior or angry verbal outbursts . . . grossly out of proportion to the situation.”
Though he could be deeply protective of those close to him — he once vowed to make sure his mother moved out of the city because he felt it was too dangerous, court records show — Csean Skerritt seemed to possess little empathy for anyone else.
Ariful Matubbar, a Bangledeshi immigrant, was working at a Walgreens in Somerville in 2005 when he narrowly survived an encounter with Skerritt.
Matubbar spotted two teenagers stuffing condoms and candy into their pockets and Skerritt left the store without paying for the items, according to court records. Matubbar followed him.
Outside the store, Skerritt confronted Matubbar and plunged a three-to-four-inch knife into his chest, piercing his lung. Skerritt then showed Matubbar the knife and started laughing, prosecutors wrote in court filings. Matubbar, who played soccer professionally in Bangladesh, needed more than 40 staples in his chest to treat his wounds.
“I came back from — literally — from the dead,” said Matubbar, now 42, in a Globe interview. “He tried to kill me.”
Matubbar lived in fear for years afterward because of the incident, he said, and struggled to find suitable work. At a court hearing, Matubbar said Skerritt’s mother apologized to him — but her son never did.
“His mom said he’s sorry and he can’t control his temper,” said Matubbar.
An attorney for Skerritt declined an interview request, as did his grandmother. A woman who answered a phone linked to Skerritt’s mother hung up on a reporter. Meanwhile, messages left with Skerritt’s father, Alexander, went unanswered.
Maura Driscoll, a licensed social worker who worked with Skerritt after the 2005 stabbing, saw small signs of hope. Though she described Skerritt as manipulative and unrepentant, she also praised his engagement in a substance-abuse treatment program and his willingness to seek help, according to a 2006 report filed in Middlesex Juvenile Court.
To her, it seemed the teen stood on a precipice, battling dueling identities: Is he a street tough child or a good kid?
Others were far less optimistic.
“He has no remorse,” the juvenile court judge in the Walgreens stabbing wrote in court filings.
“He will do the same thing when released,” Matubbar wrote in a victim impact statement.
In a presentencing report, which strongly recommended Skerritt be sentenced as an adult and to the full extent of the law, probation officer Timothy M. Carey shared a warning that would prove, in the years to come, chillingly prescient:
“This officer is concerned that should Csean Skerritt be released from his detainment on his 21st birthday the community at large would be in danger.”
The judge ultimately ordered Skerritt committed to a juvenile detention facility until his 21st birthday and added a provision that would send him to an adult jail if he violated his probation.
In short order, the charges continued to pile up.
While in custody of the state, Skerritt escaped from youth detention officials during a scheduled visit to a Boston dentist’s office. A review of the incident found that Skerritt might’ve had a handcuff key.
After the escape, the judge in the Walgreens case revoked his probation and ordered him to spend 2½ years in an adult jail, records show.
Another time, he pleaded guilty to assaulting a Nashua Street Jail correction officer after the man had cut short a visit.
Soon, Skerritt was eyed in more serious crimes.
As early as 2010, court records show, Skerritt was a named a person of interest in a homicide, a case that never amounted to charges against him. That same year, he was arrested on the first of what would be multiple firearms charges. During a confrontation with officers who’d stopped a Jaguar registered in his name, a loaded black handgun fell on the floor of the vehicle where Skerritt had been sitting, Boston police said.
”I’m going away for a long time,” Skerritt allegedly told one of the officers who arrested him, according to court records. “I know I should have stayed in tonight.”
Skerritt later pleaded guilty to two firearms charges, court records show, and was sentenced to five years in prison.
He’d been out just two months when, in January 2014, police discovered Julien Printemps ’s body, riddled with bullets, laid out in the parking lot of a commercial strip off Dorchester Avenue.
According to authorities, Printemps had been leaving the parking lot of a convenience store around 10 one night when another vehicle pulled into the parking lot. The other driver exited his vehicle and words were exchanged. Then the other driver pulled a semi-automatic pistol and began shooting.
As Printemps attempted to pull away, authorities said, the shooter pursued him, firing more shots before returning to his vehicle and fleeing the scene.
Skerritt was charged more than a year later with pulling the trigger.
Following a five-day trial, jurors were unmoved by the prosecution’s case. In court papers, a defense attorney said prosecutors had only one witness who identified Skerritt at the shooting scene and lacked physical evidence linking him to the crime.
Skerritt was acquitted in the killing in November 2017.
James Greenberg, a defense lawyer for Skerritt in the homicide trial, told the Globe the state’s lack of evidence in the case paved the way for his client’s acquittal.
“I would say [he was] rightfully acquitted by the jury,” Greenberg added.
Skerritt’s letters from a state prison in Shirley were penned in small, neat handwriting.
The prison correspondence, which was filed in court, is littered with bravado. He asks women to send illicit photos, boasts of his ability to beat cases, and details fights with others — bragging, in one instance, that he tried to “open” another inmate’s face with a razor.
“No matter what they hit me with I won’t break,” he wrote in one letter. “I won’t even flinch.”
Writing to an acquaintance, he claimed the murder charge he was facing relied on testimony from a former girlfriend. “If she don’t make it to testify that would [be] even better,” he wrote in September 2015.
Other times, he spoke of regret.
“I [yearned] for acceptance and did whatever I had to do to gain it,” he wrote in a 2014 letter. “I used to believe a reputation was everything but once I’m in this cold cell all alone I don’t see or hear from nobody but the family that warned me time and time again.
“I was hardheaded,” he continued. “I still kind of am because who I tried hard to be I eventually became and I didn’t know how difficult it would be trying to unchange that.”
Those moments of self-reflection, however, appear fleeting.
On Feb. 5, 2020, police responding to a report of shots fired discovered Skerritt perched on the back steps of a property in Pawtucket, R.I., holding his chest and stomach. Gunpowder still hung in the air.
Skerritt had been shot twice in the chest. While searching a recycling bin next to where Skerritt sat, officers recovered two bags of suspected cocaine as well as an inoperable handgun.
Police charged Skerritt with a drug offense, and he was released on bond. The charges are still pending.
Just a few days after Thanksgiving in 2021, State Police Trooper Brian Kilfoyle noticed a Chevy Equinox with highly tinted windows driving on a commercial strip in Fall River. Skerritt sat behind the wheel.
A search of the vehicle turned up more than 40 grams of crack cocaine, police said.
Given his extensive criminal history, and the amount of drugs seized, Skerritt faced a lengthy potential prison sentence.
Before the case advanced to trial, however, prosecutors were forced to drop the charges; State Police had lacked probable cause to stop the vehicle because Massachusetts’ window tint rules don’t apply to vehicles registered out of state. The rental vehicle Skerritt was driving was registered in Florida.
Again, Skerritt went free.
And it wasn’t long after, police say, that he found himself on a Mattapan street corner on a Sunday morning.
In the wake of the Tyler Lawrence shooting, the FBI arrested Skerritt on unrelated drug charges, part of a federal probe that appears to have been unfolding simultaneously.
Agents took him into custody on Feb. 5 for allegedly selling about 55 grams of fentanyl to a cooperating witness four days earlier, according to an affidavit filed in US District Court. The affidavit described Skerritt as an associate of a Boston street gang.
A day after his arrest, Boston police and Hayden’s office announced Skerritt would also be prosecuted in Lawrence’s killing . A prosecutor later said video footage and eyewitness accounts link Skerritt to the fatal shooting.
In a recent court appearance in the drug case, Skerritt seemed unbothered; sitting at the defense table awaiting the start of the hearing, he smiled and laughed — his smile growing after a young, pregnant woman made her way into the courtroom and took a seat in the gallery. He mouthed, “I love you” and blew kisses to her.
In a state court arraignment Tuesday, Skerritt pleaded not guilty to killing Lawrence.
The murder has touched off a mix of soul-searching, shame, and despair in a city that has named playgrounds, parks, and fields for its youngest victims of gun violence, including Darlene Tiffany Moore, 10-year-old Trina Persad, and 9-year-old Jermaine “Manny” Goffigan.
After the Lawrence killing, public officials have vowed to do more to protect the city’s children from violence.
“We will go above and beyond in every way possible to make sure the youngest citizens of the city are safe,” Boston Police Commissioner Michael Cox told reporters last month.
As Boston Mayor Michelle Wu put it, “We have a lot of work to do.”