NATICK — They began by apologizing.
Joseph Donovan and Frederick Christian, both 17 when they committed crimes that led to killings, began their pleas for freedom with expressions of deep remorse for actions more than two decades old.
“I was such a stupid kid,” Donovan, now 38, told the Massachusetts Parole Board Thursday about punching MIT student Ynvge Raustein in 1992, before Donovan’s codefendant stabbed Raustein to death.
“I’m very ashamed,” said Frederick Christian, 37, who watched in 1994 as a friend fatally shot two men, Kepler Desir and Manuel Araujo, and left a third, Araujo’s brother, Carlos, for dead.
Sentenced to life in prison without parole for the crimes they committed as juveniles, neither man was supposed to have a chance to make such a case. But a Supreme Judicial Court decision in December made it unconstitutional to sentence to life without parole defendants who were under 18 years old when they committed their crimes, even if those crimes were first-degree murder.
Donovan and Christian are among 65 Massachusetts people affected by the decision and they were the first two inmates to go before the board. Their hearings, conducted separately, drew dozens of people, including supporters and opponents, anxious to see how the board will handle their cases.
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The six Parole Board members who presided over the hearing in the two-story office building across from the Natick Mall will have to meet and deliberate both cases before taking a vote, a process that could take several months. Their primary goal will be to determine whether either man still poses a threat to others and if they were rehabilitated while incarcerated.
Donovan, who appeared first, faced some of the toughest questions from the board, which expressed grave concerns with his record as an inmate.
He spent seven years in solitary confinement in a special program for offenders after he punched a correctional officer several times. The first six years of his incarceration were marked by several violent incidents, most of them assaults on other inmates.
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Donovan acknowledged his past and told the board he was a frightened, angry man who behaved without thinking and fought to keep other inmates at bay.
“A lot of people are impulsive, but they don’t punch people,’’ Parole Board chairman Joshua Wall told Donovan at one point. “This is quite a violent record.’’
Donovan said that his time in solitary helped calm him down. It was there he said he learned to stop blaming others for the problems in his life.
“I didn’t emphathize,” he said. “I didn’t put myself in other people’s shoes.”
Donovan said he began drawing, reading more, immersing himself in the works of Plato and Albert Einstein, and taking courses to become a paralegal.
In a rare light moment during the proceedings, board member Charlene Bonner asked Donovan if it was true he read “Relativity: The Special and General Theory.”
“Haven’t you been punished enough?” she asked.
Donovan laughed.
“I’m a big Einstein fan,” he said. “The guy is a genius.”
Donovan’s record is free of offenses after 2009. Still, board members said they were concerned that he had not participated in more self-improvement programs in prison and dismissed his argument that he was wait-listed, arguing that other inmates in his position have successfully advocated to be enrolled.
“There are a lot of people at the [Department of Correction] who did not choose the path you chose,” Wall said.
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By contrast, Christian enrolled in several antiviolence programs, worked consistently, became deeply involved in the Muslim faith, and avoided a significant disciplinary record. None of his infractions during the 20 years following his conviction were for violent offenses.
Christian said he joined self-help programs to avoid trouble and because he saw the positive effect it had on others. He said he held out hope that he could still be released despite his sentence.
“That was one of the reasons I tried to better myself,” he said.
Still, when it came time for the public hearing portion of the proceeding, three witnesses came forward to argue against his release: Plymouth District Attorney Timothy J. Cruz; Carlos Araujo, and Desir’s girlfriend.
Cruz forcefully urged the board not to grant parole and to see Chrisitian as a calculating criminal who knew full well the plan to kill the two victims in his case.
“A convicted, cold-blooded killer, Christian shows his remorse only when he has his freedom to gain,” he said.
Araujo, now 38, said he was distraught that the only reason Christian had a right to a hearing is because the crime happened a few months before his 18th birthday.
“There is no way that you intelligent people can let him come out,” Araujo said.
Raustein’s family has supported Donovan’s release.
Middlesex Assistant District Attorney John McEvoy, who prosecuted Donovan, stopped short of arguing against parole and said that he had “serious reservations” about giving freedom to a man who had so much trouble in prison and whose version of what happened the night of the crime differs from that of other witnesses. He said that if the Parole Board decides to release him, it should be done through a more gradual process.
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“It seems everyone agrees that Mr. Donovan should not be released immediately to the streets,” McEvoy said. “I don’t see that he should come out cold turkey.”
Maria Cramer can be reached at mcramer@globe.com. Follow her on Twitter @globemcramer.