BRENTWOOD — Triggerman William Flynn apologized to members of the family of the man he killed nearly 18 years ago for his role in the coldblooded and calculated murder of Gregory Smart.

He addressed the family during a hearing Friday for the request of a sentence reduction. Tears were shed and apologies were accepted, and although the hearing lasted nearly two hours, ultimately Flynn, 33, will have to wait a little longer for a Superior Court judge to consider his request for release from a Maine state prison.

Flynn faced members of the Smart family as he spoke and said the shame, guilt and remorse he has felt ever since that fateful day in May of 1990 is insurmountable.

Flynn, just 16 at the time, was having an affair with Smart's wife Pam, then a 22-year-old Winnacunnet High School media coordinator.

"I know that I can never make amends for the pain and I promise you I will carry this guilt and remorse with me every day for the rest of my life," said Flynn. "It has never diminished and I hope it never will."

Numerous members of the Smart family packed the Rockingham County courtroom to hear arguments regarding Flynn's request to be freed from prison. Having served 18 years of a 28 years to life sentence, Flynn is petitioning to be released early citing good behavior and active involvement within the prison community as well as several charities.

Although he isn't eligible for parole for another 10 years, Flynn is asking to be released now that he has spent more than half his life behind bars.

"I desperately want you to know I'm not that weak person anymore," he said, still addressing the Smart family.

Attorney Paul Maggiotto, who originally prosecuted Flynn, testified in front of Judge Kenneth McHugh and said that it was his belief that Flynn was acting at the behest of Pamela Smart when he fired a single round from a .38-caliber revolver into the back of Gregg Smart's head.

"It was our belief and position, (that) but for Pam Smart, Bill Flynn wouldn't have been in that apartment," Maggiotto testified. "Clearly, Bill was acting at behest of Pam Smart."

Maggiotto also said he was impressed with Flynn's disposition as it showed sincerity and a willingness to make amends with his wrongdoing. Flynn originally pleaded guilty to second-degree murder and Maggiotto said Flynn not only cooperated with prosecutors but was a key witness against Smart in her trial.

"I think Bill has nurtured the seeds I saw in him when he was cooperating with us and those seeds have grown," Maggiotto said. "He's grown into what I characterize as an exemplary individual."

The state, along with Gregory Smart's family, opposed granting Flynn a sentence reduction.

Representing the state, Senior Assistant Attorney General Susan Morrell argued Flynn's request was not only unjust but also unwarranted. Morrell said Flynn had already been rewarded with a lesser sentence for his cooperation in the successful prosecution of Pamela Smart and that his age at the time of the murder had already been taken into account with the sentence he is currently serving.

William Smart, Gregg's father, accepted Flynn's apology in court, but said he didn't believe Flynn should be released just yet.

"I'm going to make you a little promise," said William Smart. "When you turn 40, if you're still in jail, I would like to hear from you again. At that point I think I would agree to let you out of jail."

Gregg's brother, Dean Smart, also addressed the court and promised that while it may be Flynn's wish not to be remembered for the infamous murder, he will do everything he can to ensure that Flynn never forgets about the life that he took.

Dean Smart also questioned why Flynn wanted a reduction given that he had already reached a negotiated plea deal in the original trial.

"If you were a man of honor you wouldn't go back on your word," said Dean Smart of Flynn's request.

McHugh addressed the court before adjourning and said he would have to take some time to consider all of the evidence presented before ruling.

"There are never any winners in a case like this," said McHugh. "Everyone loses."

Morrell said she anticipates a decision from McHugh in a matter of weeks.