WARREN, Maine – William Flynn depicts himself as a do-gooder, a member of the Jaycees who has a wife and teenage stepdaughter and likes to play softball.
At least that's how he'd like to be seen by a judge, who's considering freeing Flynn early from the 28 years-to-life prison term he got for killing his lover's husband as a teenager in the notorious Pamela Smart murder case.
Since going to prison nearly two decades ago, Flynn has earned a high school equivalency degree and an electrician's helper license, gotten married and raised money for charity. He says in court documents that he has transformed himself into a thoughtful and caring adult, intent on helping others.
Flynn, 33, was 16 and having an affair with Smart when he shot and killed her husband in New Hampshire in 1990.
In his petition to the judge, Flynn writes in a six-page handwritten letter that the guilt and shame he feels is like wearing a "huge weight strapped permanently across your shoulders."
Prosecutors oppose Flynn's request, as does the family of the victim, Gregory Smart. A hearing is set for Friday in Rockingham Superior Court in Brentwood, N.H.
Flynn's court file contains more than three dozen letters of support from prison employees, friends and others who know him. Another nine letters come from people who say they would hire Flynn once he is released.
In the motion, Flynn asks for a sentence reduction because he has now spent more than half his life in prison.
"He has used those years to develop from a boy into a man of great character, fully rehabilitated and ready to contribute to society upon his release from incarceration," says his lawyer, Cathy Green of Manchester, N.H.
That's quite a contrast from the angry and withdrawn teenager who, as a high school sophomore, shot Gregory Smart in the back of the head as Smart begged for mercy from his knees. The murder scheme was concocted by Pamela Smart, who is serving a life sentence in a New York prison for her role.
Assistant Attorney General Kirsten Wilson said reducing his term would undermine the sentencing goals of punishment, rehabilitation and deterrence.
"As he has yet to serve the minimum of his sentence, he has not been appropriately punished for his crime," she wrote.
Eighteen years ago, Flynn and his high school buddies were smitten with Pamela Smart, a blonde 23-year-old who worked at their high school in Hampton, N.H. They became lovers, he testified, and she enlisted him to kill her husband of less than a year.
On May 1, 1990, Flynn and a friend entered the Smarts' condominium and grabbed Gregory Smart. The friend held a knife to Smart's throat, and Flynn — after asking God for forgiveness — fired a .38-caliber revolver. Two other teenage friends were in a getaway car.
In exchange for testifying against Pamela Smart, Flynn pleaded guilty to second-degree murder.
Her lawyers argued that Flynn wanted Gregory Smart out of the way so he could continue the affair. Prosecutors said Smart wanted her husband killed so she wouldn't lose her condo, furniture and dog in a divorce.
Flynn, who did not respond to requests to be interviewed, wrote to the judge that he's not worthy of the Smart family's forgiveness, but wants them to know that "the word sorry fails to express the depth of what I feel."
Flynn is so trusted in prison that he has been given work on prison security and camera systems, the court file shows. He is a member of the prison Jaycees, the NAACP and the Kairos Christian organization.
He is director of the Long Timers Group and chairman of the Peer Education Group. He plays guitar, soccer and softball, and has helped raise money for the Toys for Tots program and Salvation Army. He also helped build a children's playhouse for a family that moved to Maine after Hurricane Katrina.
Flynn has also gotten married. In a letter to the court, his wife, Kelly Flynn, says she owns a house where she lives with her teenage daughter. She said her husband has turned himself around in prison through self-examination and hard work.
"Bill has become a man who is worthy of respect, despite his past record," writes Kelly Flynn, who declined to be interviewed.
Flynn may have a tough time persuading Justice Kenneth McHugh that his sentence should be reduced.
It could be argued that Flynn's sentence was reduced at the time of sentencing through a plea bargain, said Charles Putnam, co-director of the Justiceworks research institute at University of New Hampshire and a former homicide prosecutor. At the time, his sentence was cut from 40 to 28 years because of his youth and other factors.
And it will be hard to overlook the image of Flynn pulling the trigger.
"From my perspective," Putnam said, "holding another human being who is begging to be spared, and pulling the trigger on that human being and voluntarily and purposely ending the life of that human being is a momentous act."