William “Billy” Flynn, the teenage trigger man in the notorious 1990 New Hampshire murder that made Pamela Smart a household name, has asked Maine prison officials for permission to make 48-hour visits to his wife’s home, the Kennebec Journal has learned.

Flynn was 16 years old and having an affair with Smart, a 22-year-old employee at his school, when he shot and killed Gregg Smart at the couple’s Derry, N.H., home on May 1, 1990.

The March 1991 trial, complete with lurid details of a love triangle, was one of the most sensational in New Hampshire history and the first to be nationally televised live in its entirety. It provided fodder for tabloids, attracted international media attention and inspired the Joyce Maynard book “To Die For,” the basis of the 1995 movie starring Nicole Kidman. Currently, the case is the topic of an HBO documentary, “Captivated: The Trials of Pamela Smart,” which argues that Smart was unfairly convicted because of intense media coverage.

Flynn, 40, has been in Maine’s prison system since 1993, after he was sentenced to between 28 years and life in prison. He was described by corrections officers and his attorney as a model prisoner before his sentence was reduced in 2008. He’s eligible for parole in June 2015.

Now Flynn has made a request to the Maine Department of Corrections to be furloughed from Bolduc Correctional Facility in Warren, where he has been held since 2013, officials said. He is seeking visits to nearby Newcastle, where his wife lives.


In July, The Associated Press reported that Flynn was allowed into a work release program in Warren. In those programs, prisoners can leave prison for work but must return when done. The corrections department investigates and must approve furlough requests.

Lincoln County Sheriff Todd Brackett and Jeffery Strelzin, an assistant New Hampshire attorney general, said their offices have been notified of the request. Corrections spokesman Scott Fish wouldn’t confirm or deny Flynn’s furlough request on Wednesday, saying state law prohibits confirming furloughs unless they have been approved. That means Flynn’s furlough hasn’t yet been authorized.

Kelly Flynn, the prisoner’s wife since 2006, and Flynn’s attorney from Manchester, N.H., Cathy Green, didn’t return calls seeking comment on the request. Neither did Rick Smart, Gregg Smart’s brother.

However, Brackett said his notification indicated that Flynn would spend his furlough time in Newcastle. Town records show Kelly Flynn, who met and married her husband while he was in prison, has a home on Academy Hill, near Lincoln Academy, which is private but serves as the local high school and a boarding school.

Maine’s furlough policy typically allows some prisoners with clean disciplinary records to be released intermittently toward their sentences’ end for 48-hour periods over three days to approved addresses where they must remain and be reachable by phone. During furloughs prisoners can’t drive and must return to prison at a designated time. Fish couldn’t provide annual statistics on prisoner furloughs that are requested and approved.

Furloughs are a good way to prepare prisoners for the outside world in a controlled way after years in an environment where they’re told how to live, said Scott Riiska, a case manager who works at the Cumberland County jail in Portland for the Maine Department of Health and Human Services and a lecturer in criminology at the University of Southern Maine.

“Just to go home for the weekend and have control over what time you go to bed is huge,” he said.

The prospect of Flynn’s temporary release doesn’t worry the county sheriff, who said he can’t recall an issue with a furloughed prisoner in his time in law enforcement, calling it part of the process of reintegrating ex-convicts.

“These folks are really trying to make it work here, and this is how the justice system works,” Brackett said.


Flynn was convicted of second-degree murder, and three friends were convicted as accomplices. According to court records, Flynn shot Gregg Smart once in the head as Pete Randall held a knife to the victim’s throat. Vince Lattime and Ray Fowler waited in the car. Flynn was sent to Maine to serve his sentence; separating convicts is common in cases with many defendants.

New Hampshire court records show that Flynn has done well in Maine’s prison system. After becoming licensed as an electrician’s helper in 2002, he worked as an employee of the Maine State Prison’s electrical department, getting excellent reviews. State records show that he passed an exam in July to qualify for a license as a journeyman electrician.

He has also worked in prisoner support groups and on a Toys for Tots program in the Rockland area. One of several correctional officers to praise him in 2008 said that Flynn had “grown from a confused teenager who made an egregious mistake into a responsible, caring individual that would be a positive addition to any community, whether inside or outside a fence.”

Pamela Smart wasn’t at the scene of the 1990 murder, but she was held responsible for most of it. Flynn testified that she recruited him and his friends to kill her husband, saying she didn’t want to lose possessions in a divorce. Flynn, who was 15 when the relationship started, said she threatened to end their relationship if he didn’t kill her husband.

Smart has maintained her innocence, blaming Flynn for the murder. She got a life sentence without possibility of parole for conspiring to kill her husband and other charges.

Flynn, Randall, Fowler and Lattime are either on work release or out of prison now.

In a written statement to the Kennebec Journal, Eleanor Pam, Smart’s counselor and spokeswoman, said Flynn’s “posturing has paid off” as Smart remains behind bars.

“Her future is an unjust and obscene sentence which stretches endlessly into perpetuity,” Pam wrote. “Where is the balance? Where is the fairness?”

Michael Shepherd can be contacted at 370-7652 or at:

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