Stepping outside his sprawling Maine home in a casual checked shirt and blue jeans, William Flynn looked every inch the respectable New England businessman as he climbed into a Porsche and headed to a networking event.
Yet at just 16 years old, Flynn was once at the center of one of America’s most notorious murder-for-hire cases.
He served decades in jail after admitting to killing Gregg Smart, the husband of his older lover Pamela Smart, who prosecutors said seduced and manipulated him into the murder.
Exclusive Daily Mail photos show the now 52-year-old Flynn sporting salt-and-pepper hair and a neat goatee. This is the first time he has been seen since issuing a sobbing courtroom apology for Gregg’s murder in 2008.
The sighting also comes just weeks after his bleach blonde former flame, now 58, appeared for a virtual court hearing in New Hampshire as part of her latest legal bid to have her conviction overturned.
Smart is seeking a new trial, arguing prosecutors misled the jury by giving them inaccurate transcripts of secretly recorded conversations she had following her husband’s killing.
Smart was a 22-year-old high school district media coordinator when she embarked on an illicit affair with 15-year-old ‘Billy’ Flynn after meeting him on a self-awareness course she mentored at Winnicunnet High School, Hampton, New Hampshire.
Prosecutors said she told him the only way they could be together was if he killed her husband.
William Flynn, now 52, has built a new life for himself in suburban Maine, 36 years after the murder of Gregg Smart, exclusive Daily Mail photos show
Flynn, pictured in 1991, was just 16 when he carried out the murder, at the behest of his older lover Pamela Smart, who was married to the victim
Flynn and his three teenage pals carried out what prosecutors said was Smart’s ‘black widow’ style plan to kill her 24-year-old husband in a staged burglary at their condo in Derry, New Hampshire.
On May 1, 1990, Flynn and pal Patrick ‘Pete’ Randall went inside the condo and forced Gregg, an insurance salesman, to his knees.
Randall held a knife to Gregg’s throat before Flynn shot him in the head. Their friends Vance Lattime and Raymond Fowler waited outside in the getaway car.
As part of a plea deal, Flynn tearfully testified against Smart in a highly sensationalized trial that was the first to air in full on live TV, captivating the nation.
The trial would later inspire books and movies, including the Joyce Maynard novel ‘To Die For’, which was made into a 1995 film of the same name starring Nicole Kidman and Joaquin Phoenix.
Flynn and Randall pleaded guilty to second-degree murder and were given a 28-to-life stretch in prison. They were both released in 2015 on lifetime parole after serving 25 years.
Lattime and Fowler served shorter sentences and have also been released.
Smart, who continues to deny any knowledge of the plot, was convicted as an accomplice to first-degree murder and other crimes and sentenced to life without parole.
Smart (left), 56, who is serving life in prison for the murder-for-hire plot on husband Greg Smart (right) in 1990, has filed to appeal her conviction multiple times and most recently in 2024, launched a bid for a sentence reduction
Smart, pictured during the 1991 trial, is seeking a new trial, claiming prosecutors misled the jury
Since his release, Flynn has quietly built a new life with Kelly, 59, his wife of two decades, in the post-card perfect midcoastal town of Newcastle, Maine, some 35 miles north-west of the state capital, Augusta.
Flynn wed Kelly, a divorcee with a daughter, in 2005 while behind bars after she began writing to him.
Despite his troubling past, he appears to have firmly embedded himself in the local community.
The couple live in an elegant Cape Cod-style home, which is set on 3.4 acres and estimated to be worth almost $565,000, more than twice what Kelly paid for it in 2006.
Flynn, who earned his GED while in jail and holds a journeyman’s electrician’s license, appears in business records as running his own electrical contracting firm, Newcastle Electric, since 2018, with the firm reporting $352,000 of annual sales in June.
The couple’s home boasts a double garage with ample space to accommodate Flynn’s workshop and his apparent fleet of vehicles which include, a black pickup truck, a 2022 Kawasaki Jet Ski, and a WolverineMax2 1000 ATV, licensing records show.
Flynn had few words for Smart’s latest bid for freedom, save for the wry observation: ‘That seems to happen every so often.’
Asked about the trial, his conviction and how he has seemingly turned his life around, Flynn maintained his decades-long silence on the matter, adding: ‘I don’t talk about that at all.
Today, Flynn, sporting salt-and-pepper hair and a neat goatee, looks like a typical suburban businessman as he lives a comfortable life in Newcastle, Maine
These days, Flynn runs his own electrical contracting firm and has been pictured mingling at business networking events with wife Kelly (pictured together in a social media photo) a licensed insurance agent
‘I’m sorry you came all this way, but it’s just not a thing I talk about,’ he added, before shutting the door.
Flynn has made scant public comment on the case since he issued a sobbing courtroom apology to the Smart family when he successfully applied in 2008 to have his sentence reduced by three years.
‘I want you to know that I’m very sorry,’ he said at the time, insisting he took ‘full responsibility’ for his crimes before blaming feelings of teenage insecurity and his family for abandoning him.
He also blamed Smart for exploiting his vulnerability when she threatened to end their illicit affair, admitting: ‘I would have killed for her and she knew that.
‘I know none of this excuses what I did. Every day I think about what I’ve done to you and the people I hurt and I’m terribly and deeply ashamed of myself for being so weak.’
Even after being granted parole on his 41st birthday in March 2015, Flynn said he would always be haunted by the guilt he felt at the pain he had caused the Smart family.
But Jillian Smart, Gregg’s cousin, said the family’s ire is now mostly reserved for Smart, who has yet to admit her role in masterminding Gregg’s murder.
‘Myself and [Gregg’s] cousins stand behind the court’s decision and are against any appeal,’ Jillian, 50, told the Daily Mail.
In 2008, 16 years into his sentence, Flynn issued a sobbing courtroom apology for Gregg’s murder
Patrick ‘Pete’ Randall, an accomplice in the murder, was sentenced to 25 years and was released in 2015. Randall held a knife to Gregg’s throat before Flynn shot him in the head
The infamous trial inspired books and movies, including 1995 film To Die For, starring Nicole Kidman
‘She [Smart] should remain in jail as she’s been sentenced, for the remainder of the rest of her life, because my cousin was never able to live his life because of her.
‘She won’t even admit her guilt. She’s not even remorseful for what she’s done.’
As for Flynn and the other accomplices, Jillian believes they ‘admitted their guilt’ and says: ‘I forgive them to a point, because I feel like they were very young and they were manipulated.
‘If it wasn’t for Pam, this wouldn’t have happened. They were just kids. They were used as a pawn to carry out what she couldn’t just do the right way.’
She said every time Smart lodges a legal challenge to her sentence or conviction, it brings up Gregg’s murder ‘like it was yesterday, and we have to live through it over and over again’.
Flynn’s new life is worlds away from the current fate of his former paramour.
Smart has been incarcerated for more than 35 years and is serving time at the Bedford Hills Correctional Facility in Westchester County, New York.
There, she has earned a doctorate, three master’s degrees, helped fellow inmates and been ordained as a minister, according to her longtime media spokesperson, Eleanor Pam.
Smart (pictured in mug shot) was a 22-year-old high school media coordinator when she began an affair with a 15-year-old boy, Billy Flynn, in Derry, New Hampshire
Smart, now 58 and pictured in a 2026 mugshot, recently appeared for a virtual court hearing in New Hampshire as part of her latest legal bid to have her conviction overturned
But Smart is still furious that Flynn and the other boys who perpetrated her husband’s murder are free while she remains behind bars.
‘She feels fury, absolute fury, because she is serving their sentence. They did this on her back,’ Pam told the Daily Mail.
Pam claims Flynn, Randall and Lattime cooked up their plot to blame Smart when they were housed together in prison, in a bid to avoid a harsher sentence.
‘They were given a plea bargain if they testified against her, so they got together and they all said the same story.
‘So, you have to wonder whether their testimony was a true testimony.’
According to Pam, the ‘guilt’ Smart feels today is about her affair with Flynn, her ‘bad judgment’, and her failure to pick up the deadly chain of events it would set in motion.
‘She knows that her husband would be alive if it weren’t for her own bad decisions,’ she added.
But the woman dubbed the ‘Ice Princess’ by media at the time continues to dodge responsibility for orchestrating Gregg’s murder.
‘She absolutely denies that she had anything to do – directly or indirectly – with the murder of her husband, that she knew about it, or that she even wanted it.’
Pam insisted Smart has been a model inmate and shown true remorse over her husband’s death.
Whether Smart ever does get granted parole, will be up to a judge to decide.
