ON A TUESDAY night, 1 May 1990, 16-year-old Bill Flynn and and his friend Pete Randall walked into local insurance salesman Gregory Smart’s condominium in the town of Derry, New Hampshire.
They lay in wait for Gregg to come home, ambushed him, beat him up, and ordered him on his knees.
Randall, a tough local kid, held a knife to the 24-year-old’s throat, as he pleaded for mercy.
Then, in Bill’s words:
I cocked the hammer back, and I pointed the gun at his head. I said “God forgive me.” Then I pulled the trigger.
25 years later, at midnight on Wednesday, 41-year-old Bill Flynn walked free from Bolduc Correctional Facility in the state of Maine.
Pamela Smart, the wife of the victim, and Bill’s school instructor and lover, wasn’t in the room when her husband died. But she will never leave prison alive.
This is the story of the original “fatal affair” between teacher and student.
It was a sensational, twisting and turning murder that launched a thousand true crime novels and made-for-TV movies and, years before OJ Simpson, the first ever televised “trial of the century.”
‘All the guys in school were attracted to her, and of everybody, she liked me’
The Smart home had been ransacked, and some property stolen, so investigators worked off the assumption that a burglary or drug deal had been disrupted or gone wrong.
In the aftermath, however, Pamela’s demeanour raised eyebrows. As recounted in the HBO documentary “Captivated,” she appeared just a little bit too keen to speak to the media.
On one occasion she called a reporter out of the blue, and invited them to her home for an interview. On another, she suggested imagery that would make a TV segment “more poignant.”
At the same time, rumours were swirling in the local communities of Derry, Seabrook and Hampton, where Pamela worked, on the grounds of Winnacunnet High School.
She had been spending a lot of time after school hours with 15-year-old Bill Flynn, supervising him and a small group of students, as they produced an orange juice ad for a national schools contest.
Flynn had a big crush on Smart, a former cheerleader, who was good-looking, cheerful, friendly, and shared his love for metal music.
He later said:
She was attractive. All the guys in school were attracted to her. She was intelligent, exciting to be around. And of everybody, she liked me.
They “became sexually involved” in February/March 1990, according to court records.
This is around the point that accounts diverge. Smart says she grew “uncomfortable” with the affair, and ended the relationship two months in.
Flynn says she told him they could stay together, but only if he killed her husband.
“We have some good news and some bad news”
That spring, Bill and his friends Vance “JR” Lattime, Patrick “Pete” Randall, and Raymond Fowler, began planning the murder.
On 1 May, Lattime was the driver, and he and Fowler waited in the getaway car while Randall and Flynn entered the home through the basement door, which was left open, and killed Smart.
As police began to link the killers to the victim, through Pamela’s connection with the school that all four attended, her affair with Flynn became known, and she suddenly withdrew from the public eye, refusing to speak to the media.
In the weeks after the murder, someone let the cat out of the bag, and Ralph Welch, a local teen, told Vance Lattime’s parents about the whole thing.
The gun used to kill Gregg Smart belonged to Lattime’s father, who immediately took it to police, where ballistics tests confirmed its role in the murder.
The next day, Flynn, Randall and Lattime were arrested, and the conspiracy of silence began to crumble.
Cecelia Pierce, a 15-year-old student who considered Pamela her friend and mentor, had been working on the orange juice ad, and witnessed their affair first-hand.
She claimed Smart had talked constantly about planning her husband’s murder, and was taken in for questioning by police.
Open to prosecution for not reporting the plan before it was carried out, Pierce agreed to wear a wire.
The result was a damning audio recording of Smart appearing to ask Pierce to lie to police, to prevent everyone involved “ending up in the slammer for life.”
On 1 August, Detective Daniel Pelletier arrived at Smart’s office on the grounds of Winnacunnet High School.
We have some good news and some bad news.
The good news is, we finally solved the murder of your husband. The bad news is, you’re under arrest.
‘We interrupt this broadcast…’
Pamela Smart was accused of orchestrating the entire murder plot – threatening to end her sexual relationship with Flynn, and offering to pay the others $500 each, according to court records.
She was charged with being an accomplice to first degree murder, conspiracy to murder, and witness tampering (for asking Cecelia Pierce to lie).
The three boys pleaded guilty to second-degree murder, in return for testifying against Smart as the mastermind.
Before her trial even began, in March 1991, the media circus was in full flow. TV coverage was wall-to-wall, first in the New Hampshire area, driven by local channel WMUR, then in the Boston region, and soon, it was national news.
Smart was quickly and consistently depicted as the “Ice Queen” and “Black Widow” – ruthlessly using sex to manipulate an impressionable teenage boy to do her bidding, help her avoid an expensive divorce, and cash in on her husband’s life insurance policy.
Normal programming on local TV was interrupted to bring updates from the case.
America had never seen anything quite like it. It was the first court case televised from beginning to end, and until OJ Simpson at least, it was the “Trial of the Century.”
It went on to inspire the best-selling novel “To Die For”, which was made into a movie starring Nicole Kidman and Jaoquin Phoenix as Pam and Bill, as well as countless “true crime” movies and books.
Flynn, Lattime and Randall all testified against Pamela, with Flynn’s tearful confessions proving particularly powerful.
Her former intern, Cecelia Pierce, also spoke against her, and when their taped conversation was played in court, it seemed inevitable the jury would conclude she had orchestrated her husband’s killing.
After two weeks, on 22 March, she was convicted, and sentenced to life in prison without the possibility of parole.
Flynn, Lattime and Randall – who were charged as adults – were all handed life sentences for second-degree murder, with parole due after 40 years, but with 12 years each suspended, giving them minimum sentences of 28 years.
Raymond Fowler, who waited in the getaway car, got 30 years for conspiracy to murder, with parole after 15 years.
Pamela Smart’s Defence
For the last 25 years, Smart has consistently pleaded her innocence, and appealed for a reduction in her sentence.
She has given several major, primetime TV interviews over the years, including an appearance on Oprah in 2010.
Just last month, she told Inside Edition she’d rather have received the death penalty, than face the prospect of dying in prison.
Her defence is complicated and detailed, but here’s a short run-down of arguments Smart and her defenders have claimed undermine the prevailing narrative against her.
The media circus
She argued strongly that an “avalanche” of pre-trial publicity made it impossible for her to get a fair trial, but the court disagreed, noting that she herself had stoked the flames by enthusiastically doing interview after interview with the local press.
Her former lawyer, Albert Johnson, told HBO:
Everybody involved in the Pamela Smart trial was caught up in a black hole of media attention.
At one point, it was reported that Judge Douglas Gray had said offhand during the trial that he hoped Clint Eastwood would play him when the movie came out.
Her co-conspirators
Plea bargains are a perennial source of scepticism when it comes to court testimony.
Acknowledged co-conspirators are, as a rule, separated and prevented from communicating with each other, to avoid exactly this possible outcome.
The tapes
This was the most damning piece of evidence in the trial, and the hardest to refute. It doesn’t depend on hearsay, but involves words spoken by Pamela Smart herself.
She was recorded encouraging Pierce to lie to police, and saying “nothing was going wrong” until Ralph Welch was told about the murder.
However, Smart has argued:
The audio is of an extremely low quality, something that even prosecutors have acknowledged.
Over the last 25 years, Smart has brought numerous lawsuits and appeals before local, state and federal courts, almost entirely without success.
She remains behind bars, at the maximum security women’s prison in Bedford Hills, New York, and without an executive order from the Governor, will stay there for the rest of her life.
‘The first thing people learn about me is the worst thing I’ve ever done’
Bill Flynn’s last quarter of a century has been drastically different from his former lover’s.
By all accounts, he has served his sentence quietly, without incident or controversy, and been a positive influence on his fellow inmates.
He applied for early release in 2007, and was denied, but had three years shaved off his minimum sentence.
Flynn became a trained electrician, got a college degree, and even got married, and has stepchildren. In 2014, he was moved to a minimum security prison in Maine, and began working in the community on day release.
On 12 March, his 41st birthday, he was finally granted parole, joining JR Lattime and Raymond Fowler, who have both been out since 2005.
Flynn, as he has since 1990, expressed remorse for pulling the trigger, and apologised once again to the family of Gregg Smart.
Looking ahead to his new life as a free man, he noted poignantly:
These days, the first thing that people do is Google you. So the first thing people learn about me is the worst thing I’ve ever done…But that’s a situation I deserve.
On Wednesday night, at the same time as Pete Randall, he walked free. He’ll be on parole for the next 10 years.
“I hope he does something great with the rest of his life”
The family of Gregg Smart have gone on their own journey over the last 25 years.
They have never shown any conciliation towards Pamela, saying her claims of innocence, frequent TV interviews, and repeated appeals force them to relive the trauma of Gregg’s death, over and over again.
Their position towards Bill Flynn and the three other boys, however, has evolved in a remarkable way.
Here’s Gregg’s father Bill and younger brother Dean in 2008, confronting a sobbing Flynn, as he applied for a reduction in his sentence.
I got an answer for you, Flynn. And it’s the same answer that you, William Flynn, gave my brother Gregory Smart 17 years ago, as he begged for mercy.
And that answer is – Bang! No!
But here’s the same Dean Smart at Flynn’s parole hearing in March, during an extraordinary and moving back and forth between the two men.
If he does get out, I’d like to see him do something great with the rest of his life. He has a great opportunity to start a new life…
He can do something great, he can be a saint, he can turn it around. He can redeem himself with great actions, hopefully, to erase the evil things he’s done.
I hope he does that. I hope he gets out, and he does something great with the rest of his life…
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