Billy Flynn Wiki: The Lovestruck Teen Who Shot Pamela Smart’s Husband

Billy Flynn was just 16 years old when he and three of his friends participated in the murder of Greggory Smart, 24, on May 1, 1990. Gregg was married to Pamela Smart, then 22; she was having an affair with the impressionable Flynn and said the only way they could continue to see each other is if her husband was out of the way. Billy Flynn was convicted of second-degree murder and was released from prison on June 4, 2015. Pamela Smart was convicted of first-degree murder and is serving a life sentence.

To learn more about this love affair gone awry, the shocking death of Greggory Smart, and the trial that captured the country’s attention, read this Billy Flynn Wiki.

About William Billy Flynn
Age44 Years
BirthMarch 12, 1974
GenderMale
SpouseKelly 2006-Present
ParentsBilly Flynn, Elaine Flynn
MurderedGreggory Smart
Prison Sentence Served1991-2015

Who Is William “Billy” Flynn?

William “Billy” Flynn was born on March 12, 1974, to Billy and Elaine Flynn. Their marriage was, to say the least, strained and tumultuous, with young Billy often caught in the middle.

Eventually, Billy was on the receiving end of his father’s anger.

The couple would go on to have two more sons, but Billy was always the one Billy Sr. focused his anger on.

“If things were going my husband’s way, he was a great guy to be around,” said Elaine Flynn. “But as soon as he had to deal with any inconvenience, forget it.”

Billy Flynn

Billy Flynn (1991); https://www.youtube.com/watch?v=2kXKJA0SLIU

Elaine recalled how the family would go into the nearby canyons on dirt bikes. Unfortunately, the bikes always seemed to have mechanical problems.

“Well, once Billy had a problem with his bike,” she said. “It was something as trivial as a spark plug. His dad told him how to fix it and it didn’t go. It was blow-up time. His father would start yelling, ‘You couldn’t have done what I said!'”

Life Gets Tougher for Billy Flynn

The year 1986 was a tough one for 12-year-old Billy Flynn. His mother decided to leave her husband after discovering he had been cheating on her for years. Not surprisingly, the Flynns’ marriage imploded and the couple divorced.

Elaine picked up and moved the family from California to South Seabrook, New Hampshire. Billy was just entering junior high and didn’t want to move.

“He was an angry little guy coming back with me,” Elaine recalled. She enrolled Billy in seventh grade at Seabrook Elementary School.

It was here that Billy would meet his best friends, J.R. and Pete.

The three kids are remembered as being more than just a little rough around the edges. On the plus side, Billy had found a group of friends he connected with. In fact, William “Billy” Flynn, Patrick “Pete” Randall, and Vance “J.R.” Lattime, Jr. were so tight they were referred to as the “Three Musketeers.”

And not just because they hung out all the time. The Three Musketeers were also known to be quite helpful in the neighborhood where they lived. They ran errands, shoveled snow, and would tackle odd jobs. They also gave the local elderly residents free services or large discounts.

A Freak Accident

Two months before Billy turned 13, his father died in a freak accident. A car pulled in front of him; he veered to avoid an accident and ended up running into the rear end of a gasoline tanker carrying 9,000 gallons of fuel. There was nothing left of Billy Sr. except his teeth.

Young Billy withdrew after the death of his father, spending a lot of time on his own. He was also acting out at home.

“It was not that Billy was violent,” his mother Elaine said. Billy didn’t have any impulse control problems, but he would get angry over the smallest things, making it difficult to communicate with him.

“Outside of the family, people saw a kid that was polite and charming,” she recalled. “That was one side of Billy that he projected to people that he wanted to impress. He wanted to be liked. Inside the family is where he took out his anger. He has an attitude when something’s bothering him…It’s like a volcano waiting to erupt.”

It was during this period in his life that he would meet Pamela Smart.

When and How Billy Met Pamela

Billy Flynn met Pamela Smart in the fall of 1989 while he was a freshman at Winnacunnet High School. Pamela, who was 22 at the time, had received her BA in communications in 1988 and was pursuing a job in broadcasting; she was doing everything she could to help pad her resume.

She volunteered as an adult facilitator with Project Self-Esteem, a local drug awareness program. All freshmen at Winnacunnet High School were expected to participate in the program. Pamela hit it off with the students fast.

She was young, pretty, and loved heavy metal music. It’s debatable whether the self-esteem project was successful, but everyone liked Pam. Unlike most adults and other teachers, she never looked down on her students or patronized them.

Pamela Smart

Pamela Smart;; Image: https://www.youtube.com/watch?v=ZoCNQtkrWeo

She spoke to them as if they were her peers and shared the same musical tastes as many of the students. Instead of lecturing them, she waxed about meeting Eddie Van Halen and rubbing shoulders with other heavy metal icons she met backstage.

Cute and loved heavy metal. It’s all Billy Flynn needed to see. After being introduced to Smart the first time, Billy Flynn turned to his friend and said, “I’m in love.” And indeed, he was smitten with Smart. He went out of his way to be helpful during the sessions and would visit her every day at her office.

She would hardly admit it at the time, but Billy Flynn, despite the eight-year age gap, was the kind of guy Smart was into. He was 5’11”, 150 pounds, with shoulder-length hair, an earring, played guitar, and resembled a young Paul McCartney. It didn’t hurt that Billy Flynn was into heavy metal, especially Mötley Crüe.

The pair continued to spend time with each other after the program ended, working on an orange juice video competition.

Pamela Smart’s Marriage Troubles

Billy Flynn’s infatuation with Pamela Smart and her marriage troubles would be a lethal combination.

Pam and Gregg Smart

Pam and Gregg Smart; Photo: Investigation Discovery

It was around this time that Pamela’s husband, Gregg, confessed to Pam that he was having an affair. The revelation came less than a year after they married.

An affair might immediately kill most marriages, but the Smarts continued to work on theirs. Albeit, there were many, many road bumps. Every time they had a fight, Pamela would bring up the affair. “I didn’t feel as important anymore,” Pam would later say. “Obviously it affected my trust.”

Clearly. Gregg was becoming more dedicated to his job as a successful salesman for an insurance company and Pamela simply wanted out of her marriage. She was given a hall pass, too. For some odd reason, Gregg encouraged Pam to spend more time with the students she had become friends with.

The Affair

While at Winnacunnet High School, Pamela Smart also became friends with another student, Cecilia Pierce, who was also friends with Billy Flynn. The new Three Musketeers spent a lot of time together, hanging out at the mall, restaurants, beachfront arcades, and clubs.

Gregg was spending more and more time at work and with friends, and Pam was spending more and more time with Billy. Some might think spending time together after school in public places was crossing the line, but that line would soon be a distant memory.

One winter afternoon in February 1990, Billy was in Pamela’s office. Both of their hormones must have been raging.

“Do you ever think about me when I’m not around,” she asked?

“Yes,” he admitted.

“Well, I think about you all the time,” Pam said.

Billy’s dream had come true. Billy was hot for teacher and she was hot for him. Billy’s life had been marred by an unwanted move and the death of his father, but Pamela Smart, a woman he was deeply infatuated with, had now entered his life.

Billy Seduced by Pamela

In late March 1990, Gregg went out of state for an insurance meeting. She invited Billy and Cecilia over to their condo at 4E Misty Morning Drive in Derry, New Hampshire, to watch movies. On tap that night was 9 ½ Weeks, starring Kim Basinger and Mickey Rourke and their steamy kitchen floor sexual antics.

It was impossible to resist.

Cecilia eventually left to walk Pamela’s dog, Halen (as in Van Halen). Pamela, without breaking a sweat, enticed Billy upstairs to her bedroom. She slipped on a turquoise negligee she bought for the occasion, put Van Halen in the CD player, and, for the first time, had sex with Billy.

Pamela Smart

Pamela Smart; Photo: https://www.youtube.com/watch?v=UTs08KvAbbs

Cecilia eventually returned, got bored waiting for the two of them to return, and walked upstairs. She found Billy and Pamela tangled up on the bedroom floor having sex.

Billy Flynn Thought Pamela Smart Was Worth Killing for

The next morning, Billy Flynn was riding high from his sexual initiation into Pamela Smart’s world. As she drove them to school, Pamela looked at Billy, “Last night was great, but we can’t keep on like that.”

“Why not,” a confused Billy asked?

“Because of Gregg. If you want to keep seeing me, you’ll have to get rid of my husband.”

That wasn’t entirely true. They continued to meet up for sex over the ensuing weeks. But Pamela persisted, “You have to get rid of Gregg. Otherwise, we can’t keep on seeing each other.”

Wise beyond his years, Billy would ask Pamela why she couldn’t just get a divorce. Pamela claimed Gregg would follow her anywhere and everywhere and she would never be able to have a boyfriend. On top of that, she would lose the condo, furniture, and Halen.

Pamela also falsely claimed that Gregg beat her. The only way out was to kill him. Gregg’s death would give Pamela life. And insurance money.

Billy Flynn Gets Instructions from Pam on How to Kill Gregg

To love Pamela Smart is to kill for Pamela Smart. Billy wasn’t keen on the idea, but he still agreed to do it. Even then, it took some convincing.

Gregg Smart

Gregg Smart; Photo: https://www.findagrave.com/memorial/7090228/greggory-w.-smart

Billy aborted two attempts to kill Gregg. Pamela was not pleased and threatened to break up with him if he fell short a third time.

“If you loved me, you’d do this!” Pamela screamed at him.

“I told her I did love her,” he would later testify.

“That’s when I started getting serious about it,” Billy recalled. Because I thought that if I do something like not go up or anything again, she’s gonna leave me and that’s gonna be it. So this is the time that I really started talking to J.R. and Pete about it.”

Billy knew he could no longer put off killing Gregg. And Pamela even provided him with the date.

Pamela told Billy that May 1, 1990, would be his last chance. Gregg had a late appointment that night and she would be busy with a school board meeting. To further entice Billy, Pete, and J.R., she promised to give them some insurance money once it was paid out.

The plan to kill Gregg was pretty straightforward. The boys would wear dark clothing, Pamela would leave the cellar and rear doors open, and Billy and Pete would ransack the place (staging a robbery but could still take whatever they liked).

Pamela also gave them three instructions they had to follow.

  • Don’t turn on any lights: Pam said Gregg was “a real wimp—if he sees a light on, he won’t come inside.”
  • Don’t hurt the dog: Pamela wanted Halen put into the basement. “She doesn’t want Halen to be traumatized.”
  • Use a gun rather than a knife: For obvious reasons, a knife would leave blood on her white leather couch.

Pamela then asked the three boys how she should act when she discovered Gregg’s lifeless body on the floor. Scream, cry for help…?

“Just act natural,” one of the boys told her.

Billy Flynn Ambushes and Murders Greggory Smart

May 1, 1990, started out like any other day for Gregg Smart. Gregg got up early, had a shower, coffee, and made small talk with his wife.

For Pamela, however, it was anything but a normal workday.

For her part, Pamela was usually the first one out the door, but not that day. She left later than usual, at around 9:45 a.m. She wore all of her gold chains and a ring on every finger, just to make sure she would not lose one of her favorite pieces of jewelry during the heist that evening.

She drove her Honda CRX with a New Hampshire vanity plate that read HALEN to school, knowing she’d be home later than usual that evening. The school board meeting was going late, discussing a salary review and a media class Pamela was interested in teaching the coming fall.

During the day, Pamela dropped by Billy Flynn’s locker to let him know that she left the doors open. Later that afternoon, at around 2:30 p.m., Billy called Pamela to tell her they needed a ride to go pick up the getaway car, J.R’s grandmother’s yellow 1978 Chevrolet Impala. She acquiesced.

The Evening of May 1, 1990

Before 8:30 p.m., Billy Flynn and Pete Randall entered the condominium on Misty Morning Drive.

Their first task was to get Halen into the basement. He put up a fight and scampered off. They eventually caught him and tossed him into the basement, listening to the thud-thud-thud of Halen as he tumbled down the stairs.

The two boys then ransacked the house, taking jewelry and disassembling the entertainment center.

They then lay in wait for Gregg to come home. Billy had a snub-nose revolver tucked into his waistband. The third Musketeer, Lattime, had taken the gun from his father’s collection. Randall held a long-handled knife he’d picked up from the kitchen.

The pair decided that Pete would hide behind the door where Gregg couldn’t see him and Billy would hide on the stairs. When Gregg opened the door, Pete would pull him inside and they’d both jump him with Pete holding a knife to his throat.

Pete Randall

Pete Randall (1991); Image: https://www.youtube.com/watch?v=9gX0Iqz8r04

Not long after, headlights hit the house with Gregg’s pickup pulling up to the condo. Billy and Pete, confused in their excitement, reversed their agreed upon places, with Billy behind the door and Pete on the stairs.

Gregg turned the truck off and walked up to the door. He put his key into the lock and opened the door, calling out into the dark, “Halen!”

Billy leaped out, grabbing Gregg by his shoulders. Pete joined the melee.

Gregg, believing he was being robbed, handed them his wallet.

Pete then told Gregg to give them his wedding ring, “No! I can’t do that. My wife would kill me!”

Pete Randall forced Gregg onto his knees in the foyer, holding the knife to his throat.

Billy said “God forgive me!” and squeezed the trigger, just inches from Gregg’s head. Gregg slumped over, shot in the head.

Billy and Pete ran out of the condo and into the waiting getaway car.

Pamela would later tell Billy that while driving home that night she actually saw them driving and flicked her lights at them in greeting.

Billy Flynn

Billy Flynn; Mugshot: https://www.youtube.com/watch?v=UTs08KvAbbs

10:10 p.m., Pamela Smart Shocked to Find Husband Dead!

Pamela Smart returned home that night. She noticed the house was dark—a good sign since Gregg usually turned the porch light on when he got home so she wouldn’t have to walk up to the house in the dark.

She parked in the garage and walked up the front porch of the condo, unlocked the door, stepped inside, and flicked the hallway light on.

Alarmed (as per her later report to the police), Pamela saw her home had been ransacked and her husband Gregg, murdered.

Police initially said the crime scene looked like a disrupted burglary. Gregg was lying face down in a pool of blood; killed execution-style.

His body was found mostly on the blue wall-to-wall carpet of the dining room, his splayed feet and ankles resting on the front hallway floor. A 38-caliber hollow-point slug had ripped into his head just above the left ear.

Under Gregg’s body was his diamond studded wedding ring, keys, and wallet. Two stereo speakers and a TV were left near the back door.

“My husband’s hurt! He’s on the floor!” Pam shouted. “I don’t know what’s wrong with him!”

Neighbors came rushing over, with at least two calling 911.

Two neighbors hurried over to their condo and opened the door; 10 feet away lay the body of Gregg Smart.

The Investigation

It didn’t take long for local police to think something wasn’t right.

“The scene stunk to high heaven,” Derry Police Capt. Loring Jackson recalled. “Not much was making sense. No sign of forced entry? A nighttime burglary in a densely populated area? An execution-style killing?”

Jackson didn’t think it was a burglary. There we no signs of a struggle. Burglars don’t usually fight, and they generally don’t carry guns. Burglars rarely kill and, when they do, it’s not execution-style.

The first person investigators look at with a domestic homicide is the spouse. In this case, Pamela Smart had an airtight alibi. She was 35 miles away at a school meeting.

Still, Detective Daniel Pelletier, then 28, found her behavior odd.

“From day one,” he said, “she wasn’t acting the grieving widow.”

Pamela insisted on going down to the police station and making a statement. “This looks like a botched burglary,” she said. “The first thing I saw was the speakers off the stand.”

Pelletier remembers looking at a colleague thinking: the first thing she saw was the speakers? What about her husband on the floor?

Then, Pamela said, “When I walked over to the body…”

Another red flag. “Not ‘my husband,’ but ‘the body’?”

Pelletier knows people grieve in different ways so he gave her the benefit of the doubt.

Three days later, though, all of that went out the window.

He accompanied Pamela Smart to the condo to pick up some items. Smart walked into the house and casually across the blood-soaked carpet where Gregg’s bloodied head had lain. Not just once, either–repeatedly.

Pamela’s mother eventually placed a towel over bloodied area, but Pamela continued to step on it. Everyone else, though, walked around it.

Two weeks into the investigation, police received an anonymous tip that confirmed what they believed: Pamela Smart had orchestrated Gregg’s death with the help of three teenage boys.

Pamela Smart

Pamela Smart’s Mugshot; Photo: https://www.youtube.com/watch?v=ZoCNQtkrWeo

Pamela Smart Arrested

At 1:05 p.m., on Wednesday, August 1, 1990, Det. Pelletier entered Pamela Smart’s office.

“What’s up?” she asked.

“Well, Pam,” he replied. “I have some good news and I have some bad news. The good news is that we’ve solved the murder of your husband. The bad news is, you’re under arrest.”

“What for?” she said.

“First-degree murder. Stand up and face the wall.”

It was her last day of freedom. Pamela was arraigned in Derry District Court and jailed. She has been behind bars ever since.

Pamela Smart

Pamela Smart (2015); Image: https://www.youtube.com/watch?v=vjDw7FbQ08E

The Trial of Billy’s Lover

The March 1991 trial was one of the most sensational in New Hampshire history. It was also the first to be nationally televised live. Every lurid detail. And had higher viewership than afternoon soap operas.

Pamela Smart admitted to having an affair with Billy Flynn, but denied planning to kill her husband. And if she was going to, she certainly wouldn’t get the help of teenage boys, she said.

The most incriminating testimony came from secret recordings taped between Pamela and her one-time friend Cecilia Pierce and the three co-conspirators. All three of the latter, including Billy Flynn, secured their own plea bargains before the trial even began.

Cecilia Pierce

Cecilia Pierce; Image: https://www.youtube.com/watch?v=CCM0pvTExOo

The 14-day trial came to an end on March 22, 1991 (less than two years after Billy and Pamela first met). The jury deliberated for 13 ½ hours, finding Pamela Smart guilty of “being an accomplice to first-degree murder, conspiracy to commit murder, and witness tampering.” She was handed a mandatory sentence of life in prison without the possibility of parole.

Pamela is serving her sentence at the Bedford Hills (N.Y.) Correctional Facility for Women.

Billy Flynn: A Model Prisoner

Billy Flynn and Peter Randall turned state’s evidence in January 1991, two months before Pamela Smart’s trial began. In exchange for helping police, Billy’s charge was reduced from first-degree murder to second-degree murder.

Flynn, Randall, and J.R. Lattime were all sent to the Thomaston State Prison in Maine.

Flynn and Randall were eligible for parole in 30 years, with 12 years suspended, making them eligible for release in 2008.

Lattime’s sentence was reduced by three years, making him eligible for parole in 2005.

Flynn was described as a model prisoner who earned his GED. In 2002, he got certification as an electrician’s assistant.

After getting the certification, he worked as an employee of the Maine State Prison’s electrical department where he earned rave reviews. State records show he earned his journeyman electrician’s license in July 2014.

Billy Flynn also joined a prison ministry group and worked in prisoner support groups and on a Toys for Tots program in the Rockland area.

In 2008, one correctional officer said of Flynn that he had “grown from a confused teenager who made an egriegious mistake into a responsible, caring individual that would be a positive addition to any community, whether inside or outside a fence.”

Billy Flynn

Billy Flynn (2008); Image: https://www.youtube.com/watch?v=2kXKJA0SLIU

Billy Flynn Marries While in Prison

While in prison, Billy Flynn began corresponding with a woman by the name of Kelly. After communicating for six years, the couple married in 2006. Billy is also now stepfather to Kelly’s daughter from a previous marriage.

During a February 2008 request for a suspended sentence, Kelly wrote, “The more I got to know Bill, the more I realized that he was not the same person who became involved with Pam Smart at the tender age of 15.”

“I am not naive, but a 39-year-old woman with a teenage daughter (13), so I know there will be adjustments for all of us, and some of them may be hard.”

“Whether you decide that he gets out now, in a few years, or in many years, my commitment to him will not change. I am in this for life, because without him, I would have less in my life and when I think of my future, I cannot see it unless it includes him. He is the heart of me,” she added.

Billy Flynn Paroled from Prison

Kelly did have to wait for Billy to be released from prison. But he was still eventually released.

On June 4, 2015, Billy Flynn was released from prison after serving almost 25 years for murdering Gregg Smart.

He was the last of the three friends to taste freedom.

Both Billy Flynn and Pete Randall remain on lifetime parole.

Pete Randall

Pete Randall (2015); Image: https://www.youtube.com/watch?v=9gX0Iqz8r04

A spokesperson for Pamela Smart said it’s not fair that Billy Flynn and Pete Randall, two men who admitted to killing Gregg Smart, are free while she is stuck in prison, with zero chance of parole.

Commenting on the release of Flynn and Randall, Dr. Eleanor Pam, a supporter of Pamela Smart and wife of Smart’s attorney, said, “Over and over they have been rewarded for their expressions of contrition for killing Greggory Smart. But it is one thing to say you are remorseful and another to be remorseful.

Pamela Smart, on the other hand, has been condemned and punished for her failure to admit any role in the murder of her husband … But how can anyone take responsibility for a crime they did not commit?”

It is not known where the married couple resides but Billy will remain in Maine; Kelly lived in Newcastle prior to her husband’s release.


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