Case 352: Gregory Smart

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And so it was like to go to the online shop. If you buy a shopping trip, then you will get the platform that is actually a trip. It is simply the main thing. Our whole business is going to be on shopping. Now let's start a shopping trip. Our episodes deal with serious and often-distressing incidents.

“If you feel at any time you need support, please contact your local Crisis Center.”

For suggested phone numbers for confidential support and for a more detailed list of content warnings, please see the show notes for this episode on your app or on our website. On the night of Tuesday, May 1, 1990, a group of family and friends gathered at a home on Misty Morning Drive in the town of Derry, New Hampshire. At around 10pm, as they broke out into a joyful rendition of Happy Birthday, their celebration was abruptly cut short by a blood curdling screen. Fred Lombardi, the host of the party rushed outside to see what was going on.

Disturbing says were rare on the quiet Kota sack, which was largely made up of condominium occupied by young couples.

“As Fred stepped into the street, he almost collided with his 22-year-old neighbor, Pamela Smart.”

Pamela had been running away from the unit she rented with her 24-year-old husband, Gregory. What is it? What's the matter? What's happened? Fred asked. Pamela frantically replied, "It's my husband, he's been killed, he's dead." As Fred began moving toward the Smart Residence, Pamela grabbed him and yelled, "No, don't go in there, it wouldn't do any good, he's dead, I know it." Fred persisted saying he wanted to help, but Pamela begged him not to. "Please," she said. "Don't go in there, just call the police."

The first officer to arrive on scene observed Pamela Smart kneeling on the stoop of a neighbouring home, sobbing.

Onlookers directed him to the Smart's unit. Inside, the foyer light eliminated Gregory Smart, dressed in grey pants and a matching sports coat. He was lying face down with his feet on the tiled foyer floor and the rest of his body on the carpet in the adjoining dining area. A small amount of blood had poured beneath his nose. As the officer went to roll Gregory over to begin CPR, he noticed a large fatal wound on the upper left side of his head.

No one else was found inside the residence, which had been ransacked. Cds were scattered everywhere. A VCR was overturned on the floor, and stereo speakers were placed by the back door along with the small television. It appeared that a burglar had been piling their loot there in preparation to flee when they were interrupted by Gregory arriving home. He was shot once in the head at close range, killing him instantly. The main bedroom upstairs was also in disarray.

Drollers had been poured out, clothing was tossed about, and an empty jewelry box was found in the bathroom sink.

One less harp hazard than the other.

“Pillow stuffing was found throughout the unit, and several sofa pillows were missing, suggesting they had been emptied and used his bags to carry stolen goods.”

The smart small pet dog, which usually roamed freely throughout the residence, was found locked in the cellar. Behind the condominium was a grassy hill leading to parkland, commonly used as a shortcut to a nearby shopping plaza. About 100 yards from the smarts condo, in a mode area, police found a carving knife embedded in the ground, along with paper towels, a plastic jewelry box, and parts of a cardboard jewelry box, all of which had come from the smart residents. During an interview with police at that night, Pamela Smart stated she worked as a medial coordinator for school administrative unit 21,

which oversaw several school districts across the state.

Her office building was across from Winnecun at high school, just under an hour's drive from her home. Gregory worked as a salesman for his father's insurance firm, and left home that day at 9am.

“Pamela left at about 9.45, slightly later than usual, because she was attending a school board meeting that evening.”

When she returned home at around 10.10pm, Gregory's pickup truck was parked outside, but the internal house lights were off, and the front door was locked. Upon entering the unit, Pamela turned on the FOIA light and discovered Gregory's lifeless body. There was no sign of forced entry around the unit, but Pamela suggested the rear French doors might have been left unlocked after a recent gathering. Investigators also found the bulkhead leading to the cellar unsecured. Given that the smarts didn't usually leave lights on when they were away, Gregory likely entered the dark unit without sensing any danger.

Pamela was cooperative with investigators and willing to assist them in any way. However, they noted that she was unusually composed for someone who had just found her husband brutally murdered.

“She didn't cry during questioning and appeared more anxious than distressed.”

Her eyes frequently moved around to the room and she seemed tense. Investigators spoke with Pamela again the following day. She was just as calm and collected as the night before. They assured her that they meant no offense, but they needed to know if she and Gregory were experiencing any problems such as financial difficulties, drug or alcohol issues or infertility. Pamela said no, she and Gregory had only been married for a year and both had been doing well.

She had just received a $26,000 pay rise and was enjoying her work viewing it as a stepping stone toward a career in broadcasting. Gregory had recently co-want a rookie salesman of the Year Award. Outgoing and sociable, he had no known enemies and was widely described as the kind of person who would give someone this shirt off his back. The pair had met in 1986 at a New Year's Eve party Gregory was hosting. He was a long-haired, good-looking metalhead, contrasting with Pamela's image as a petite popular cheerleader.

But she had a hidden edge. She enjoyed the same type of music as Gregory and the two quickly hid it off and went on several dates. Pamela quickly developed strong feelings for Gregory, but at the time he wasn't ready to commit to a serious relationship. The two remained in contact after Pamela left for college and months later she visited Gregory and discovered he was casually saying someone else. Pamela forced him to choose between her and the other woman.

To her surprise and disappointment, Gregory ended their relationship on the spot, still unwilling to commit. That summer they crossed paths again during a vacation with mutual friends. Their romance rekindled and Gregory began having serious feelings about Pamela.

She was thrilled when he finally agreed to move in together and get engaged.

The wedding was an extravagant event attended by more than 200 guests. By all accounts it went perfectly, yet those who knew Gregory well were surprised that his decision to marry at a young age. He had typically been the life of the party and not someone who appeared eager to settle down.

Even so, then newly wedded couple appeared happy when they left for their honeymoon.

“But once they returned, the critical side of Pamela's personality started to cause friction in the marriage.”

As a wedding present, her family had given the couple substantial amounts of cash and expensive items. Pamela was annoyed that Gregory's family had contributed comparatively little in some cases barely enough to cover the cost of their meal. Unlike Pamela, who had a more distant relationship with her family, Gregory was very close to his own. He grew irritated by her complaints and eventually told her he'd heard enough.

But she wouldn't let them let go.

Pamela was known to make sharp or cutting remarks that left others feeling hurt in order to elevate herself by comparison. Some believed this behaviour stemmed from deep-seated insecurities, despite Pamela being widely regarded as physically attractive, popular and successful.

“These traits also made her competitive and possessive, with others describing her as someone who harbored a simmering anger beneath the surface.”

Gregory took amusement in provoking his wife with passive aggressive acts, including deliberately mispronouncing her name, and making suggestive comments about other women. Whenever Pamela tried to confront Gregory or draw him into an argument, he dismissed her frustrations with a simple "whatever", which only infuriated her further. The couple's strong ego-driven personalities often clashed as did their differences.

Pamela was ambitious, determined and highly organized, always planning for the future.

Gregory was laid back, carefree, and content to spend his time kicking back with friends. Pamela also grew unhappy that Gregory, who had flexible work hours, was often away from home in the evenings.

“Gregory told a friend that Pamela wanted him to quit his job, but he refused as he enjoyed his work and the income had provided.”

Given that much of his free time was spent with friends pursuing hobbies such as playing cards, golfing and offroading, activities Pamela had little interest in, the couple spent relatively little of their leisure time together. Pamela focused on her own interests, including taking courses related to media and public relations, and reading upwards of six newspapers a day. She had dreams of becoming a nationally recognized reporter, just like the anchor women and a journalist she admired. Many people in the smart social circle were completely unaware of any serious issues in the marriage.

For the most part, the couple presented themselves as coping fine and capable of recovering from their disagreements. They would regularly go out for dinner or drinks with friends, host gatherings at their home, and were planning a vacation together. Gregory had even mentioned that he was preparing a celebration for their one-year wedding anniversary. Yet, there were some who still believed the marriage was doomed to fail. Both Gregory and Pamela had confided in others about fundamental issues and differing expectations for the future.

Gregory wanted the by-house and have children, but Pamela wasn't interested. While venting with a friend about the problems they had with their respective partners, Pamela asked, "Why can't they just die and make our life easier?" No divorce, no nothing, just disappear. Gregory's murder occurred just days, shy of his and Pamela's one-year wedding anniversary.

The only moment Pamela's stoic demeanor shifted during her early conversations with police was when they advised her not to speak to the press. She became noticeably defensive, saying, "Don't talk bad about them. I'm one of them too." Investigators found it odd that she seemed to more upset by their comments about the media than by her own husband's brutal and untimely death. Pamela's behavior raised further suspicion once police had finished processing the crime scene. As they prepared to leave the unit, she was allowed inside to collect clothing for Gregory's funeral.

A towel had been placed over the bloodstain in the dining room to spare her from seeing it, and she stepped across it nonchalantly.

When she went upstairs to select the clothes, Gregory would be buried in, she moved quickly and without hesitation, opening drawers and grabbing whatever was there.

“She took no time to pause, mourn, or reflect. Nothing she selected even matched.”

It was only after she stepped outside that she finally broke down in the presence of Gregory's parents.

Investigators spoke to the smart neighbours, and only one record hearing anything unusual on the night that Gregory was killed. He had heard Gregory arrive home at around 9pm, followed by the pitipatter of feet across the floor, and then two loud thuds, which came several minutes apart, and sounded like door slamming. The decision to target the smart unit was strange. Breaking into a densely populated condominium complex at night, when most residents were likely to be home, was reckless. Such risky behaviour was more commonly associated with amateur opportunistic offenders who were typically unarmed.

“Those who did bring guns rarely used to them, let alone to deliberately execute an innocent person in cold blood.”

They were also the type to steal small, easily pocketed items that they could immediately use cell or discard, such as wallet's keys into jewelry, rather than large bulky electronics.

But Gregory's diamond and gold wedding ring was found underneath his body, and his wallet and car keys were left between his legs. There was no cash in the wallet, but all of his credit cards were inside. If more experience defenders were responsible for Gregory's murder, investigate his question why they abandoned the job and left behind much of the property they had gathered to steal. As for suspects, there were few obvious leads. Gregory enjoyed taking trips toward Atlantic City with friends and family where he gambled.

“Investigators wondered whether he could have accumulated deaths with the wrong people.”

Neighbors also reported in increasing parties and get-togethers at the smart unit in recent weeks, with a variety of people coming and going from the residents.

Some were noted as looking suspicious. This prompted speculation that drugs might be involved. The theory gained some traction when a cannabis cigarette was found in Gregory's pickup truck. However, no other illicit substances were discovered in his vehicle, unit or anywhere else on the property, and he had no prior history of major drug use saw interactions with the police.

Whatever the explanation, investigators increasingly suspected they were dealing with something more than a burglary gone wrong. Against investigators' advice, Pamela Smart spoke to the press about her husband's case. She said she wanted to dispel the growing rumours that the killing was drug-related, insisting that she simply wanted the truth to be known. While details of the crime were being kept under wraps to protect the integrity of the investigation, Pamela openly disclosed some of the confidential information during a film to media interview.

She described the crime scene in considerable detail revealing that the unit had been ransacked. That stereo speakers had been left by the back door, and that $300 worth of jewelry was missing. She also referred to the theory that the killing was a botched burglary, and stated that there were no witnesses. The interview took place on the day of Gregory's wake. At the event, Pamela received an outpouring of support from those in attendance.

She also announced that she had established a memorial fund in Gregory's name to purchase equipment for a mass media course at Winniacun at High School. The class was a recent addition to the school, having been approved during the board meeting held on the night Gregory was murdered, the same meeting Pamela had attended. Notably, she had been selected to teach the course. Pamela explained that she wanted something positive to come from the tragedy and for Gregory to remain a part of her daily life.

During the wake, three students from Winniacun at High School arrived with a guidance counselor. Having heard about Gregory's tragic death, the counselor believed it would be appropriate for the students to pay their respects, as they were all well acquainted with Pamela.

Cecilia was a student intern in the media center who worked directly with Pamela, while Billy had recently received assistance from Pamela for a videotape competition at school.

“Vance was less familiar with Pamela than the other two, but still closer to her than most.”

Pamela appeared surprised to see the three teenagers whose presence at the wake could drew some attention, but she thanked them for attending. She introduced to them to several people and spent a short time speaking with them. At one point, Billy and Vance approached Gregory's casket and knelt beside it. The group remained at the wake for less than 15 minutes before leaving. More than 200 people attended Gregory's funeral.

Among them were investigators keeping watch for anyone who might appear suspicious, but once again, it was Pamela who drew their attention.

“During the service, she asked Gregory's father whether he had requested a full or half mass.”

He didn't understand what she meant, prompting Pamela to explain that she had instructed the priest to make it short. As she left the church, where members of the media had gathered outside, Pamela appeared more openly grief-stricken. Before being driven away, she rolled down her car window and cheerfully told reporters. I'd just like to say, Gregory was the kindest person I ever knew. He was a really good friend of mine, and he didn't deserve this.

At the burial, Pamela placed a single rose on Gregory's coffin.

“Inside, a framed photograph of the young couple on their wedding day rested in his hands.”

Pamela continued to assist the police investigation by providing any requested information, including names of individuals Gregory was associated with. She was overly eager to help, often over supplying irrelevant details that police had announced for, which only served to muddy their work. Furthermore, Pamela's continued willingness to speak to the press and disclose sensitive information was an ongoing issue. One investigator even contacted Pamela's father and asked him to speak with her about her behaviour.

Eventually, they decided to stop updating Pamela on the case altogether.

Report is frequently contacted Pamela for comment, and she never declined the opportunity to be interviewed.

Each time she emphasized that Gregory's death was the result of him interrupting a burglary. She also maintained that Gregory didn't have any enemies, and described his killer as a quote, drug addict person looking for a quick $10. If she knew who it was, Pamela said it would have been the first name she gave to the police. While some thought Pamela's unusual behaviour was simply an irrational response to grief, others suspected she couldn't resist the attention, having always been drawn to the spotlight.

Report is noted that Pamela showed a little visible emotion when speaking about her husband or his murder. Her interactions with them also felt controlled, with observers suggesting she was drawing on her media training to manage her public image. On what would have been the smarts one year wedding anniversary, an article about the case was published in a telegraph under the headline, but Pamela's smart, life must go on. In it, Pamela maintained that she and Gregory had been happy with no problems, and that they simply wanted to be together.

She said Gregory was the kind of person who would reassure her that things would always work out, and that she was now drawing on that sentiment as a way to cope and move on with her life.

Pamela delivered Gregory's personal belongings to his parent's home without ceremony. Among the items was a piece of wedding cake that couple had stored in their freezer for a later occasion, which she handed over, saying, "Here, you take this. I don't like cake anyway." She then invited friends over to her unit and began giving away the rest of Gregory's things. She served lunch and spoke joyfully within steps of the bloodstain in the dining room, which still hadn't been cleaned. Pamela then began looking for a new car, intending to use part of Gregory's $140,000 life insurance payout to purchase it.

One night while watching a band she liked, Pamela got up on stage to sing with an ex-boyfriend.

“Afterwards, she gave him her number and urged him to visit.”

She was also witnessed the dancing up against other men, and in a flippant matter-effect manner, told other revelers that her husband had been murdered. Meanwhile, investigators distributed flyers featuring images of the jewelry stolen from the smarts to pawn shops. They pursued a range of leads, including a criminal group posing as police officers to gain entry to homes and a former jilted lover of Gregory's. But none of these leads went anywhere.

A significant development finally emerged on Monday, May 14, two weeks after Gregory's smarts murder.

That night, the dairy police department received an anonymous phone call. Case fire will be back shortly.

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Thank you for listening to this episode's ads. By supporting our sponsors, you support Case File to continue to deliver quality content. The caller was a nervous-sounding woman. While she said she didn't want to get involved, she felt compelled to pass on information she had heard, even if it was just hearsay. Speaking of Gregory's smarts murder, the woman stated, "He's wife planned him to be killed."

She claimed Pamela's smart had been putting on a wonderful performance since, with the motive being Gregory's life insurance money.

“The tipster admitted that she had obtained the information second hand from a minor, eventually revealing it to come from a 15-year-old girl.”

While she refused to name the girl at first, after some gentle probing from the detective, the woman said the girl was named Cecilia Pius.

She said Cecilia was friends with Pamela, and she had attended Gregory's funeral. She then hung up. Investigators discovered Cecilia Pius was a student at Winnecun at High School. She had worked with Pamela's smart as a student intern in the media center, and had attended Gregory's wake. Further inquiries showed that Cecilia had also visited Pamela at her condo the week before Gregory's murder,

a meeting Pamela didn't initially disclose to the police. Cecilia's name was also notably absent from the list of acquaintances that Pamela initially provided to investigators. It appeared only later about a week after the murder, in a separate list of friends of Pamela's that she didn't share with Gregory.

Talkative and friendly, Cecilia Pius first introduced herself to Pamela's smarter school. Sicilia wanted to bear reporter, but was somewhat of an outcast among her peers for being overweight,

living in a rough area, and having a difficult home life. Her parents were divorced, and her mother struggled to support Cecilia and her younger sister. Cecilia viewed 22-year-old Pamela's smart as the kind of person she aspired to be, good-looking, successful, and confident. When Cecilia mentioned an interest in journalism, Pamela suggested she work in the school's media center as her intern. Cecilia gratefully accepted and began visiting Pamela's office for two periods a day, receiving credit for assisting with tasks such as writing the school board newsletter.

She became increasingly comfortable in the role and came to value Pamela's attention and friendship. Pamela had a tendency to make others feel wanted and heard, which Cecilia appreciated.

She began to confide in Pamela and viewed her as a role model and older sister figure.

“One day, Cecilia noticed a flyer on Pamela's desk advertising a high school video competition for students.”

The task was to make a commercial promoting the nutritional value of orange juice, with prizes including a trip to Disney World. Cecilia asked some other students if they wanted to help submit a video.

Fifteen-year-old Billy Flynn wasn't very interested at first, but ultimately agreed to help out, mostly behind the camera.

Billy came from the same rough area of Cecilia and also had a difficult home life. His father was abusive and as the oldest of three boys, Billy was treated the harshest from an early age. When his parents eventually divorced, his mother moved him from California, which he found difficult to adjust to. Not long after Billy enrolled at Winni-Cun at High School, his father died in a car crash.

“This had a strong emotional impact on him and he became more with the drone.”

Even though he seemed to like a defiant rebel, with these long hair, leather jacket, ear piercing, love of metal music and rough group of friends,

Billy was regarded as quiet and done assuming.

He kept to himself at school and didn't cause trouble. Recognizing that Billy was another vulnerable teen in need of positive guidance, Pamela also took him under her wing. He helps her with tasks around the school and began regularly visiting her office to assist with a administrative work. With the video competition underway, Pamela helped the students brainstorm ideas and to choose a concept. They met after school a few times each week and on Saturdays to work on the project.

“Whenever they started losing interest, Pamela encouraged to them and helped them stay on track until they completed the video.”

She drove them to filming locations and even agreed to appear in a scene as a cavewoman. She raised eyebrows when she changed into her costume, a leopard print outfit described as "skimpy". Billy recorded Pamela as she pretended to gather wood and wash clothes in a stream. The finished video ran for approximately two to half minutes. It didn't win any prizes.

By this point, Pamela had developed a close friendship with Billy Flynn, who had started visiting her office on a regular basis, often by himself. Pamela encouraged to the visits and provided Billy with passes that excused him from class. On one occasion, Billy mentioned that a neighbor of his own defoto development store and he could obtain discounted rates. Pamela gave him several roles of undeveloped film and asked him to have the process. The resulting photographs showed Pamela posing seductively on a bed in a bikini.

When Billy returned to the photos, Pamela commented that she was unhappy with him. She said she intended to throw them away before suggesting that Billy keep them instead. After this, Pamela asked Cecilia Piest to come to her office. During a private conversation, Pamela told Cecilia that she believed she had developed romantic feelings for 15-year-old Billy Flynn. Cecilia thought it was a joke, but Pamela insisted that she was serious.

She asked Cecilia to bring Billy to her office so that she could speak with him. When Billy arrived, Pamela struggled to tell him what she wanted to say. The following day, Pamela still appeared nervous and reluctant to discuss the matter.

When Billy pressed her for an explanation, she finally revealed to him that she thought about him frequently and was struggling with her feelings because she was married.

Stunned, Billy went back to class. Things were awkward for a period afterwards, but Pamela continued to meet with Billy regularly. Their conversations became increasingly focused on Pamela's marriage, which she described as unhappy. She stated that she had married Gregory largely because many of their friends were getting married at the time. She would call Gregory and deliberately provoke him into arguments, putting him on speakerphone so Billy could secretly listen to their heated exchanges.

She described multiple instances in which Gregory was reportedly unkind to her.

“Billy had no independent way of verifying these claims.”

However, because he trusted Pamela and had developed a close relationship with her, he largely accepted what she told him. He came to feel sorry for Pamela while growing to hate her husband. It was around this time that Billy began reflecting on comments Pamela had made to him in the past. She had once asked whether he knew anyone she could hire to kill her secretary so that a friend could take the woman's job. The question had seemed so blunt and implausible that Billy assumed it was a joke.

But after Pamela confessed her feelings for him, she admitted that her earlier remarks hadn't been entirely made in jest. Pamela told Billy that she didn't actually want her secretary harmed.

“Instead, the person she wished would dead, was her husband, Gregory.”

Even after hearing this, Billy didn't believe Pamela was seriously proposing that anyone should be killed. He interpreted the comments as expressions of frustration and anger rather than genuine intentions. Pamela continued to raise the subject with Billy. She said she wanted to be with him rather than Gregory, but divorce wasn't a viable option. She said Gregory wouldn't willingly let the marriage end, and would make it difficult for her to move on with her life.

She also expressed concerns about the financial consequences of a divorce. Pamela claimed that Gregory would end up with most of their possessions, including their dog, while she would be left with very little.

“She said her salary wasn't enough to afford an apartment, and that she didn't want to move back in with her parents.”

She told Billy that she envisioned the two of them living together somewhere along the coast. To Billy, Pamela seemed like a decent person, even if her comments about Gregory confused him. He told her he didn't know anyone who could be hired to kill her husband, and presumed that would be the end of the discussion. Pamela then began making her relationship with Billy increasingly personal, and spending more time with him outside of school. She even visited Billy at his house when no one else was home.

In his room, she lay on his bed and asked if he was going to kiss her. When Billy didn't act, Pamela asked, "Do I have to come over there and rape you?" She proceeded to sexually assault him.

Billy told several of his friends about what Pamela did, but they didn't believe him at first.

It wasn't until they witnessed her kissing him goodbye after dropping him off, that they realised he was telling the truth. Even then, they struggled to understand the situation. They found it difficult to comprehend why a 22-year-old married woman would pursue a relationship with a 15-year-old high school boy. Billy wasn't the type of teenager who looked older, acted more mature or seemed wiser than he's years. Some suspected that Pamela must have had ulterior motives.

On Valentine's Day, in 1990, while Gregory was away on a ski trip, Pamela invited Billy to spend the evening at her home. She also invited Cecilia Pierce in order to avoid drawing attention to the fact that she was spending time alone with an underage student. Cecilia had also heard of Pamela's complaints about Gregory and their marriage. Pamela went so far as to tell her that she saw only two ways to resolve the situation, divorce Gregory or kill him. When Cecilia suggested that divorce was the better option, Pamela wasn't convinced.

As she had with Billy, she argued that Gregory would end up with most of their assets while she would be left with barely anything. Later that evening, after watching an inappropriate movie with the two teenagers, Pamela took Billy upstairs to her bedroom and raped him multiple times.

She drove the teens home the next day, dropping Cecilia off first.

She lamented to Billy that it might be the last time they saw each other in this way because Gregory didn't go away often.

By the time they arrived at Billy's house, he was sobbing.

He said he felt the same way about Pamela and wanted their relationship to continue. Pamela repeated that she felt she had no option.

“The only way they could be together was if Gregory was dead.”

Over the following weeks, Pamela continued arranging opportunities to meet with Billy and private to assault him. She occasionally told Cecilia about these meetings, but was otherwise careful to keep the elicit relationship hidden from the other people in her life. One time, Billy was a passenger in Pamela's car when it was struck from behind by another vehicle that left the scene.

When completing the accident report, Pamela was required to identify everyone who had been in the vehicle at the time.

She intentionally left out Billy's name. Billy was far less discreet. He boasted to many of his friends about his illicit relationship with Pamela, having been so thoroughly manipulated that he failed to fully grasp that what she was doing to him was a moral, unethical and illegal.

“Still thinking the situation was too absurd to be true, Billy's friends continued to believe he was exaggerating or joking,”

even after he showed them sexually explicit letters she had written to him. One friend asked Billy if he was in love with Pamela.

He replied that he wasn't sure.

And that old acquaintance noticed Billy was in a particularly good mood one day and asked why. Billy replied that he was dating an older woman. When asked how old she was, he revealed that she was 22. That's not old Billy, the man replied casually, to which Billy responded. It's old when you're 15.

“For Billy's 16th birthday, Pamela gifted him a subscription to a music magazine.”

She had intended to buy him a gold bracelet, but decided against it because she feared Gregory would question the $500 purchase. Despite Pamela's desire to keep her elicit relationship hidden, she brazenly had Billy visit her office at work almost every day and to kept his letters professing his love for her in her desk. In addition to Pamela regularly driving Billy around, they went out for lunch together, she bought him alcohol and occasionally hung out with him and his friends.

Privately, they still questioned why she wanted to pursue a relationship with a teenager, especially the meat and ordinary Billy Flynn. Throughout this period, Pamela continued discussing Gregory's death and repeatedly raised the possibility of Billy killing him. She proposed making the crime appear to be a burglary gone wrong. Her plan called for Billy to wear dark clothing, park away from the condominium and approach on foot. He would then enter through an unlocked rear door and wait inside for Gregory to return home before shooting him.

She instructed Billy to wear gloves to avoid leaving fingerprints and to ransack the apartment, saying he could keep any items of value. Pamela said she would establish an alibi by attending a school board meeting. Cecilia Pierce was also present for many of these discussions, although Pamela didn't assign her a direct role in the crime. Pamela would pull the two teens out of class just to plot the murder. She went into considerable detail about how the plan would be carried out, including locking her dog in the cellar to prevent it making noise.

To Cecilia, it didn't seem likely that the murder would actually take place, largely because she knew Billy wasn't a violent person. She even told Pamela that she didn't think Billy would ever go through with it. Pamela nevertheless persisted and eventually began asking the teens if they knew anyone who owned a gun. Cecilia named an acquaintance who kept one in her car. Billy broke into the vehicle on two separate occasions, but didn't find the weapon. Towards the end of March 1990, Pamela surprised Billy by announcing that she wanted the murder to take place that very night.

She said she felt ready, noting that she had a board meeting, and that Gregory was expected home around 9pm.

Billy agreed, but mentioned that he still didn't have a gun, a driver's license, or a car.

Pamela urged him to obtain what was needed by that evening. Billy responded that he would try, but he didn't actually make any attempt to carry out any part of the plan. He was reluctant to proceed and believed Pamela wouldn't react all that strongly if he didn't. He called her after the great time, and she was disappointed to learn that he hadn't followed through. Billy apologized to explaining that he had been unable to obtain a gun or a car.

Pamela's typically gentle, melancholic, and loving tone changed at this point.

“For the first time ever, she got angry at Billy. She accused him of not loving her, while maintaining that killing Gregory was the only way they could be together.”

Before hanging up, she snapped at him. It's over between us. After the call, a heartbroken Billy avoided Pamela, fully believing their relationship was over. However, Pamela instructed Cecilia Pierce to bring Billy to her so she could speak with him. She apologized for her earlier reaction, and told him not to worry, explaining that she had another board meeting scheduled for the following month,

and that he could kill Gregory then.

“Recognizing he was being given a second chance, and fearing Pamela would end their relationship for good if he failed her again,”

Billy resolved to take the plan more seriously. He approached two of his close friends, Patrick Randall and Vince Latamy Jr., and attempted to persuade them to take part in the murder. Billy told the pair that they could keep any items they took from the smart unit, and that Pamela would also give them access to a new car she intended to purchase afterwards, as well as Gregory's pick-up truck and four wheeler. Both boys declined Billy's offer, saying they wanted no involvement.

Billy then spoke to an order acquaintance from his neighborhood.

“18-year-old Raymond Fowler was a high school dropout with a history of minor criminality related to motor vehicle offenses.”

He had recently been released from county jail after a four-month stint for receiving stolen property and conspiracy to receive stolen property. Billy told him the murder would be straightforward because the victim's wife was in on it. He also offered him the opportunity to keep any items stolen from the unit, as well as a further $1,000 Pamela was willing to pay to ensure the murder went ahead. Raymond agreed to participate, but on one condition. He thought Billy would be easily linked to the crime due to his relationship with Pamela.

He requested that Billy merely get him to the condo and act as a lookout. Raymond intended to carry out the murder by himself. Raymond's late father had owned a handgun, but the teens were unable to find it, unaware that it was stored at an uncle's home for safekeeping. They discussed the possibility of using a knife to slit Gregory's throat instead, but the lack of transportation remained an issue.

Pamela ultimately agreed to provide the pair access to her car.

She said she would leave it behind her office building with the keys in the ignition so it could be taken and later returned while she was at the meeting. That night, Pamela arrived at the school. As planned, she left her car parked behind her office building with the keys in the ignition. Billy and Raymond drove the car to Billy's house first to collect a duffel bag with the change of clothes, old shoes, and a knife. Then they stopped at a pharmacy to purchase some latex surgical gloves. As they continued on toward a misty morning drive, the realization of what they were about to do dawned on Billy and he began having second thoughts.

Instead of directing Raymond to Pamela's condominium, Billy claimed that he was lost, hoping it would bring the plan to a swift end. Instead, Raymond stopped at a gas station and asked for directions, putting them back on course.

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Thank you for listening to this episode's ad. By supporting our sponsors, you support Case File to continue to deliver quality content. It was nearing 10pm when the pair reached the condo. Gregory's pickup was parked out the front and the upstairs bedroom light was on, confirming he was inside. This went against the plan where in Billy and Raymond would break into the house before Gregory arrived and lie in wait.

Billy called Pamela from a payphone. By then, the school board meeting was over and she was hiding in her office waiting to hear from them.

“Billy informed her that they couldn't carry out the murder because Gregory was already home.”

Pamela ordered the teens to hurry back to her office. When they got there, she wanted to know what went wrong. Billy remarked that they had gotten lost on the way to laying their arrival long enough for Gregory to reach the condo before they did. Pamela was incredulous as Billy had been to her unit before. She then asked to see the gun they were going to use in the crime.

Billy admitted that they couldn't find one and showed her the knife instead. She chastised them saying in knife would have been far too messy. Raymond tried to placate her saying it would have been less noisy, but Pamela remained unimpressed.

She drove the boy's home, dropping Raymond off first.

Once he was out of the car, Pamela's angry side returned, and she snapped at Billy. You knew the way, you got lost on purpose. If you loved me, you would do this because you would want to be with me. Upset that he had angered Pamela again, Billy assured her that he loved her. She questioned his commitment saying she would end things then and there if he told her he didn't want to do the murder.

Devastated, Billy replied, "No, I'll do it." Pamela told him of another school board meeting scheduled for Tuesday, May 1.

“You have to do it then, she warned, adding that it was the last meeting of the year.”

If he didn't do it that night, that's it, she said. It was around this time that Gregory Smart began to suspect there were serious problems in his marriage. He told friends that Pamela had become increasingly distant, often failing to return his messages, not being where she said she was going to be, and coming home late without explanation. One night, when Pamela said she would be working late, Gregory drove to her office with a friend and observed that her car wasn't in the parking lot.

About 20 minutes later, Pamela arrived alone. When Gregory confronted her about where she had been, she was surprised to see him. Pamela became defensive, accusing Gregory of checking up on her, and deciding that he didn't need to know her movements as she didn't know he is. During a trip to Atlantic City in April with friends and family, Gregory appeared noticeably with the drone. When asked what was wrong, he admitted things were screwed up between him and Pamela.

He had confessed to Pamela that he had a one night stand, but he suspected she had also been unfaithful, even though she wouldn't admit it. In another conversation around this time, Gregory said that he would likely be divorced by the summer.

Meanwhile, Billy Flynn continued planning his second serious attempt on Gregory's life.

“He eventually earned the support of his friends Patrick Randall and Vance Vladimir Jr., despite their earlier refusals to be involved.”

Although Patrick and Vance had previously dismissed Billy's plan, Raymond Fowler's participation convinced them that it was real. Patrick later said he got involved out of concern that Billy might get caught if he didn't have others helping him. He also wanted to make sure Gregory was killed the right way.

Vance II was motivated by a sense of loyalty to Billy and desire to help him, but he later claimed that he was never fully convinced the plan would actually come to fruition.

Still, he and Patrick demanded a payment, and Billy assured them that Pamela was willing to give them $1,000 each from Gregory's life insurance payout. Billy Raymond Patrick and Vance met on at least 20 separate occasions to discuss the murder and several issues they faced. They still lacked both a car and a gun, and there was another problem.

“Too many people knew something was going on.”

In addition to the four conspirators, Cecilia Pierce was aware of the plan, and several of the boys' friends had also been told veering amounts about it. Separately, at least a dozen students also knew about Pamela's illicit relationship with Billy.

Despite this risk, the boys persevered.

Eventually, Vance, the only one with the driver's license, was able to secure access to his grandmother's car. The murder weapon remained a hotly debated topic. Patrick had decided to stab Gregory, but Vance was able to obtain his father's revolver as backup. As Pamela's plan was coming closer to fruition, she made sure to keep the teens on side. While Gregory was away, she had Cecilia and Billy stay over, at one point taking them to the cinema.

When they got back to her unit, she raped Billy again.

“She then took the pair on a drive, pointing out key areas Billy needed to be aware of when he killed Gregory,”

including the grassy hill that would lead him away from the crime scene without being sighted. During the day on Tuesday, May 1, Pamela met with Billy Flynn, Patrick Randall, and Vance Latamy Jr. She informed them that she had left her unit's rear door and a bulkhead to the cellar unlocked and told them where they could find jury they could keep as a reward. She also warned them not to turn on any lights before Gregory arrived home, describing him as a whim who would become suspicious if anything seemed out of place.

The teenagers showed Pamela the gun they had obtained, although Patrick wanted to know whether he could use a knife instead. Irritated, Pamela urged them to use the gun to avoid creating a mess. Billy assured her they would. Pamela also asked the group how she should react when she returned home and discovered Gregory's body. She wondered whether she should scream.

The boys advised her to just behave as naturally as possible. Later that day, Billy, Patrick and Vance picked up Raymond Feller. It was still daylight when they arrived near Misty Morning Drive, so they spent time at a nearby shopping plaza waiting for darkness. Once the sun began to set, each of the boys changed into dark clothing and wrapped tape around their fingertips. Billy slipped the handgun in his jacket pocket.

Raymond and Vance remained by the car, as Billy and Patrick snuck to the condominium and entered through the cellar bulkhead. Gregory wasn't home yet, so the pair began staging the burglary. They used pillowcases to carry the jewelry Pamela had told them to take. Despite her many objections, Patrick retrieved a knife from the kitchen, while Billy prepped the rear door to facilitate their escape. Concerned about leaving fingerprints, Patrick wrapped both his hands and the knife in paper towels.

The pair then waited.

Gregory's pick-up truck finally pulled up, and the boys listened as he approached the front door, unlocked it, and dented.

Billy confronted Gregory first, punching him and forcing him against the wall as Patrick closed the front door and turned off the light.

“After taking a beating, Gregory was ordered unto his knees at knife point.”

He complied, pleading with the teens not to hurt him and asking what they wanted. Patrick told him to be quiet, but Gregory remained concerned about his dog. The boys assured him that the dog was unharmed. Meantaining the appearance of a burglary, they demanded that Gregory hand over his wedding ring. He refused, saying his wife would kill him if he did, but willingly surrendered his wallet.

Billy removed the cash inside, which amounted to only a few dollars.

By this point, the situation was unfolding differently than what either Billy or Patrick had anticipated.

“Gregory's compliance, fear, and the genuine concern he had over losing his wedding ring affected them.”

Patrick, who had previously talked about stabbing Gregory, found himself unable to act. He looked toward Billy and adjusted to his jacket pocket. Billy drew the gun, but hesitated. For several moments, me the teenager moved.

Finally, Billy pointed the weapon at Gregory's head and said, "God forgive me before pulling the trigger."

Billy and Patrick immediately fled through the red door and ran up the grassy hill behind the condominium. In their haste, they dropped several items connected to the crime, including the kitchen knife,

“before reaching Raymond and Vance, who were waiting by the getaway car.”

Billy and Patrick told them that Gregory had been killed, and at the four quickly drove away. As they left to the area, Billy remarked that he couldn't believe he had killed someone. The group discarded the clothing they had worn during the crime by throwing it from the moving car. The four teams reacted differently to what had happened. Billy appeared animated and spoke about the sense of power he felt.

Patrick became quiet and irritable while Vance was primarily concerned with successfully getting away. Raymond allowed the others to stay at his house. They cleaned the gun and Vance later returned it to the place where he'd originally found it. Upon examining the jury the teams had taken from the smart unit, they were dismayed to realize it was all imitation gold with a little monetary value. They threw it all into a river.

The group decided to attend school that after the murder, believing their absence, would attract unwanted attention. But because Billy had spoken to so many peers about the plan beforehand, several students approached him to ask whether he had been involved in Gregory's smarts death. He didn't deny it. The teachers unaware of the scheme later informed Billy and Cecilia Pierce that the husband of their favorite teacher had been killed during the night. Both had defamed surprise.

Pamela continued to meet with Billy after the murder. She didn't want to know the details of the crime, but regularly updated him on what she was hearing about the police investigation. As far as she was concerned, they had successfully gotten away with it, as investigators were pursuing leads unrelated to them. Aware that this success depended on Billy and Cecilia remaining loyal to her, Pamela went to considerable lengths to keep them on her side. She continued to reassure Billy that they would eventually be together, and took Cecilia on a shopping spree, buying her anything she wanted.

But tensions soon began to rise among the other teenagers involved when Pamela avoided paying them, despite having promised $1,000 for their participation in the murder. In their annoyance, they began disclosing what they had done to other friends and classmates. But with more and more people learning about the murder, the group came to realise that being caught was no longer a matter of if, but when. Pamela told Billy not to worry, insisting that because they were all juvenile, they wouldn't face serious consequences.

Meanwhile, Cecilia went to her job at a pizza shop, where she told a coworker named Cindy that her friend Pamela's husband had been killed during a break-in. Cindy immediately recalled a conversation her and Cecilia had from about a month earlier.

“Didn't you tell me about a friend who wanted to have her husband killed, she asked?”

Oh shit, Cecilia replied, realizing that she had forgotten telling Cindy about it. I'm sure what to do with the information, Cindy kept it to herself. Weeks later, while at a social gathering, she mentioned to friends that she knew of a woman from Dairy who's husband had allegedly been killed for insurance money. One of the people who overheard the conversation was alarmed. After leaving together, she went home and called the Dairy Police Department anonymously to report what she had been told, leading investigators to begin looking into Cecilia Piers.

“One question, Cecilia denied knowing anything about Gregory Smart's murder.”

She also claimed to be unaware of any illicit relationship between Pamela Smart and Billy Flynn. Investigators noted that Cecilia appeared visibly stressed during the interview, but she refused to disclose what she knew. Privately, she struggled with the decision to cooperate with authorities, knowing that doing so would implicate her friend Billy and the other boys. She also feared being arrested herself and what punishment she might face for her involvement.

After considerable deliberation, she ultimately decided to tell the police everything she knew.

“With Cecilia's full cooperation, investigators attempted to elicit incriminating statements from Pamela Smart through covertly recorded telephone and in-person conversations.”

During these exchanges with Cecilia, Pamela claimed that Billy Flynn was in love with her, but denied having an affair with him. Despite Cecilia having witnessed her relationship firsthand, including one occasion when she inadvertently walked in on Pamela sexually assaulting Billy. Pamela expressed the confidence that she would have been implicated in Gregory's murder, because she was certain Billy wouldn't testify against her, and there was no evidence linking her to the crime.

She insisted that she couldn't be proven to have hired anyone to kill Gregory, because she had never actually paid anyone to do so.

When Cecilia claimed that police had obtained one of the love letters Pamela had written to Billy, she became noticeably quieter, before again denying any knowledge of the murder. She warned Cecilia that if she told police the truth, she could be charged as an accessory and end up in jail for the rest of her life. Pamela described herself as Cecilia's good friend and insisted that sending her to jail would not solve Cecilia's own problems. She maintained that Billy and the other boys were odd enough to make their own decisions, and that she hadn't forced anyone to do anything.

Pamela was confident that even if the boys confessed that no one would take their word that her or Cecilia were involved. By now, Cecilia's view of Pamela had changed dramatically. While Cecilia was facing serious consequences as a result of Pamela's actions, Pamela was primarily concerned with protecting herself. She was willing to deny or distort the truth, even if it meant others would be punished in her place. It was clear she was no longer the kind and caring friend Cecilia had believed her to be.

Cecilia ultimately reached the upsetting conclusion that if she were to die, Pamela would likely be relieved rather than devastated, as it would mean one fewer person who knew the truth.

Pamela was similarly dismissive about the four boys involved in her scheme, telling Cecilia that because they were underage, they would likely serve no more than a year in youth detention before returning to their normal lives. In reality, all four boys were facing serious charges, including first-degree murder and to life imprisonment without parole for Billy Flynn. In exchange for clear agreements that reduced to their charges and potential sentences, Billy Patrick Randall, Vince Latamy Jr., and Raymond Fowler all gave full admissions and agreed to testify for the prosecution in the case against Pamela's smart.

prosecutors ultimately decided not to pursue charges against her because of her full cooperation with the investigation, including her willingness to secretly record her conversations with Pamela's smart.

“Pamela's smart was charged with accomplice to first-degree murder, conspiracy to commit murder and witness tampering after she was recorded attempting to persuade Cecilia Pierce to lie to police.”

Her trial commenced in March 1991, a little under a year after Gregory's murder.

The prosecution's case relied heavily on the testimony of the teenagers Pamela had enlisted to carry out the killing. Prosecutors portrayed them as naive youth, manipulated by Pamela, who they described as an evil woman bent on murder. Billy Flynn was the prosecution's most significant witness. Soft Spoken and sometimes sobbing, he described how Pamela had groomed him before initiating a romantic relationship that escalated into sexual abuse. His testimony showed that Pamela's abuse wasn't driven solely by a sexual interest in Billy, but was also a means of manipulating him into murdering her husband.

Collectively, the testimony of Billy and his friends portrayed Pamela as more than someone who merely knew about the crime,

“but the mastermind who conceived and encouraged the murder.”

The defense dismissed the teenagers' portrayal of themselves as innocent little manipulated boys, as cock and ball. Instead, they painted Billy Flynn as an infatuated and crazed teenager who had become the ringleader of a group of obsessed thrill killers. They argued that Billy, the other teenagers and Cecilia Pierce, had all implicated Pamela simply to, quote, "save their hides." In the defense's view, Pamela didn't make anyone kill her husband, even if she had disgusted. As for the covert recordings, the defense urged the jury to view Pamela's statements in the context of a confused young widow who had been excluded from the police investigation into her husband's death.

Pamela testified in her own defense.

“Although she finally admitted on the stand to her illicit affair with Billy Flynn, she attempted to use it to distance herself from Gregory's murder.”

She claimed that she had ended things with Billy shortly before Gregory's death because she wanted to repair her marriage, and argued that Billy had killed Gregory in response to that rejection. She denied any prior knowledge of or involvement in the murder plot. The prosecution countered this account with the covert recordings investigators that obtained through Cecilia Pierce, in which Pamela expressed that she had no genuine intention of reconciling with or divorcing Gregory.

They also demonstrated her intensive knowledge of the murder plot.

The jury ultimately found Pamela smart, guilty on all charges, and she was sentenced to life imprisonment without the possibility of parole.

Billy Flynn pleaded guilty to second-degree murder and was sentenced to life imprisonment with parole eligibility after 40 years. 12 years of the minimum sentence could be deferred if he maintained good behaviour. Behind bars, he earned his high school diploma, learned the electrical trade, and took part in charity work. He vowed to spend at least 16 years behind bars as many as he did free. After reaching this milestone in 2007, he sought a sentence reduction.

An apology to Gregory's smart family didn't move them as they opposed Billy's request.

It was ultimately denied, but his parole eligibility date was reduced by three to 25 years.

In 2015, on the 25th anniversary of Gregory's smart's murder, Billy Flynn was granted parole and released from prison at age 41. Patrick Randall also pleaded guilty to second-degree murder and received essentially the same sentence as Billy, with 12 years deferred, later reduced by a further three years. He was also paroleed in 2015. Vance led a me junior pleaded guilty as an accomplice to second-degree murder, and was sentenced to life imprisonment with parole eligibility after 30 years.

He was released in 2005.

“Raymond Fowler pleaded guilty to conspiracy to commit murder and attempted burglary. He was sentenced to 30 years imprisonment with parole eligibility after 15 years.”

He was first paroleed in 2003, returned to prison after violating parole, and was released again in 2005. The young man involved in the case have largely kept a low profile since their release, avoiding media attention and making few if any public statements.

Cecilia Pierce broke her silence in a 2016 interview with the New Hampshire magazine, saying she wished she had never met Pamela Smart.

Reflecting on their relationship, Cecilia recalled the many kind things Pamela did for her and Billy, such as cooking them dinner and taking them sledding.

“But now realized those gestures were part of the greater goal she had in mind.”

Cecilia believed that people continued to doubt or dismiss their experiences of her and the other teenagers, because Pamela was perceived as physically attractive. With Billy's case in particular, she highlighted that many people struggled to comprehend that a teenage boy could be the victim of sexual abuse by an older woman whom they considered in their words, to be hot. Cecilia also remembered leaving the courthouse after Pamela's trial while reporters and photographers chased her across the lawn, an experience she found frightening.

The intense media scrutiny ultimately caused her to abandon her dream of becoming a reporter.

“In prison, Pamela Smart maintained her innocence, asserting that Billy Flynn was the only person who could clear her name by telling the truth, adding, "But he's never going to do that."”

Multiple attempts to appeal her conviction were unsuccessful. In June 2024, after serving 33 years in prison, 56-year-old Pamela saw the reduction of her sentence. As part of that effort, she stated that she had engaged in significant self-reflection, and for the first time, accepted responsibility for Gregory's death. "I had to acknowledge for the first time in my own mind and my own heart how responsible I was, because I had deflected blame all the time, I think almost as if it was a coping mechanism, because the truth of being so responsible was very difficult for me."

Pamela's request was rejected, and she remains incarcerated under her original sentence of life imprisonment without the possibility of parole.

The Pamela Smart case had a lasting impact on popular culture and the media, becoming one of the most widely adapted true crime cases of the 1990s. It inspired numerous books, documentaries, true crime programs, a 1991 television movie, and the acclaimed fictionalized 1995 film to die for starring Nicole Kidman. It's influence also extended into mainstream entertainment, with references and parodies appearing in series such as "Laund Order" and "Family Guy." Pamela Smart continues to divide public opinion. To her critics, her repeated attempts to secure a release from prison, his further evidence of her manipulative nature described as "Sociopathic."

Data officials contend that because she hasn't demonstrated genuine accountability or remorse, she should not be granted clemency or compassion. Some supporters maintain that she is completely innocent, while others who accept her influence in the crime argue that she was nevertheless unfairly convicted. Some prominent U.S. feminists have highlighted the disparity in sentencing, noting that the young men who actually committed the murder have all been released from prison, while Pamela remains incarcerated.

When Pamela first arrived at the maximum security women's correctional facility where she continues to serve her life sentence, she was required to surrender her wedding ring because it's diamond setting violated prison regulations. She entrusted the ring to her mother for safekeeping. In an exclusive interview with the Washington Post from prison, Pamela said the ring remained deeply meaningful to her, and that she wished she could keep it. Why wouldn't I, she asked? I mean, I'm still married.