Cold Water: Where is Jennifer, and the Trial of Dean Penney

This episode contains descriptions of domestic violence that some listeners may find disturbing. Please take care of yourself.  

Also, please note that there is no written record of court proceedings available.  All of the information was obtained through news articles.  Unfortunately, news sources don’t report all the facts from court, which means there is likely more information that the jury had available to them then I was able to present here

INTRO

It was a Thursday morning in December. The kind of morning when St. Anthony, Newfoundland,  a fishing village of 2500 people, clinging to the northern tip of the island, is still pitch black at a quarter to seven.

Inside the house at 8 Husky Drive, fifteen-year-old Deana Penney woke to a persistent noise. It was her mother's phone alarm, ringing from the kitchen. She banged on the bedroom door. No answer. She opened it. Nobody inside.

She walked through the house. Her mother's phone was on the counter. Her purse was on the table. Her keys were still in the ignition of her car, parked in the driveway. Her shoes were at the door.

Everything was set down, Deana would later tell a jury, as though her mother had just arrived home and left it all behind.

Deana called her grandmother. Ruby Penney came over within 20 minutes. Ruby called her son, Deana’s father, Dean Penney, who drove in from his hunting cabin right away.

But Jennifer Hillier-Penney was gone. She was thirty-eight years old. A mother of two. And she would never be seen again.

For seven years, nobody was charged. For seven years, her family fought to keep her face in the public eye, plastering posters across town while the RCMP conducted searches over land and sea, coming up with nothing.

And then, in December of 2023, Dean Penney was arrested at the Deer Lake airport. What the public didn't know, what almost nobody knew, was that the RCMP had spent the previous four years running one of the most elaborate undercover operations in Canadian history to get him to talk.

They built an entire criminal empire around him. They gave him a best friend. They took him on heists, diamond runs, and gun deals from Newfoundland to Alberta to British Columbia. They paid him $27,000. And in the end, on a yacht in Vancouver harbour, exactly seven years to the day his wife disappeared, Dean Penney sat across from a man he believed was a mob boss, and told him what happened that night.

Or did he?

That is the question a jury of twelve spent four days deliberating, after an eight-week trial that gripped the province.

I'm your host, Ryan Dell. This is Canadian CrimeCast: Coast to Coast True Crime.

CHAPTER ONE — The Night She Vanished

To understand what happened in that courtroom in Corner Brook, you need to go back to the night it all began.

November 30th, 2016. A Wednesday. Late fall on the Northern Peninsula, where darkness comes by 4:30 in the afternoon and wind cuts through everything.

Jennifer Hillier-Penney and Dean Penney had separated that September after roughly 18 years together. Their marriage was over, and Jennifer wanted a divorce. Just nine days earlier, on November 21st, she'd had a lengthy phone call with a lawyer named Jim Bennett about retaining him for divorce proceedings. They were supposed to meet in December.

That meeting would never happen.

Text messages between the couple, 627 pages of them, spanning from September to November, painted a picture the Crown would later present to the jury. Dean was desperate to get Jennifer back. But the messages also showed his anger at the fact that she could take half of his assets. On the day she disappeared, he texted her about their belongings, telling her he didn't want her taking half his stuff.

Despite the separation, Jennifer had come back to the family home on Husky Dr that night. She was babysitting their youngest daughter, Deana, while Dean was supposed to be 45 minutes away at his cabin in Northwest Arm, hunting ducks.

Earlier that evening, Jennifer's sister, Yvonne, was riding in a car with her. Jennifer got a phone call from Dean. Yvonne would later tell the court that Penney seemed upset, questioning when Jennifer would be returning to the house.

Jennifer dropped her sister off at the hospital in St. Anthony. Then she drove home to Husky Dr.

At 4:47 pm that day, Dean had texted Jennifer: "Is she home yet?”, asking about Deana.

Jennifer replied: "She's fine."

That was the last message Jennifer Hillier-Penney's phone ever sent.

Dean sent four more texts after that. The final one, at 7:17 pm, asking Jennifer to tell Deana to call him when she arrived home safe and sound.

There was never a reply.

What the jury would later learn is that Deana did come home that night, around 9pm. She noticed her mother's phone in the kitchen. She saw the bedroom door was closed. She assumed her mom had fallen asleep.

Then, around 11pm, Deana got a phone call from her father. He said he needed to come grab some hunting decoys from the garage and didn't want to scare her. Deana popped her head into the garage a few minutes later to say goodnight. She saw him pick up broken decoys from the floor, put them into a bag, sling it over his shoulder, and leave.

She thought nothing of it. The house was normal. Untouched.

The next morning, December 1st, 2016, she woke to her mother's phone alarm. She banged on the bedroom door. Found nobody inside. And noticed that everything her mother owned was exactly where she'd left it the night before.

She called her grandmother. Ruby called Dean. And the search began.

But here's a detail that would matter later: when the RCMP arrived and Cst Camille Bryan sat down with Penney at his dining room table, he told her he had no idea where Jennifer could be. He said he'd been at his cabin all day.

What he didn't tell police was that his own daughter had seen him in the garage the night before, after Jennifer was last seen, but before she was reported missing.

CHAPTER TWO — The Shifting Stories

In the days following Jennifer's disappearance, Dean Penney gave three statements to the RCMP. And in each one, his story changed.

In the first statement, on December 1st, he told Constable Bryan he'd been at his cabin and only came to St. Anthony late that evening to get gas. He made no mention of calling Jennifer that night. No mention of going to the house.

Two days later, in a second interview at the RCMP detachment, S/Sgt Daniel Murrin told Penney directly that he was in the suspect pool. Penney didn't flinch. He said he had nothing to hide, that he wanted to find her as bad as anybody. This time, he admitted he had called Jennifer that night and that he'd gone to the house around eleven to collect his duck decoys. He also expressed concern that her disappearance would leave him with a financial burden, since she was still helping with some of the bills.

But it was the third interview, on December 8th, that really rattled things. The RCMP told Penney that an eyewitness had spotted his vehicle driving through St. Anthony at 7:50 pm, the exact time Jennifer was last seen alive.

His response was revealing. He said that if it says it was him, it must have been him. That he definitely could have been in town in the evening. He couldn't remember the time, but if the evidence placed him there, then he was there.

He suggested it must have been a coffee run, a detail he had never mentioned in either of his first two interviews. The drive from the cabin to St. Anthony is about 45 minutes each way.

Three interviews. Three different versions. Each one adding details only after the RCMP confronted him with evidence he couldn't explain away.

From my years in policing, I can tell you this is a pattern investigators see over and over. Guilty people don't usually confess outright. They concede ground inch by inch, only admitting what they think the police already know. And each new admission raises the same question: what else aren't you telling us?

But the RCMP had a problem. They had no body. No forensic evidence. No murder weapon. No witness to any crime. They had a missing woman, a suspicious husband, and a story that kept changing, but nothing they could take to court.

Meanwhile, on the very day Jennifer was reported missing, Dean's mother, Ruby Penney, walked into the RCMP detachment in St. Anthony and gave a voluntary statement. She said there was one thing she couldn't get out of her head, a phone call Jennifer had with her cousin Derick Hillier, seven months earlier. Ruby, Jennifer, and Deana had been coming home from a trip to Florida when Derick, who'd been hospitalized at the Waterford psychiatric facility in St. John's, called Jennifer and told her he was Jesus Christ. He said he was coming to her house with all of her dead relatives to take her to a party in heaven.

Ruby expressed guilt at bringing his name up. He was her friend. But she told the officer it was possible he had done something.

I'll come back to Derick Hillier. Because the defence would build an entire theory around him.

But for now, the RCMP made a decision. They were going to build something that would make Dean Penney talk. Something he would never see coming.

CHAPTER THREE — The Bump

In the world of Canadian policing, there is a controversial investigative technique known as a Mr. Big operation. It has been used in hundreds of cases, mostly homicides, and it works like this: undercover officers create a fictitious criminal organization and befriend the suspect, slowly drawing them into the group. Over weeks, months, sometimes years, they build trust, offer financial incentives, and create an environment where the suspect feels safe sharing secrets. The operation culminates in a meeting with the "boss" of the organization, Mr. Big, during which the suspect is encouraged to confess.

It is a uniquely Canadian invention. It has landed more than a few guilty people behind bars. But it has also produced false confessions, people who told Mr. Big what they thought he wanted to hear, because they were scared, desperate, or simply wanted to belong. The Supreme Court of Canada recognized this risk in a landmark 2014 ruling, and since then, juries have been instructed to carefully scrutinize these confessions.

The RCMP launched their operation against Dean Penney in September of 2019, nearly three years after Jennifer disappeared. They called it Project Brusque. And it would become one of the longest Mr. Big operations on record, spanning 50 months, involving 66 scenarios and a 105 separate engagements with Penney.

The architect of the operation, the man who designed every scenario and played the role of second-in-command, testified behind a black screen at trial. A publication ban protects his identity, along with every other undercover officer involved. In court, they went by pseudonyms: Joe, Vic, Rudy.

It began, as these things always do, with what's called "the bump”, the first casual, seemingly accidental encounter.

Making contact with Penney in a small town where everybody knew everybody was its own challenge. The architect told the court they had to have a reason to be there and a reason to need Penney's help. In a community that small, a stranger asking questions would be noticed within the hour.

But the RCMP had done their homework. They knew Penney was a fisherman, a hunter, and a woodsman. They knew he had a cabin. And they knew he was increasingly isolated. After Jennifer's disappearance, the finger had been pointed at him almost immediately. He testified later that he received death threats. That someone shot a bullet into the back wall of his house. That his friends had abandoned him. He'd turned to cocaine as a coping mechanism, calling it a crutch.

In January of 2020, an undercover officer ran into Penney at the local fish plant. He asked about renting Penney's cabin and hiring him as a guide for a hunting trip. Penney agreed. He took two undercover officers into the woods.

While on the trip, the officers faked an urgent phone call and told Penney they had to fly to St. John's immediately. They asked if he'd drive their truck over 1000 kms south to the capital city. He said yes. Along the way, he was asked to stop in St. Barbe and pick up some thumb drives.

Penney did it without question. He was paid $1000.

And just like that, Dean Penney was inside the organization.

CHAPTER FOUR — Building the World

What followed was an astonishing exercise in deception,  a years-long, cross-country performance involving dozens of RCMP officers playing criminals, corrupt officials, sex workers, military personnel, and bikers.

The undercover team explained to Penney that the thumb drives he'd transported had been stolen from RCMP headquarters by a corrupt officer, and were being sent to a corrupt military contact in Happy Valley-Goose Bay who could decrypt them. The information could be used by the gang or sold to other criminals.

This accomplished several things at once. It showed Penney the sophistication of the organization. It demonstrated that they had contacts inside the police, planting the seed that they could access confidential documents, including anything related to the investigation into his wife's disappearance. And it gave them a plausible reason for being on the Northern Peninsula.

In October 2021, Penney met the fake RCMP contact near headquarters in St. John's. She told him she was disgruntled because the force had denied her leave to care for a sick child. It was all a ruse, designed to make Penney believe the organization could get its hands on police files about him.

The scenarios grew more elaborate over time. Penney travelled to Halifax to conduct surveillance on a fellow "gang member" suspected of drinking on the job. The man was caught and fired, staged to show Penney that people could leave the organization without being harmed. He attended a retirement party for another member.

He participated in what he believed was a fuel heist at the U.S. border crossing in Coutts, Alberta, where the organization supposedly paid off a corrupt border guard with marijuana. He drove to a military base in Wainwright, Alberta, where armed guards in full uniform pushed a crate into their truck. Penney and another undercover officer were told the crate contained firearms. In reality, it was full of pipes and lead bars. But Penney didn't know that, and when the group later unboxed what he was told were 30 Glock handguns in Regina, he joked nervously, asking which one was his, trying to lighten the tension.

He took part in a diamond transfer by train from Ontario to Alberta. The organization threw him a birthday party in Banff and gave him a pair of $300 boots.

Through it all, Penney was paid. $27,200 over the course of the operation.

But the scenarios weren't just about money and action. Each one was designed to show Penney a particular truth about the organization: that it was powerful. That it was connected. That it rewarded loyalty and honesty. And,  critically, that it could make problems disappear.

CHAPTER FIVE — The Best Friend

At the centre of Penney's world inside the organization was a man he knew only as Vic.

Vic was the primary undercover operator, the officer tasked with befriending Penney and becoming the closest person in his life. And by every measure, he succeeded.

They spent countless hours driving around St. Anthony, cooking meals, watching movies, going hunting and fishing. Penney took Vic snowmobiling. He introduced Vic to his youngest daughter, Deana. He later brought Vic to meet his new girlfriend. Penney told Vic he didn't have to knock if he wanted to come by the house, and offered him food and a place to stay whenever he needed it.

They spoke on holidays and exchanged gifts. Penney had a local carver make a soapstone sculpture of a polar bear for Vic, a gift Vic told the court was one of the best he'd ever received. On Penney's birthday in 2023, during a job in Banff, Vic bought Timbits at Tim Hortons and sang Happy Birthday in the truck. He said he probably wasn't very successful as a singer, but he was sure Penney appreciated it.

When Penney's mother, Ruby, died on August 14th, 2021,  a date Vic recalled without any help, Vic was there. He told the court that Penney had lost about 25 pounds since their last meeting and was smoking marijuana frequently. Penney was struggling financially, his mother had left him her cabin, and he was worried about keeping up two homes. The house was getting dirty around him. Beer bottles Vic had seen months earlier were still lying around.

And then, the very next day, Vic and the other officers showed up with job opportunities within the organization. Vic noticed Penney was well groomed and the house was cleaner.

On December 3rd, 2020, Penney and Vic had a conversation that was captured on a recording device Vic was wearing. The court heard Penney tell Vic that he wanted closure. That they had to know he had nothing to do with it. That Jennifer was the mother of his children. That he loved her whether they were together or separated. That he'd never hurt her, and he'd never let anybody else hurt her.

Vic replied by telling Penney that even if he was somehow involved, it wouldn't change their friendship.

When Vic took the stand, something remarkable happened. He spoke fondly of Penney. He told the court he wished for a different outcome. That Penney was not seated in the place he wanted him to be, but that's just not the way things worked out. That if he hadn't been sitting in a courtroom with a jury and counsel, he would have been quite happy.

In my years of policing, I've seen undercover operations up close. The officers who do this work are trained to build trust, it’s the job. But what struck me about Vic's testimony is how the line between the mission and the man had blurred. He wasn't performing when he said those things. He meant them. And that complexity, the idea that a friendship can be both manufactured and genuine at the same time, is something the jury had to wrestle with.

But there was another layer to the friendship, a darker one, carefully engineered by the architect.

In 2022, Vic made a fake confession to Penney. They were at a restaurant in Regina when a man confronted their table. Vic became sullen and withdrawn. The next day, on a long drive, he opened up. He told Penney that years earlier, he had gone to collect a debt in Saskatchewan. Another man showed up with a knife. After a brief struggle, Vic said he stabbed the man to death. He gave Penney the name of a real person, whose 2013 murder remains unsolved.

The disclosure was emotional. Penney was supportive and consoling, insisting Vic had only acted in self-defence. He told Vic he would always have his back.

The purpose, according to the architect, was to show Penney that the organization would protect you if you told the truth. That they had the power to create alibis, backdate records, and make problems go away. The man told Penney the organization had sent him to a Mexican rehab facility and backdated his trip so it looked like he had an alibi for the time of the killing.

But the defence would argue the scenario accomplished something far more sinister. It showed Penney that these were people who killed. And if a man who murdered someone could be embraced and protected by the organization, what would happen to someone who tried to leave, or someone who knew too much?

CHAPTER SIX — Violence Against Women

As the operation progressed, the RCMP introduced the element of violence, specifically, violence against women.

Penney had told Vic on multiple occasions that he was against violence against women. That he was raised better than that. The undercover team needed to dismantle that boundary. As Vic explained to the court, if Penney had been involved in a crime against a woman, this scenario would help lay the foundation for him to talk about it.

In November 2022, Penney travelled to Calgary to pick up another undercover officer, a man using the pseudonym Dinger, who was supposedly just out of prison for aggravated assault after attacking his girlfriend and stabbing her lover. The organization threw Dinger a party in Edmonton. The next morning, Dinger was missing. When he turned up, he told the group he'd gone home with a woman and attacked her. He didn't know if she was dead or alive.

Penney was thrust into the middle of it. The group scrambled to create an alibi, driving to a casino on a reservation where a member's cousin could supposedly alter security footage timestamps. Penney even suggested that Dinger ditch his clothes, since there could be evidence on them.

Later, the group confronted the woman, an undercover officer named Judith, and her supposed pimp at a motel, demanding the debt be wiped clean in exchange for her silence. Audio recordings played in court captured Penney yelling at the woman he believed was a beaten sex worker.

Vic told the court that Penney didn't seem fazed by any of it. He didn't seem intimidated.

And in November 2023, just before the final act, Penney asked Vic a question that would echo through the courtroom. He asked whether the organization had ever had to get rid of anyone. Whether there were consequences for someone who knew too much.

Vic paused. Then he said: "No, not really, no. If you ever did something stupid, then maybe that's something different."

Defence lawyer Mark Gruchy seized on those two words, "not really”,  arguing that Vic had opened the door to the idea that violence could happen to someone who crossed the organization. Vic pushed back, saying the organization used leverage over violence, and that they'd never portrayed themselves as people who harmed their own.

Gruchy compared the crime boss to Al Capone.

Vic was quick to respond. "Except for, uh, we don't whack people. We don't whack each other."

The foundation was set. The final act was about to begin.

CHAPTER SEVEN — The Yacht

In late November 2023, the operation reached its culmination. Penney was told there was a job opening, as captain of the crime boss's yacht, based in Vancouver. It was the kind of opportunity that would change everything for a man who was, by this point, financially desperate. His family had sold their offshore fishing licence. He'd barely made five thousand dollars fishing in 2023, not enough to qualify for employment insurance. The day before his interview, the roof had blown off his family home. He was considering bankruptcy.

Penney flew from Deer Lake to Vancouver. He spent a day working on the yacht, cooking for the crew. And then, on November 30th, 2023, exactly seven years to the day his wife disappeared, he sat down for what he believed was a job interview with the crime boss.

The man across from him was an undercover RCMP officer using the pseudonym Rudy. A veteran who had played the role of a crime boss more than a dozen times over nearly 25 years of policing.

The conversation lasted over four hours. It was secretly recorded.

Rudy began by lecturing Penney about honesty. He told Penney the members of the organization were like family, and that he had the rare opportunity to choose his family. He said he had to talk about mistakes and how they're handled.

Penney told Rudy he would give him a hundred and fifty percent honesty. He said the job would be a game changer for him, describing his compounding financial stresses.

For the first portion of the interview, Penney insisted he had nothing to do with Jennifer's disappearance. He told Rudy, plainly and directly, that he had nothing to do with it. That he had absolutely nothing to do with it.

But Rudy was patient. And he had a tool.

He presented Penney with a document, a fake RCMP memo that Rudy had created himself. It said the police were close to arresting Penney for Jennifer's murder. It said a comprehensive press conference had already been planned that would garner national and international interest. It said officers should be prepared.

The memo was a lie. Every detail about an imminent arrest was fabricated. But Penney didn't know that. He read the document on board the yacht and told the court it upset him, that he knew in his heart he had nothing to do with it, but the document was designed to make him feel guilty.

Penney questioned whether the police were going to come storming in with handcuffs if he started talking. Rudy's voice rose at the suggestion, challenging him to take it back.

And then, approximately twenty-six minutes after his final plea of innocence, and nearly three hours into the conversation, Penney's story changed.

He told Rudy the night started with an argument. He said he'd come to the house to grab his duck decoys while Jennifer was sleeping, but a door opening woke her. She was agitated. They argued in the laundry room, which connected to the garage via a small staircase.

He pushed her. She fell down the stairs and hit her head on his gun safe.

He said she didn't have a pulse. Blood was coming from her head and ears. He cleaned the garage with bleach. He wrapped her in plastic wrap and garbage bags, put her into his duck decoy bag. He loaded her into his vehicle, drove to his cabin, put her body into his twelve-foot fishing boat, and motored out into Hare Bay in the darkness. He filled a satchel with rocks to make sure she sank. He threw everything overboard and watched it sink.

He told Rudy he could give him the exact latitude and longitude. That he knew the charts. That he knew exactly where he put her. That she would never be seen.

During a break in the conversation, Penney sat with his hands over his eyes. He said he'd been holding it for so long. That it was kind of a relief.

The interview ended with other members of the organization, all undercover police officers, entering the room and celebrating with Penney after learning he was in line to become the yacht's next captain.

CHAPTER EIGHT — The Second Interview

Eight days later, on December 8th, 2023, Rudy brought Penney back for a second conversation at a covert location in Edmonton.

Penney wasn't expecting it. He thought they were finalizing his contract for the captain's job. But Rudy told him there were things about his story that didn't add up. That his second-in-command didn't believe someone could take a tumble like Penney described and die from it.

This time, the story changed, and in a critical way.

After Jennifer fell down the stairs, Penney said, he picked up a small mallet hammer that was sitting on the floor and hit her in the head. Two, maybe three times. Hard enough that the third blow caused what he described as a big splatter.

Penney and Rudy re-enacted the incident, with Rudy simulating Jennifer's position while Penney demonstrated the blows.

The courtroom fell silent as that video was played. Members of Jennifer's family, who had been present every single day of the trial, sobbed audibly. Some of her cousins, attending for the first time, held each other in the front row. Jurors wiped away tears. Penney kept his head down, following along with a transcript.

He provided new details about disposing the body. He said he drove to the cabin in the dark with his lights off, rolling down to the wharf as quietly and discreetly as possible. He used boards installed on the boat, meant for holding duck decoys, as a ramp to roll the body into the water. He placed weight around Jennifer's ankles and feet to ensure she sank.

He also gave Rudy the location on a map using mapping software. Rudy pulled a weather report from the night, showing wind gusts over thirty-five kilometres per hour during Penney's ride across the water.

One week later, on December 15th, 2023, Dean Penney landed at the Deer Lake airport. He was taken into custody. The RCMP had kept him busy with non-criminal maintenance jobs in Edmonton for those final days, buying time while investigators in Newfoundland prepared for his arrest.

CHAPTER NINE — The Trial

The trial began on April 1st, 2026, in the Supreme Court of Newfoundland and Labrador in Corner Brook. It was presided over by Justice Vikas Khaladkar. Crown attorneys Shawn Patten and Kate Ashton prosecuted. Defence lawyers Mark Gruchy and Jeff Brace, both veterans from the province's legal aid commission, represented Penney.

From the outset, the trial was marked by disruptions. On the very first Thursday, proceedings were shut down because there weren't enough sheriff's officers to bring Penney to court. Justice Khaladkar was furious. He directed his comments at the media, calling the situation deplorable, saying a man was facing life in prison and this wasn't a speeding ticket. He even rejected a suggestion that Penney appear by video from the lockup. There were further delays from problems with the court's audio recording system and legal issues with evidence.

But when the trial was running, it was riveting.

The Crown called twenty-two witnesses. The jury heard Penney's three police interviews, each with its shifting details. They heard from Jennifer's sister, who described the phone call the night of the disappearance. They heard from Deana, who described waking to her mother's alarm and finding the house untouched. They heard from a cell tower expert who placed Penney in St. Anthony for four hours on the evening of November 30th, between 6:00 and 10:30 at night, contradicting his original claim that he was at his cabin all day.

They heard from Morley Hillier, who is of no relation to Jennifer, but a man who grew up next door to her family. He told the court he'd run into Dean in a Scotiabank parking lot in early November 2016. He said Dean told him about the separation and made a chilling remark: that Jennifer was going to disappear, and the Hilliers weren't going to get anything he worked for.

Under cross-examination, Gruchy hammered Hillier on his heavy drinking, his troubled relationship with Dean, which included an incident where Penney punched him in the face, and the fact that he'd previously told police the encounter happened in Clarenville, not St. Anthony.

And then came the text messages. 627 pages of them, printed in binders and placed at tables in the centre of the courtroom. The jury sat around those tables and read them in silence, with Penney required to be present for the entire process. It took over a day. Those messages showed a man desperate to save his marriage,  and furious at what he stood to lose. The last text exchange was the one I described earlier: Dean asking if Deana was home yet, Jennifer replying "She's fine," and then silence.

The jury heard from forensic specialists who found presumed blood stains in Penney's garage in 2023, seven years after the alleged murder. The stains glowed blue under chemical testing, indicating the possible presence of iron found in hemoglobin. They were found between the stairs and Penney's gun safe, exactly where his confession said Jennifer had fallen.

But the defence scored points here. Lab testing could not confirm the stains were blood. False positives can come from bleach, mold, leather, even turnip. DNA testing found Jennifer's DNA on the garage wall, nearly three metres off the floor,  but the defence argued this wasn't surprising, since she lived in the house. And the DNA found on the stained areas near the stairs belonged to neither Dean nor Jennifer.

And then there was the ocean. Six diving missions over a year and a half. 135 anomalies scoured with sonar, remote-operated vehicles, and support from the Royal Canadian Navy. They searched the exact coordinates Penney had given the crime boss.

They found nothing.

No body. No duck decoy bag. No Sea-Doo cover. No rubber boots full of rocks. No mallet. Defence lawyer Jeff Brace put it directly to the RCMP diver: in ideal conditions, they would have found the body. And there were no rubber boots full of rocks, no Sea-Doo covers, no decoy bags. And certainly no sign that Jennifer Hillier-Penney was ever there.

An acoustics expert from Memorial University testified that finding a body wrapped in canvas and plastic after that much time would have been extraordinarily difficult. He said you'd have to be lucky and in the right place, that things would have to line up very nicely.

In no-body cases the absence of remains is always the defence's strongest card. It creates a shadow of doubt that hangs over everything else. The Crown has to convince a jury that someone is dead without being able to show them a body. And the defence gets to ask a simple question that's hard to shake: if the confession is true, where is she?

CHAPTER TEN — The Daughters

Two moments from the trial deserve to stand on their own, because they show what this case did to the people closest to it.

The first came when Marina Goodyear, the eldest daughter of Dean and Jennifer, took the witness stand. Their time in the courtroom together was brief, but it was enough for Marina to shoot glares from the witness box toward her father, who was sitting in the prisoner's box surrounded by sheriff's officers.

The Crown asked her to identify anyone she knew in CCTV footage from the Irving gas station in St. Anthony on the night of November 30th, 2016. There was a long period of silence as the footage played. Then Penney appeared on screen.

"That was my dad," she said.

Penney had told the crime boss he stopped at the gas station around 10:45 pm,  partly to fuel up, but also because he knew the station had surveillance cameras and wanted to be placed there on the record. He told Rudy it was to make it look good.

Marina told the court that her mother had told her she was scared of Dean. She wouldn't say why. Just that she was scared.

Under cross-examination, defence lawyer Jeff Brace pointed to police statements Marina had made in January 2017, in which she'd identified other family members and friends police should look into, including Derick Hillier.

Marina snapped back. She said that when she went to St. Anthony after her mother went missing, she went back to the house on Husky Drive and was probably experiencing some brainwashing by her father and by her grandmother. The only reason Derick Hillier was ever in her made-up suspect list, she said, was because of them.

CHAPTER ELEVEN — The Alternate Suspect

That brings us to Derick Hillier, the man the defence built an entire theory around.

Derick was Jennifer's cousin. He struggled with bipolar disorder, made worse by a cocaine addiction. He had been in and out of the Waterford psychiatric hospital for about eight months before Jennifer's disappearance.

Multiple witnesses testified about the phone call from the hospital, the one where Derick told Jennifer he was Jesus Christ, coming to take her to a party in heaven with her dead relatives. Dean's mother Ruby raised it the day Jennifer was reported missing. Deana heard the call. It clearly disturbed people who knew about it.

But the defence went further. They presented evidence that Derick had a documented history of violence. In January 2003, he was charged with uttering threats toward a woman named Louise Hedderson. While holding a knife, he spoke about another woman who had vanished from St. Anthony, Mildred Dawe Sexton, who disappeared in April 2002 and was never found.

His words, read from a statement in the courtroom, were chilling: if you open your mouth about anything, then you'll disappear like Mildred did.

He was convicted of uttering threats, assault, and mischief. During his arrest, he threatened to kill a police officer with his bare hands, telling the officer he was an easy body to get rid of.

Both Hedderson and Derick Hillier are now dead. Neither can provide further testimony or defend themselves.

Derick's parents testified that he left St. Anthony on the morning of November 30th, 2016, and drove across the island. His mother, Norma, said she met him in a Tim Hortons parking lot in Gander, about 700 kms away, that afternoon.

But the defence poked a significant hole in that alibi. In a statement to the RCMP in February 2017, Norma told investigators she discussed Jennifer's disappearance with Derick during that very same meeting. She also said she ran into friends from St. Anthony in the parking lot who discussed it too.

The problem: Jennifer wasn't reported missing until the following day. If Norma really did discuss the disappearance at that meeting, it happened on December 1st,  meaning Derick could have still been in St. Anthony on the night Jennifer vanished.

Norma said she made a mistake. That she mixed up a phone conversation with an in-person meeting.

The courtroom exchange was tense. Norma pushed back against the line of questioning, saying it felt like she was the one on trial. And then she did something that brought proceedings to a sharp halt, she turned her gaze directly to Penney in the prisoner's box and urged him to look her in the eyes.

Justice Khaladkar slammed his hands down on the bench. He told her to stop. That she had been told to answer the questions. That she could not do that.

The jury also heard a recording of a thirteen-minute RCMP interview with Derick himself, from December 19th, 2016. He confirmed he left St. Anthony on November 30th, around seven in the morning. He said he'd called Jennifer once while he was back in town but she told him she was at the mall and would call back. She never did.

The Crown argued there was no evidence Derick Hillier could have committed the crime, and that the evidence showed he wasn't even in town that day. The defence argued the RCMP never adequately investigated him, never checked his bank records, never pulled gas station CCTV footage, never took his DNA or fingerprints.

CHAPTER TWELVE — The Accused Takes the Stand

On May 7th, 2026, Dean Penney made the short walk from the prisoner's box to the witness box. It was a rare move in a first-degree murder trial, and it opened him up to cross-examination by the Crown.

Over the course of five days, Penney told the jury his version of events. He spoke about his life as a fisherman, the family business, the house he built with Jennifer. He said he loved her very much. He said he struggled to understand why his marriage was falling apart. He worked hard to put things back together, but they drifted apart.

He spoke about the undercover operation, how Vic became one of his best friends, how the money was desperately needed, how the scenarios made him increasingly uneasy. He described the organization as very big and very powerful, with muscle in a lot of places and connections everywhere. It was the kind of thing you'd see on TV, he said. You don't see much like that when you're fishing.

He told the jury he was scared. That Vic's confession about killing a man in Saskatchewan was about the most stressful thing he'd gone through with the group. That the guns and the violence and the organization's reach made him feel like he couldn't leave, because he knew too much.

And then he told the jury what happened on the yacht.

He said Rudy wasn't interested in hearing that Penney was innocent. That the crime boss kept cutting him off, steering him toward a confession. That the fake RCMP memo upset him deeply. He said he knew in his heart he had nothing to do with Jennifer's disappearance, but Rudy wouldn't accept that.

He said he didn't think he was going to be allowed to leave. That even though Rudy told him he could go, Penney felt that knowing what he knew about the organization, leaving could put his life in jeopardy. He said Rudy was getting more and more agitated,  something he said couldn't be seen on the video played for the jury because Rudy's face was blurred.

He said all that was really going through his mind was how to make up a story that would sound like it could be true. He told them he gave Rudy the story the community had been throwing at him for seven years, that he killed his wife and dumped her in the ocean. It wasn't hard to come up with, he said. It was just the rumours he'd been living with since Jennifer vanished.

When his lawyer, Mark Gruchy, asked why the stories changed between the first and second interview, Penney said it was because he couldn't keep a fabricated story straight. He was trying to spin a lie and not doing a very good job of it.

And then came Gruchy's final question. The question everyone had been waiting for.

"Did you have anything to do with the disappearance of your wife?"

"No, I did not," Penney said.

Under cross-examination, Crown attorney Shawn Patten was fast-paced and pointed. He challenged Penney on why he went to such lengths to include graphic and vivid details, the mallet, the plastic wrap, the blood from her ears, the exact coordinates in Hare Bay, if none of it was true.

Penney said he tried to make it look as good as possible. That gory details would make the story more believable.

Patten pointed out that Penney's version of events shifted in every single statement, to police and to the crime boss,  each time adding new details. He accused Penney of being unable to keep his stories straight because the truth kept leaking through.

Patten asked why he stayed with the organization despite the fear he claimed to feel. Penney said it was for the money,  as much as fifteen hundred dollars a week. Patten pointed out that his tax return showed he was averaging about five hundred dollars a month.

And Patten challenged the idea that Penney was too afraid to walk away. He reminded the jury that Penney wasn't fazed by gun trafficking, or shaking down a supposed biker, or yelling at a woman he believed had been beaten. He said Penney wanted the jury to believe he was a deer in headlights throughout the operation.

CHAPTER THIRTEEN — The Verdict

On May 19th, defence lawyer Jeff Brace delivered his closing argument. He spoke for nearly six hours, framing the case around what he called the three Fs: finances, friendship, and fear. He argued the RCMP exploited all three to coerce a false confession from a vulnerable man.

He told the jury there wasn't a shred of credible evidence connecting Penney to his wife's disappearance. That the Crown was asking them to rely on the testimony of professional liars dressed up in Halloween costumes. He pointed to the failed ocean searches, the inconclusive forensics, and the inconsistencies between the two confessions. He asked: if these images were real, if you had actually bludgeoned your wife with a hammer, wouldn't those details be burned into your brain?

He asked a question that did not sit well with Jennifer's family: was there even proof that Jennifer Hillier-Penney was dead?

He closed by saying: if you're sitting back and you're saying maybe, then your answer is not guilty.

The next morning, Crown attorney Shawn Patten delivered his closing. He walked the jury through Penney's shifting stories, how he only revealed information when cornered by evidence. He argued the phone call to Jennifer that evening was to make sure she was on her way home. That Penney had parked across the street, waiting.

He pointed to Jennifer's DNA on the garage wall, nearly three metres off the floor, and argued it was reasonable to conclude this was the remnants of blood splatter, the big splatter Penney himself had described.

On the two confessions, Patten offered a different theory. He argued Penney was paranoid during the first interview, he even suspected the crime boss might be a police officer. He gave fake coordinates so that if they searched, they'd find nothing. But a week later, when no arrest came, Penney felt more comfortable. The second confession was more detailed because Penney was finally giving the real truth.

As for Penney's finances, Patten pointed out that he had assets he never put up for sale, including the family home he'd inherited. He asked the jury: would you really rather confess to a murder you didn't commit than sell your house?

And on motive, Patten was blunt. He said Penney was jealous and angry after his wife left him. That he couldn't stand the thought of her being with anyone else. He reminded the jury of the text messages, Dean desperate to get her back, furious about losing half of everything. And he reminded them of Penney's own words to a police officer three days after the disappearance, when he expressed worry about being left with all the payments and expenses.

Penney said those words, Patten told the jury, because he had already moved on.

On Wednesday, May 20th, Justice Khaladkar delivered his charge to the jury, a 60 page document that took nearly five hours to read. He opened with a line that cut the tension in the room: "There's an old story -  how do you eat an elephant? One bite at a time."

He walked them through the law. The difference between first-degree murder, second-degree murder, manslaughter, and acquittal. He told them that even if they believed Penney was likely or probably guilty, that was not sufficient. The standard was beyond a reasonable doubt.

He warned them about the risks of Mr. Big confessions. He told them coercion involves the use of threats or inducements, express or implied, such that the accused's will is overcome. He told them to consider the alternate suspect theory, that if the evidence about Derick Hillier raised a reasonable doubt, they must find Penney not guilty.

The jury was sequestered that evening. Their phones were taken. The televisions were removed from their hotel rooms. They had nothing but each other and the evidence.

On Friday, they returned to the courtroom to request unedited copies of both crime boss interviews, the versions where Rudy's face was not blurred. Penney had testified the blurred video hid how aggressive and red-faced Rudy became. The jury wanted to see for themselves.

And then, on Sunday morning, May 24th, 2026, the court received word at 9:00 am. The jury had reached a verdict.

The courtroom was packed. Jennifer's family and friends filled the front rows, including Marina Goodyear, who had testified against her father and sat in the courtroom throughout the entire trial. RCMP and RNC officers lined the walls. Extra sheriffs were on hand.

The twelve-member jury,  seven women and five men, announced their decision at 10:10 a.m.

Guilty. First-degree murder.

Jennifer's family screamed. Dean Penney remained very solemn.

The 53 year-old fisherman from St. Anthony, who has been in custody since his December 2023 arrest, was taken back into custody to await sentencing. In Canada, first-degree murder carries a mandatory sentence of life imprisonment, with no eligibility to apply for parole for twenty-five years.

EPILOGUE

Jennifer Hillier-Penney has never been found.

Six diving missions. 133 anomalies investigated. Sonar, remote-operated vehicles, and the Royal Canadian Navy. They searched for a year and a half in the cold waters off Newfoundland's Northern Peninsula.

Every single anomaly turned out to be a rock, or something natural on the bottom.

Whether her remains lie somewhere in the depths of Hare Bay, scattered by a decade of tides and currents, or whether the truth about what happened that night is something only Dean Penney truly knows, that is a question that may never be answered.

What we do know is this: a woman vanished from a small town. Her belongings were left behind as though she had simply walked out of her own life. Her estranged husband told three different stories to police, then told two more to a man he thought was a mob boss. Her family waited nearly ten years for justice.

And a jury of twelve, after listening to eight weeks of testimony, after watching hours of secretly recorded confessions, after hearing from undercover officers who became the accused's closest friends, decided that they believed Dean Penney's words on that yacht.

Not the words where he said he was innocent.

The other ones.

If there's something this case teaches us, it's that the truth doesn't always leave evidence behind. Sometimes there is no body, no weapon, no forensic trail. Sometimes all you have is a story told in a room by a man who thought no one else was listening.

And sometimes that's enough.

This episode was written, researched, and produced by me, Ryan Dell. If this is your first time listening and you liked what you heard, please take a moment to give me a five-star review. It helps the podcast grow and helps other people find these amazing stories.

I love hearing from you. If you have a story I should cover, please send me an email. My email is: canadiancrimecast@gmail.com

I'm Ryan Dell, and this is Canadian CrimeCast: Coast to Coast True Crime.

*Sources: CBC News, The Telegram