Dean Penney pledges ‘150% honesty’ to fake crime boss in interview played in court

Over the course of about 90 minutes of a recorded conversation between Dean Penney and a fictitious crime boss, a theme emerged: Honesty.

“I don’t give two shits if you lie on your taxes,” the crime boss, an undercover RCMP officer with the pseudonym of Rudy, told Dean Penney. “The person you don’t f–king lie to, who do you think that is?”

“You,” Penney replied.

“Hundred per cent,” Rudy answered.

Rudy served as the head of a fictitious crime organization, part of a years-long Mr. Big operation set up around Penney to bring him in, make him comfortable, and ultimately try to extract a confession.

The St. Anthony, N.L., man is charged with first-degree murder in the death of his estranged wife, Jennifer Hillier-Penney. She disappeared in 2016 and her body has never been found. Penney has pleaded not guilty.

Crown attorney Kate Ashton pointed to video interviews with the fake crime boss in her opening remarks of the trial, calling Hillier-Penney’s death planned and deliberate, while Penney’s lawyers said they will set out to prove a confession he gave is unreliable.

The video played at Supreme Court in Corner Brook — a four-plus hour long conversation — was started Thursday afternoon. It’s one of two interviews Penney and Rudy had.

It was recorded on Nov. 30, 2023, aboard a yacht at a marina in Vancouver. It served as a sort of job interview for Penney, who was seeking to become captain of the crime boss’s vessel.

While speaking with Penney, Rudy called the captain’s job a position of immense loyalty. Another man — also an undercover officer — was supposed to fill the role, but a fake illness took him out of the picture — and gave Penney a chance to step up.

“I’ll give you 110 per cent. What you needs done, I’ll do whatever I can.” Penney said.

Penney also told Rudy the job would be a game changer for him, outlining compounding financial stresses like a lack of work in the fishery, a mortgage and more.

But before the interview process could begin, Rudy lectured Penney on the importance of honesty. He said he had to talk to Penney about mistakes and how they’re handled.

“I want you to understand a little bit about me — how I think,” Rudy said. “What I care about is how people deal with mistakes.”

Rudy said the members of the organization were like family, and that he had a rare opportunity to choose his family.

“I get to pick and choose,” Rudy said. “If I get to pick and choose, then I better get it right.”

Shortly after, Penney told Rudy he would give him “150 per cent honesty.”

Throughout the rest of the conversation shown Thursday, Rudy asked Penney multiple times if he was nervous or scared. Penney said no, but said he was desperate for the job to work out.

Before the video was played, Rudy told the court that he had worked as a full-time undercover officer for around eight years, and has been a police officer for nearly 25 years.

He told the court that he had played the role of a crime boss in undercover operations over a dozen times, and that the purpose of the voluntary interview is to try to get as much information as possible — information that can either connect a person to an investigation or exculpate them.

When asked if the person being interviewed was in the courtroom, Rudy responded he was “seated immediately to the front of me.”

Hillier-Penney’s name did not come up over the 90 minutes shown in court on Thursday. Viewing will continue during a half-day of proceedings on Friday.

The beginning of Thursday’s afternoon session also came with instructions to the jury from Justice Vikas Khaladkar. He told the jury that Penney would be admitting to staged crimes he thought were real, and that the jury should only focus on the charge of murder.

‘Not really’ leads to heated exchange

The day started with defence lawyer Mark Gruchy finishing the cross-examination of Vic, the undercover RCMP officer tasked with becoming Dean Penney’s best friend. 

Vic is also a pseudonym, and his identity was covered from the gallery by a black curtain. He was entering his third day in the witness box, testifying on Tuesday and cross-examined on Wednesday and into Thursday.

The examination ended with a testy exchange between Vic and Gruchy, centred around two words Vic told Penney during a conversation in November 2023.

The court heard the audio recording detailing an inquisitive Penney asking about what might happen to people who cross the organization. 

“Don’t look back, man. That’s all there is to it,” Vic said in the recording. “If you ever did something stupid, then maybe that’s something different.”

Penney later asked, “Yous ever had anyone that …[we] got to get rid of them?” 

Vic previously told the court that it was made very clear to Penney that no harm could come to him, but that he didn’t expect the question in the moment.

Vic responded after a short pause, and said “No, not really. no.”

Gruchy grilled Vic on his answer, saying that “not really” inferred that violence could occur should Penney step out of line.

“You’re opening the door … that something can happen to somebody that crosses the organization stupidly. Is that fair?” Gruchy asked.

“No,” Vic responded. “I said ‘no’, and then I cleaned it up … We’re getting hung up on ‘not really.’”

Vic seemed audibly frustrated following his answer, adding that the organization was painted as a group that uses “leverage over violence.”

Gruchy then asked Vic about Rudy.

“Rudy is like the Capone of your organization, right?,” Gruchy asked, referring to the notorious mafia boss.

Vic was quick to respond.

“Except for, uh, we don’t whack people. We don’t whack each other,” he said.

When asked by Gruchy if “whack” meant killing someone, Vic replied “We don’t do that, and we never displayed that and we never portrayed that.”

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