There was prolonged debate about what constitutes an admission of innocence as the undercover officer who ultimately got a confession from Dean Penney was cross-examined in a Corner Brook courtroom Wednesday.
The officer, who can only be referred to by a pseudonym, Rudy, played a fictitious crime boss in two interviews with Penney. Penney had been working with the group and was interviewing to become the captain of Rudy’s yacht — a staged interview as part of what’s known as a Mr. Big operation.
Penney is charged with first-degree murder in his estranged wife Jennifer Hillier-Penney’s death, and has pleaded not guilty. Hillier-Penney has been missing since Nov. 30, 2016, and her body has never been found.
Defence lawyer Mark Gruchy grilled Rudy over the beginning of the first interview, in which Penney initially told Rudy he had nothing to do with the disappearance of Hillier-Penney — and that any evidence against him was hearsay.
“I had nothing to do with it,” Penney told Rudy on Nov. 30, 2023. “I had absolutely nothing to do with it.”
But during his cross-examination on Wednesday, Rudy told Gruchy several times that despite Penney’s assertions, he didn’t see it as an admission of innocence.
“You don’t think someone saying ‘I had nothing to do with it. I did not hurt my wife,’ is not a person saying they did not commit the crime?” Gruchy asked, his voice slightly raised.
Instead, Rudy told Gruchy that he had hoped Penney would use the space to immediately provide an explanation as to why he wasn’t responsible.
“[I’m looking for him] to expand on that point as to why he’s not responsible for the offence. That did not come, and it did not come at all through the next successive parts of this interview. So there was no detail that Mr. Penney provided me explaining why he was not involved — which would be his innocence.” Rudy said in response.
“Simply stating that he was not involved or stating that he did not hurt Ms. Jennifer Hillier-Penney is not innocence. It is a statement, but it is not innocence.”
Rudy, an undercover officer who told the court he’s worked in the role of a fictitious crime boss over a dozen times, said the purpose of a crime boss interview is to discuss a person’s involvement or lack of involvement in an incident being investigated.
It can go both ways, Rudy said, either connecting someone to an investigation or absolving them.
Fictitious crime boss faces cross-examination in Dean Penney’s murder trial
Sometimes, Rudy said, tools can be used within interviews to do what he described as “overcome an obstacle.”
In this case, the tool was a fake memo created by Rudy that showed police were on Penney’s tail.
The phony RCMP memo detailed how police were weeks away from arresting Penney, and that police should be prepared for the national media attention his arrest would garner.
As part of the Mr. Big operation, Penney was made aware that the criminal organization had contacts inside the RCMP’s St. John’s operations, and that information on laptops and hard drives could be decrypted.
A memo isn’t always used, Rudy said, but it was decided to be warranted in this case. Rudy told the court the obstacle that had to be overcome was Penney not spelling out why he was innocent, and that the memo was designed to show him how serious the matter was.
“I provided Mr. Penney a memo so that Mr. Penney could understand that there was other things that may or may not exist. And so that Mr. Penney understood about the seriousness of what he and I were discussing,” he said.
Gruchy made sure multiple times to remind Rudy that the contents of the document were a lie.
Rudy said that while the part about media attention was likely true, he did say details about being close to an arrest at the time were fabricated.
Rudy added that his role, and being part of an investigation of this nature, requires “trickery and deceit.”
Rudy was covered from the view of the gallery by a large, black curtain, but was visible to the justice, counsel and the jury.
Throughout his examination, Rudy affirmed that the interview is a voluntary exercise. If Penney felt scared or fearful, Rudy said he could leave at any time.
Gruchy questioned Rudy multiple times on if his role as a crime boss would instill fear in the average person — telling Rudy that he was “playing a gangster.”
Rudy said he didn’t feel that way, and that the crime boss role is designed to instill respect as opposed to fear.
If there was a time where Penney said he felt uneasy, Rudy said he worked to figure out why and clear it up.
Penney mentioned at least two times in the first interview that he felt intimidated by Rudy as the leader of the organization.
“I alerted to it, and I spent time examining that with him to clear up whether Mr. Penney was, [or] had any fear of me or was intimidated by me. And Mr. Penney assured me that he was not scared by me. That he was not intimidated by me. It was the fact that … it was my position,” Rudy said.
“There was respect to that, but there was no intimidation.”
Questions around the second interview largely focused on additional information Penney shared during that conversation with the fake crime boss.
The undercover officer said they noticed the differences and made note of them.
“The more that we talked about it, the more Mr. Penney was recollecting and refining his timeline of the sequence of events,” Rudy said.
Rudy said reissuing the same questions was meant to get as much information out as possible. That line of questioning did lead to Penney providing new details.
For example, Penney said in the first interview that he pushed Hillier-Penney down a set of stairs, but said in the second interview that he hit Hillier-Penney with a hammer after she fell to the bottom.
Penney also changed other details from the first to second interview. Penney originally told Rudy he had placed Hillier-Penney’s body in a canvas Seadoo cover while he was aboard his boat to hide her body, but clarified in the second interview that he rolled Hillier-Penney into the canvas while in their garage.
Gruchy said he was trying to straighten the timeline, poking holes in Penney’s role as a reliable narrator.
The afternoon session ended with Gruchy telling Justice Vikas Khaladkar that he was nearly complete with his cross-examination of Rudy, but that he wanted time to speak to fellow defence lawyer Jeff Brace to ensure all of their bases had been covered.
It’s expected that Rudy will return to the witness box in Supreme Court Thursday morning before the next witnesses enter.
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