Mr. Big stings are inadmissible by default. Here's why Dean Penney's was allowed at trial

Dean Penney was sentenced to life in prison without the possibility of parole for 25 years for the first-degree murder of his estranged wife, Jennifer Hillier-Penney. He was arrested following a pair of confessions to an undercover police officer posing as the leader of a criminal organization. (Ryan Cooke/CBC)Social SharingIn a murder case with no body and very little physical evidence, Dean Penney's admissions to an undercover RCMP officer posing as a crime boss were everything.

Penney confessed twice to killing his estranged wife, Jennifer Hillier-Penney, and disposing of her body in the ocean near his cabin. The videos were damning — some jurors appeared shaken as family members wept in the courtroom.

But it was never guaranteed the jury would hear the videotaped confessions.

The RCMP used a covert tactic known as a Mr. Big sting, in which police get close to a suspect and invite them into a fictitious criminal organization. The operation ends in an interview with the head of the organization, who attempts to elicit a confession.

Mr. Big stings are presumptively inadmissible in Canadian law. Before a trial begins, the Crown must establish the probative value — how the confessions help establish the truth of an allegation — outweighs the prejudicial effect of the operation.

Justice Vikas Khaladkar published his pre-trial decision on Wednesday, showing why he allowed the confessions to be played for the jury.

Justice Vikas Khaladkar presided over the case in Supreme Court in Corner Brook, including pre-trial applications on the admissibility of key pieces of evidence. (Ryan Cooke/CBC)The rules on Mr. Big stings were largely established by the Supreme Court of Canada in the 2014 case of a Newfoundland man accused of killing his daughters near Gander.

The top court found the RCMP ran afoul of Nelson Hart's rights on several fronts in that investigation, resulting in a framework for how Mr. Big operations should be handled by courts in the future.

Khaladkar said he had to consider seven aspects of how the confession was obtained.

The covert investigation into Dean Penney lasted more than four years.

"On its face, that is a lengthy period," Khaladkar wrote. "However, the evidence presented explains much of the delay."

Penney was a fisherman and told his contacts within the fictitious criminal organization that he would be unavailable during the fishing season.

The COVID-19 pandemic also played a significant role. The undercover operators testified at trial about concerns they could inadvertently bring the virus to the small community, especially given the age of Penney's parents at the time.

There was also a stretch where Penney had changed his phone number and couldn't be reached.

There were 71 documented scenarios over the course of those four years.

Over the span of the investigation, the scenarios varied greatly — from snowmobiling and watching movies at Penney's cabin, to smuggling weapons off a military base and stealing fuel near the U.S. border in Alberta.

"When one looks not simply at the passage of time, but at the actual number and nature of the interactions, I am not persuaded that either the length of the operation or the number of scenarios undermines the reliability of the confession," Khaladkar wrote.

Khaladkar had to examine Penney's relationships with all the undercover operators, but one in particular deserved closer attention.

An officer who went by the pseudonym Vic ingratiated himself with Penney far more than the others. Testimony at trial showed Vic became Penney's best friend — to the point where Vic told the court he hoped the investigation would have proved Penney was innocent.

But Khaladkar said Penney's situation was much different than the one presented in the Nelson Hart case, where the accused was "socially isolated and highly vulnerable to the relationships created by the operation."

"Mr. Penney had existing social and familial ties in the community, and those relationships remained intact during much of the operation," Khaladkar wrote. "In particular, he had the support of his mother while she was alive, and he continued to have the support of his father, with whom he shared his fishing earnings."

Penney also still had a relationship with his youngest daughter, Deana, and was living with a girlfriend at the time of the investigation. A pre-sentence report conducted before Penney's sentencing said the couple has since gotten engaged.

Penney was paid about $27,000 in total over the 71 scenarios across four years of the operation.

At the time of the confessions in 2023, Penney had fallen on hard times. The family fishing business suffered after the death of his mother, and his father's failing health meant he could no longer work.

"Even so, I do not find that he was destitute or without alternatives," Khaladkar said, noting he still had two properties and a number of vehicles he could have sold.

"In my view, the money paid over time was not particularly significant. Certainly, it was not sufficient to be coercive or overwhelming," the judge continued. "I do not doubt that he had a cash-flow problem. However, I am not persuaded that his financial circumstances were so desperate as to make a false confession reasonably likely."

Khaladkar said Penney did not experience any threats during the course of the Mr. Big operation.

He said he was satisfied there was evidence that the undercover officers "took care not to suggest that the accused would suffer physical harm if he withdrew from the organization or declined to continue."

The undercover officers told the court several times how they always offered Penney an exit ramp before a scenario. They said he could have left the organization at any time, but he chose to stay involved.

Leading up to the interrogation, Penney had been told another member of the organization, Ryan — who was said to be terminally ill — was willing to take the fall for Penney and admit to killing Hillier-Penney.

"In order for that to be effective, it was intimated to Mr. Penney that he would have to honestly disclose exactly what happened so that Ryan’s confession would match the forensics," Khaladkar said. "The crime boss needed to know everything that happened, including the particulars of the disposal of the body."

The defence argued Penney was intimidated by the fictitious crime boss during the first interview, which took place on a yacht in Vancouver harbour. Penney was being interviewed for a job as the yacht's captain.

Khaladkar did not find there were any threats.

Penney only had a Grade 8 education, but Khaladkar said he wasn't convinced his lack of schooling made him "intellectually limited or unusually vulnerable."

The court was told Penney completed courses at the Marine Institute and obtained a mariner captain's certificate.

There was also evidence he was aware of Mr. Big stings. Before his first confession, Penney expressed concern someone could "walk in through here and whack the cuffs on me."

"Mr. Penney is not unsophisticated," Khaladkar wrote.

Khaladkar found Penney's confession provided several details that were not publicly known, which strengthened the Crown's argument that the probative value of the information outweighed the prejudicial nature of the investigation.

The prejudice, Khaladkar wrote, was presenting a side of Penney to the jury that showed a man who was willing to participate in organized criminal activity such as smuggling weapons, stealing fuel tankers and moving stolen diamonds.

"But that prejudice can be managed by proper instructions and by careful control over what aspects of the operation are actually placed before the jury," Khaladkar wrote. "It can also be managed by ensuring that the jury sees only a representative number of scenarios."

For example, Khaladkar wrote: "It is not necessary to place each and every scenario before the jury, particularly the one in which Mr. Penney confessed to UC-Vic that he had, in a fit of rage, used a hammer on a ram that had butted him. That aspect of the operation would likely carry disproportionate prejudicial effect and need not be led."

With those seven boxes checked, the judge moved to the final hurdle: whether or not the operation amounted to an abuse of process. The defence never claimed it did, but Khaladkar formally ruled it did not.

"The evidence given by Mr. Penney does not displace the strong showing made by the Crown, on a balance of probabilities, that the accused’s confession to the crime boss is reliable and therefore admissible," he said. "Whether the confession is ultimately accepted, and the weight to be given to it, are matters for the jury."

The jury deliberated for parts of five days in May, before returning with a guilty verdict.

Penney was sentenced last week, receiving the mandatory life sentence without parole eligibility for 25 years.

When asked if he had anything to say, Penney proclaimed his innocence and said he hopes "to be vindicated soon."

Download our free CBC News app to sign up for push alerts for CBC Newfoundland and Labrador. Sign up for our daily headlines newsletter here. Click here to visit our landing page.

Ryan Cooke is a justice affairs reporter based in St. John's. He can be reached at ryan.cooke@cbc.ca.