From the box for the accused, Douglas Hales stared at the men who befriended him six years ago.

Clean-cut and wearing suits, each undercover RCMP officer stood throughout long hours of testimony at Hales' first degree murder trial.

Hales is one of the last people ever seen with Daleen Kay Bosse. The Saskatoon mother and student teacher was 25 years old when she disappeared a decade ago from a Saskatoon nightclub where Hales worked as a doorman.

  • CBC's Jennifer Quesnel is tweeting live from the courtroom. Head to the bottom of this page to follow the case

Starting May 6, 2008, undercover RCMP officers posing as car repossession men approached Hales and his common-law wife at their duplex in White Fox, Sask.

Over the next three months, the undercover officers paid Hales more than $6,300 to run a series of errands across the country, aimed at making him feel like a member of a criminal organization.

daleen bosse

Daleen Bosse (CBC)

Within a week, Hales told the first supposed car repo man he was his only friend.

"You knew he was unemployed, you knew that he needed money," noted Hales' defence lawyer Bob Hyrcan, during cross-examination of one of the undercover officers in "Operation Frendo."

"Yes, like anybody else," replied the RCMP member.

"Yes, but not everybody is the young father of a child with special medical needs," said Hrycan, who noted none of the undercover officers have any formal degrees in psychology. "He needed money to support a family and a sick child, that never crossed your mind?"

The elaborate RCMP set-ups included a staged assault on the ex-girlfriend of a gang member, played by a female RCMP member. On a subsequent trip to Casino Regina, Hales believed he overheard the casino's head of security telling his "criminal" associates he could change time stamps on the casino's surveillance footage, to provide them with an alibi. 

"It was all smoke and mirrors," said the undercover sergeant who masterminded each scenario.

By the end of the three months, Hales was ready to take on a 'big job' for the undercover officers that would net him $22,000. His 'associates' warned him to be completely truthful with the big boss, who wanted to check him out.

"It was very much in his interest to portray himself as a hardened criminal and you knew that?" Hrycan asked another undercover officer. 

"No," replied the officer. "He was advised to tell the truth."


CBC's Jennifer Quesnel is covering the story. Follow her tweets live from the courtroom.