Should one of Canada’s longest-serving female inmates be granted ‘mercy’?

The woman pauses for a second. She lifts the sleeve of her sweatshirt to wipe the pepper spray from her face, then folds her hands behind her back and drops to her knees, clearly resigned to the handcuffs that are quickly snapped on her wrists.

So it ended, an incident lasting 18 minutes during which an agitated Serena Tobaccojuice, currently one of Canada’s longest-serving female inmates, blocked the door of her Nova Scotia prison unit, grasping tweezers bent into a weapon, threatening and preventing two guards from leaving.

How Tobaccojuice, a Cree woman from Saskatchewan, ended up facing charges in Truro, N.S., 3,000 kilometres from her home province, is now at the heart of an extraordinary argument in the criminal case she faces involving the two correctional officers.

Her defence lawyer is asking a judge to grant the 43-year-old convicted killer, who has a record of multiple prison hostage-takings, the most lenient sentence available for an adult in Canada: an absolute discharge.

“It's an acknowledgment by this court that for the first time in this woman's life, consideration is actually being given to her history for the first time, and that for the first time, she's going to be given mercy, essentially,” her lawyer, Jeremiah Raining Bird, told the court in June.

The incident on Oct. 26, 2022, at Nova Institution for Women, captured in video surveillance footage entered as evidence in court, ended with no injuries to the guards, who stood calmly throughout. Originally charged with two counts of hostage-taking, Tobaccojuice pleaded guilty last year to the less serious crime of unlawful confinement.

This week, Nova Scotia provincial court Judge Ian Hutchison will hand down a sentence, more than three years on from the date of the offence and following a hearing that has stretched sporadically over months.

It has included evidence about Tobaccojuice’s nearly three-decade-long path through the federal corrections system, often with lengthy periods in isolation, the suffering of her childhood, and in the words of one witness, the “litany of systemic failures” she has faced.

She has, according to her lawyer, “never had a chance.” As a child, she witnessed terrible crimes. She was stabbed at the age of eight, the court has been told. She began drinking alcohol at seven, and was hospitalized for alcohol poisoning at 11.

She was placed in foster care by child protection officials. She was called racial slurs, and told not to speak her Indigenous language, according to her lawyer. Her extended family was forced to attend residential school.

Even her name has been the subject of discussion. Long called Serena Nicotine in both the justice system and the media, she has said her correct surname is Tobaccojuice, a mix-up stemming from a police officer’s mistake when she was a youth. Tobaccojuice is the name now used in court.

Her past also comprises a disturbing criminal record. She is serving a life sentence for murder in the 1997 stabbing death of 58-year-old group-home caregiver Helen Montgomery in North Battleford, Sask. Tobaccojuice was 15 at the time, as was a second teen convicted in the case.

It was a crime that drew widespread attention and prompted calls to toughen the youth justice system. In 2005, the Saskatchewan government apologized to Montgomery’s family and paid them $142,500 in compensation.

The murder conviction means that no matter what sentence she is handed in the Nova Scotia case, Tobaccojuice’s ultimate release from behind bars, if ever, will be up to the Parole Board of Canada.