The Feb. 11 Court of Appeal of Yukon decision in R. v. Sheepway, 2025 YKCA 1 involved Darryl Sheepway, who was convicted of shooting and killing Christopher Brisson and disposing of the body in a remote area just outside the territory’s capital of Whitehorse.
The issue before the Appeal Court was whether the sentencing judge erred in finding that he was unable to take into account the harsh conditions Sheepway endured in pre-trial custody when determining the length of time he would be ineligible for parole.
According to the Appeal Court’s written decision, a shotgun-toting Sheepway had arranged to meet Brisson in a remote area to buy crack cocaine — a drug to which Sheepway had become addicted.
But Sheepway’s real plan was to rob Brisson. A struggle ensued, and as Brisson tried to speed away in his truck, Sheepway shot twice into the rear of Brisson’s vehicle.
One on those shots ripped into Brisson’s back, killing him.
Sheepway took the crack and the cash and fled for home — only to return later to gather up the shotgun shells and throw Brisson’s body down a steep embankment.
Following a judge-alone trail, Sheepway was convicted of second-degree murder — second degree because it was found the Crown had failed to prove the murder was planned and deliberate. This finding was in part due Sheepway's “entrenched cocaine addiction at the time of the murder.”
The conviction came with an automatic 25-year life sentence, with a stipulation that “a person convicted of this charge must remain in prison for a minimum of 10 years before [being] eligible for parole.”
However, the Appeal Court notes that a sentencing judge can increase this period of parole ineligibility — right up to the maximum 25 years.
The sentencing judge in this case ruled that Sheepway would remain ineligible for parole for 13 years, even though Sheepway’s defence argued it should be limited to 10 because “mitigating factors substantially outweighed the aggravating factors.”
As part of the evidence Sheepway and his defence lawyer outlined the difficult conditions Sheepway endured during his pre-sentence custody at the Whitehorse Correctional Centre – namely, his time spent in a segregated unit; his extended time kept in a “secure living unit” cell; a lack of “programming”; a lack of social interaction; and having to deal with the “disturbing behaviour” of a mentally ill inmate.
Sheepway had said this had caused him “panic attacks and feelings of intolerable agitation.”
The trial court heard that Sheepway endured about 18 months of this before his lawyer stepped in with legal action, at which point Sheepway was allowed “unlocked contact with other inmates.”
The sentencing judge considered several decisions out of Ontario that treated harsh pretrial custody as a mitigating factor. On the other hand, he interpreted various appellate decisions as finding harsh pretrial custody to be not a relevant factor in determining parole ineligibility periods.
“Thus, the judge concluded he should give no consideration to the conditions of pre-sentence custody endured by Mr. Sheepway,” notes the Appeal Court.
In the end, the majority of the Appeal Court found the sentencing judge to have got this wrong.
“The judge heard evidence that Mr. Sheepway was held for approximately 18 months of time in conditions that were equivalent to segregated custody or in isolation from other inmates, when he was allowed very little time out of his cell,” writes Justice Susan Griffin. “This was not due to any custodial misconduct by Mr. Sheepway, and after legal action was launched by his counsel, he testified that he was allowed unlocked contact with other inmates. As noted by the judge, the medical evidence supported the conclusion that these harsh conditions had a significant negative impact on his mental health.”
Justice Griffin went on to find that it was clear the sentencing judge “accepted … Sheepway’s evidence in this regard.”
“Otherwise, there would be no need for the judge’s lengthy analysis as to whether he could take these conditions into account,” she writes.
Justice Griffin found Sheepway’s pretrial custody conditions to have been “exceptionally harsh,” that they “affected his circumstances at the time of sentencing.”
These details, she found, “should be taken into account in mitigating the term of parole ineligibility” (if that term is to be greater than the mandatory 10 year minimum.)
The Crown prosecutor at appeal, Kathryn Laurie, told Law360 Canada the ruling clarifies what sentencing judges can do in this area.
“When determining whether it is appropriate to increase the period of parole ineligibility from the 10-year minimum for an offender convicted of second-degree murder, harsh conditions of pre-trial custody that negatively impacted the offender may be considered in mitigating the term imposed,” said Laurie.
Sheepway’s lawyer, Vincent Larochelle, said the “significance of the decision extends beyond the facts of this case.”
“The Court of Appeal's decision stands for the general proposition that a variety of different circumstances can be taken into consideration when determining the period of parole ineligibility for [second]-degree murder. It also has a particular significant for Mr. Sheepway, as it provides him with some vindication for the harsh treatment he received while at the Whitehorse Correctional Centre.”
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