Two men who sexually assaulted and drugged a 24-year-old woman for several hours at a downtown Toronto bar have been sentenced to nine years in prison, but one may soon be released on bail pending an appeal that is almost certain to succeed.

“This was a prolonged, violent and degrading sexual assault,” Superior Court Justice Michael Dambrot said, delivering his sentencing decision in a downtown courtroom Wednesday morning. College Street Bar owner Gavin MacMillan and bar manager Enzo DeJesus Carrasco were “callous to a degree that is difficult to comprehend” throughout the assault, the judge said.

“The victim was visibly and significantly impaired, stumbling and crashing into tables, and ultimately was either asleep or unconscious seated at a table,” he said. “When the sexual activity commenced, her condition was little changed.”

Dambrot found that the victim was unconscious or virtually unconscious while being simultaneously sexually assaulted by both men, and that she never consented to any of it. The two men also gave her cocaine to keep her awake and available for their sexual gratification, he said.

“She was not consenting and the accused could not have imagined that she was,” he said.

The “two predators” might have engaging and charming public personas, Dambrot said, but “they have a deep sense of entitlement and profound disrespect for the personal integrity of women.”

The sexual assault might have begun as a “crime of opportunity” but, as it went on, it became a “well-orchestrated and chillingly deliberate horrendous crime that calls for exemplary sentences,” he said.

DeJesus Carrasco, 34, who faces two more trials on three counts of sexual assault involving three complainants, has been in custody since the jury verdict in November. MacMillan, 45, had been on bail pending his sentence but was taken into custody after the sentence was passed

Both men are appealing their convictions on the basis that they were forced to choose a jury under a new procedure introduced by the Liberal government that came into effect in September, after they had already chosen to be tried by a jury.

In a ruling overturning a murder conviction, the Court of Appeal last month found that the old jury selection procedure should have been used in cases that predated the change in law. As a result, the College Street convictions are going to be overturned despite a “very, very strong Crown case,” Court of Appeal Justice James MacPherson said Wednesday afternoon at MacMillan’s hearing for bail pending appeal.

“There is going to be another trial,” the judge said. “This is very unusual.”

The Crown opposed bail for MacMillan given the seriousness of the offence and lengthy sentence, and said that Crown is will seek to appeal the jury selection decision at the Supreme Court of Canada.

MacMillan’s appeal lawyer Breana Vandebeek said it is agreed that MacMillan has never violated his bail over three years, is not a flight risk and that any risk to public safety can be managed in the community with strict bail conditions.

A decision on whether MacMillan will be released on bail pending appeal is expected next week.

DeJesus Carrasco has also filed a notice of appeal but has not sought bail. He faces three more sexual assault charges at two judge-alone trials set for July and March.

A jury found the two men guilty of gang sexual assault and drugging to facilitate a sexual assault after deliberating for four days last November.

The jury could not agree on whether the two men unlawfully confined the woman on the night of Dec. 14, 2016, and whether DeJesus Carrasco raped her the following morning at his apartment. The Crown dropped those charges after the jury verdict. DeJesus Carrasco was acquitted of a sexual assault charge from when he was alone at the bar with the victim earlier in the night.

Juries do not give reasons for their decisions.

In order to find both men guilty of sexual assault, the jury had to find they committed a sexual assault during at least one point during the hours of sexual acts at the bar, which was closed to the public that night after a bartending class. The victim, who was visiting Toronto, had come to the bar to see a friend who was taking the class.

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During the trial and at sentencing, the Crown and defence presented two very different versions of the events that night, which were captured on security cameras at the bar that did not record sound.

The Crown sought a sentence of 12 years in prison for both men, stressing the “catastrophic” impact on the victim, who has lasting physical and psychological injuries.

Dambrot, who is now presiding over the first-degree murder trial of Kalen Schlatter, said he has not yet been able to write full reasons for his decision but gave a brief summary of what he found to have happened on the night of Dec. 14, 2016.

He entirely rejected the defence position at trial, which was that the victim was consensually dominated by the two men at her own explicit request. “No reasonable person who views the video of these events could think” that the victim was pretending to be unconscious and was directing the sexual activity, and that the two men were obeying her commands, he said.

He also said it was “entirely incredible to imagine that a woman being violently sexually assaulted by two men while she was unconscious or virtually unconscious would awake from her unconsciousness, find herself being abused in this horrific way and would not only immediately consent to it continuing, in fact continuing for many hours, but more than that, would take over as the director of the activity, requiring it to continue even when the offenders were prepared to end it.”

Dambrot said that, viewed in isolation, there are moments in the video where it appears that the victim was consensually engaging in some of the subsequent sexual activity. “But that would be to ignore reality” as well as that the two men were also found guilty of drugging the victim in order to sexually assault her, he said.

MacMillan’s defence lawyer, Sean Robichaud, had argued that the judge should find that the sexual assault was limited to only one portion of the night, in the main area of the bar. He said in that case, a sentence of 12 months would be appropriate.

DeJesus Carrasco’s lawyer, Uma Kancharla, said the sexual assault should only apply to one instance near the start of the sexual activity, where the victim appears to lose consciousness. She argued a six-month sentence should be given.

Both defence lawyers said a sentence of two years would be fair, based on the Crown’s version of events.

The victim, whose identity is under a publication ban, was not in court but her mother was.

“All we wanted is, for once, victims to be able to come forward and speak up, and not to be put through the hell that they have been,” said her mother. “Both her dad and I are so proud of her that she did this.”

With files from the Canadian Press