TORONTO -- Two men convicted of drugging and sexually assaulting a 24-year-old woman inside a downtown Toronto bar in 2016 have been sentenced to nine years in prison.

On Wednesday, Superior Court Justice Michael Dambrot referred to 44-year-old Gavin MacMillan and 34-year-old Enzo DeJesus Carrasco as "predators" with a "deep sense of entitlement" as he sentenced them to seven years for gang sexual assault and two years for administering a stupefying substance. The sentences will be served consecutively.

“The offenders were callous to a degree that is difficult to comprehend,” Dambrot said. “They have engaged in a charming public persona, but they have a deep sense of entitlement and a profound disrespect for the personal integrity of women.”

“These events may have begun as a crime of opportunity but as time went on it became a well-orchestrated deliberate and horrendous crime.”

Back in November 2019, 11 jurors reached a verdict following four days of deliberation. They found the two men guilty of gang sexual assault and administering a stupefying substance in connection with an hours-long incident that took place inside the now-closed College Street Bar.

MacMillan was an owner of the former Little Italy bar and DeJesus Carrasco was a manager.

In December 2016, the female victim, who is a fashion photographer, was visiting Toronto for a work event when she went to the College Street Bar to meet a friend who was an employee there. The victim’s identity is protected under a publication ban.

The trial for the two men consisted of weeks of testimony and the viewing of several hours of graphic security footage from inside the bar.

The Crown said the men sexually assaulted the victim in various rooms of the bar over a period of at least six hours. During this time, the Crown said, the suspects repeatedly dosed her with cocaine for the purpose of continuing to sexually assault her.

Both men pleaded not guilty to all charges laid against them and maintained that the sexual encounter was consensual.

“I find this a fact beyond a reasonable doubt that the victim’s cognitive ability was never fully restored, that she never consented to any of this sexual activity at the College Street Bar that was the subject matter on the count that they were convicted,” Dambrot said.

“That was exactly what the two predators who kept her that way intended. They had no mistaken beliefs she was not consenting.”

Dambrot went on to say that the victim was “visibly and significantly impaired, stumbling, crashing into tables and ultimately was either asleep or unconscious.”

‘Horrible nightmares over and over again’

At the start of their sentencing hearing on Jan. 29, the victim’s mother stood before the court and read a victim impact statement through tears, noting that her daughter did not have it in her to do the same.

She said her daughter lives with “permanent damage” and has subsequently “not been the same person for a long time.”

“Did you stop to think what if this was your daughter, your mother, your sister, your niece, your grandmother or even your friend,” she asked the two men seated in the courtroom in front of her.

“My daughter was such a happy, trusting, creative individual and it was all taken away from her.”

She said there is not a day that goes by where her daughter does not think about what happened to her that night.

The victim's mother was present inside the courtroom on Wednesday as the judge sentenced the two men. She listened intently as Dambrot read through his decision, referring to the incident as a "prolonged, violent and degrading sexual assault."

MacMillan seeks to have conviction overturned

The Crown, who referred to the assault as “invasive” and “degrading,” was seeking a 12-year sentence for each of the men – nine years for gang sexual assault and three years consecutive for administering a stupefying substance.

The defence was asking for 12 to 24 months.

The maximum sentence for convictions of gang sexual assault is 14 years and the maximum for administering a stupefying substance is life in prison.

MacMillan’s lawyer spoke briefly to reporters outside the courthouse on Wednesday about the sentence.

“Whenever a sentence like that is imposed, I think it goes without saying that a person is not going to be happy about that but I don’t have anything direct from my client one way or the other,” Sean Robichaud said.

Meanwhile, MacMillan is seeking to have his conviction overturned in light of a new ruling on jury selection by Ontario’s top court.

READ MORE: Appeal court rules some changes to jury selection process were misapplied

He filed an appeal on Jan. 23, which cites the Court of Appeal for Ontario ruling released the same day.

At the beginning of the sentencing hearing, the defence requested a mistrial on the basis of improper jury selection, but the judge dismissed the request, stating that the situation could be dealt with by the Ontario Court of Appeal.

DeJesus Carrasco also filed a notice of appeal following the sentencing hearing on the grounds that he was denied the use of the old jury selection method.