BRACEBRIDGE, Ont.—pc28city Coun. Michael Thompson was portrayed in court Monday as someone who duped a young woman into joining him at a friend’s cottage with “false promises,” then plied his guests with alcohol before allegedly sexually assaulting two of them.
Thompson, 64, has pleaded not guilty to two counts of sexual assault; his lawyer, Leora Shemesh, says he vigorously denies “any and all allegations.”
On Monday, on the first day of trial at this Cottage Country courthouse, Crown attorney Mareike Newhouse gave Justice Philop Brissette an overview of the case — a rare criminal prosecution of a sitting pc28councillor who remains active in municipal politics.
On Canada Day weekend in 2022, Newhouse said, Thompson massaged one woman in a sexual manner “to which she did not consent” and, hours later, “forced himself” on another woman who was “very, very drunk.”
The second complainant “clearly remembers telling him no,” Newhouse said; despite this, she will testify Thompson put his penis on her and ejaculated on her, she said.
The two complainants, whose identities are covered by a publication ban, are expected to testify at trial later this week.
Newhouse opened her case on Monday by calling to the witness stand a university student who also cannot be identified.
She testified she was 22 when she first met Thompson at a Yorkville art gallery, and initially had no idea who he was. “He approached me asking questions and insisted we have wine,” mentioning he had “connections in the creative sphere,” she said.
It was “pretty obvious the way I was dressed that I was a creative,” the now 24-year-old said, explaining that she agreed to meet him again that night at a nearby restaurant. Once there, the six-term councillor, who represents Ward 21, Scarborough Centre, led her to believe he “has control over finances in these creative programs around the city,” she said.
The encounter “seemed like a cool alignment of events,” she said, testifying that Thompson seemed like he could be her “mentor” and that he presented himself as “someone who would look out for me.”
He later drove her to her suburban home north of Toronto; before she got out of the car, she said he handed her two $50 bills and “insisted I take it,” which she did. (During cross-examination, she rejected defence lawyer Shemesh’s suggestion that Thompson gave her the money because she’d told him about the hardships she faced as a student.)
The woman testified that Thompson mentioned a “future weekend of networking” up at a cottage, where the guest list would include a mixed group of male and female professionals.

The Muskoka cottage of pc28lawyer Calvin Barry, where Coun. Michael Thompson was accused of sexually assaulting two women over Canada Day weekend in 2022.
calvinbarrylaw/XAs the Canada Day 2022 weekend drew closer, she said she was concerned that “all of a sudden, the original people couldn’t make it,” but was glad to hear another woman with a professional background would be present.
Thompson picked her up at her home on Friday, July 1, and they drove to Port Carling, in Muskoka. They spoke about politics, and navigating the world as a Black person in “prominently white affluent spaces.” At one point, Thompson called Premier Doug Ford to wish him happy Canada Day. (The witness testified she felt he did it to impress her.)
At the cottage — which she described as “relatively big” but older — she said Thompson “encouraged a certain flow of events” by offering drinks. Still, she felt comfortable knowing that many of her friends from high school were also in nearby in Muskoka for the long weekend.
Another woman, Thompson’s friend Tracy — no last name was given — arrived within an hour, and they smoked some of her homegrown cannabis. At first, she testified thinking, “my mentors are chill,” but her ease slowly dissipated.
The other woman invited her to “test the bounciness of his bed” and then, at some point — she didn’t know if it was the first or second day — she thought she heard Tracy and Thompson “kissing or something,” which made her confused, as Thompson had presented their relationship as “friendly.”
At another point, while sitting outside the cottage, the witness said Thompson casually told her: “Feel free to get naked,” to which she said, “No, I’m good.”
Later, she said she noticed “red flags” as she chatted with the older woman, including that the other woman began pouring clear alcohol into her cup — “She was definitely trying to get me intoxicated,” the witness testified.
“I started to get very iffy” about her,” she said, explaining that she began taking only sips from shot glasses and discreetly throwing the rest over her shoulder.
“In what way was he (Thompson) influencing the level of drinking,” Newhouse asked.
He “was always making sure I’m taken care of … by (having) a drink in hand,” the witness responded.
Shemesh challenged this during her cross-examination, pointing to her police statement where the woman described Thompson as “asking” her if she wanted a drink. She also played in court snippets of cellphone video — taken from the witness’s phone — capturing her drinking wine and “cheering” with Tracy.
“You’ll agree with me that he doesn’t force you to drink alcohol?” Shemesh asked; the witness agreed, but said Thompson has a “coercive nature.”
She recalled one occasion when she was sitting by the lake in her bikini coverup, wrapped in a blanket, when Thompson approached his friend Tracy — who was topless — and “started massaging her shoulders and whispering to her.” She said Thompson suggested for a second time: “Feel free to get naked.”
“I was really uncomfortable,” she said, testifying she eventually went to bed.
The next day, the witness said she expected more people “to be flowing in.” Instead, two women — the complainants — arrived with a dog.
The witness said she saw Thompson getting “feely” with the new arrivals, and saw him massaging one of the complainants.
By this time, she said, Tracy had left, and the witness said she bonded with the two new women as they processed “what was going on.”
The next morning, the woman testified she spoke to the complainants. In court, the prosecutor told her not to repeat what they said, but asked her to describe their demeanour.
Both expressed shock, anger, confusion and feeling “taken advantage of,” she testified.
At the end of the weekend, the three women left together. The witness had originally planned to return with Thompson, and when she told him she was leaving without him, he was visibly annoyed, she said.
Did you hear from him again, Newhouse asked?
“No, I was ghosted,” the woman said, adding he never followed up on his “false promises.”
Shemesh will resume her cross-examination when the trial resumes on Thursday.