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Karolina Huebner-Makurat, known to her friends and family as Caroline, was supposed to be meeting her friend at a restaurant for lunch on July 7, 2023. Her friend became worried when she didn’t show up, and increasingly so after seeing a report on TV that a woman had been shot on Queen Street East; she repeatedly called Huebner-Makurat’s phone until a nurse at St. Michael’s Hospital finally answered. Huebner-Makurat, a 44-year-old mother of two little girls, had been killed. On Wednesday, the Crown laid out for the jury its case for second-degree murder against the drug dealer who has already admitted to firing the gun that killed Huebner-Makurat: Damian Hudson. Tensions had been simmering for days between Hudson and other dealers, which reached a boiling point on July 7, 2023, when two men robbed Hudson of a satchel, leading to a gunfight in the middle of the day on Queen Street East near Carlaw Avenue. Huebner-Makurat was caught in the crossfire as she crossed the street on her way to meet her friend. The killing attracted intense public scrutiny, given that the violence had spilled out from the courtyard of the South Riverdale Community Health Centre, which at the time housed a safe-injection site for drug users on its ground floor. The events leading up to the shooting Crown attorney Michael Wilson, prosecuting the case with co-counsel Paul Zambonini, told the jury that workers at the site are expected to testify in the coming days that there was “in effect an open-air drug market in the courtyard directly west of the health centre,” taking advantage of the opportunity to sell illegal substances to the “steady stream of users” at the stie. Hudson was a known drug dealer who sold his product in that courtyard. A few months before the killing, he had begun texting a worker at the site, Khalila Mohammed, asking her to connect him with users to help sell his drugs; she refused. Around the same time, Mohammed, who is also expected to testify at Hudson’s trial, became close with another drug dealer who became a regular fixture at the site, Ahmed Ibrahim. “Khalila Mohammed regularly encountered him; she spent time talking to him both on her rounds and during her breaks,” Wilson told the jury. Three days before the killing, Mohammed and Ibrahim were spending time in the courtyard, when Mohammed noticed Hudson “pacing back and forth at a distance, glaring; she took note of the behaviour, she thought it was weird,” Wilson said. Later that night, Hudson texted her: “f---in’ goof you wanna work with the opps if that’s wiz from Teesdale I’m smoking him.” Mohammed is expected to tell the jury that “opps” means “opposition,” and that “I’m smoking him” means “I’m shooting him.” As for “wiz from Teesdale,” Wilson told the jury they will hear evidence that “wiz” is another drug dealer, Ahmed Ali, who in July 2023 was an associate of Ibrahim’s and that they resided in neighbouring apartment buildings in Scarborough on a street called Teesdale Place. Mohammed didn’t see the message until the following morning, telling Hudson that if he had something to say to her, he should say it to her face. Hudson later responded: “Hang with my opps you gonna die with emm.” Mohammed shared the text with Ibrahim, who told her he would “take care of it,” Wilson told the jury. This led to a heated text exchange between Ibrahim and Hudson. Ibrahim denied being from Teesdale, and Hudson later responded: “I don’t care about jail or cameras buddy robbed me” — referring to “wiz” — and “I don’t need to plan I’ll up it on site anywhere.” Wilson told the jury: “It will be for you, ladies and gentlemen, to determine how you interpret the phrase ‘I’ll up it on site,’ but based on the evidence called at this trial, it will be open to you to find that the phrase means ‘to pull a gun on sight anywhere.’” Wilson explained that Hudson appeared in the text messages to accept that Ibrahim was not from Teesdale, didn’t know who “wiz” was, and hadn’t been involved in robbing him. “Toward the end of the conversation, the two men appeared to be friendly with one another,” Wilson said. However, later that night, Hudson texted Mohammed, accusing her of working with Ibrahim and suggesting she might be setting him up to be robbed. He told her, “I’m the new captain,” which she interpreted to mean “I’m the new big drug dealer” at the safe-injection site courtyard. “This is the context in which the events of July 7, 2023, took place,” Wilson said. “Damian Hudson was a drug dealer at the site, he had been robbed, he had threatened to ‘smoke’ the person who robbed him, and he had said he didn’t care about jail or cameras. He was willing to ‘up it on site anywhere.’” The shooting of Karolina Huebner-Makurat Surveillance footage shows Ibrahim, Ali and Hudson arriving at different times at the safe-injection site on the morning of July 7, 2023. Within two minutes of Hudson’s arrival, Ibrahim and Ali text each other, but police do not have the content of those messages, Wilson said. In the 40 minutes that followed Hudson’s arrival, he and Ibrahim appeared to spend time in the courtyard with no issue, but “the peace between these two men was temporary,” Wilson said. An armed Ali, who had left the site before Hudson’s arrival, returned to the area by bus around 12:20 p.m. What happens next, Wilson said, is Ali and Ibrahim “set upon Damian Hudson.” Based on surveillance footage and expected witness testimony, Wilson said the two were trying to rob Hudson, intent on taking a satchel Hudson was wearing across his chest. Ali struck Hudson with his gun, Wilson said, as footage played during the Crown’s opening statement shows two men chasing after a third down the busy street, jumping on him and bringing him to the ground, grabbing the satchel and running away. Hudson chased after his assailants. He caught up with them near the safe-injection site courtyard, where the men struggled, and Ali again struck Hudson with his gun. A worker at the site standing near the altercation is expected to testify that he saw Hudson on the ground pull a gun out of his pocket and point it toward Ali, who had his gun pointed toward Hudson, and they started shooting at each other. Huebner-Makurat was crossing the street when a bullet penetrated the right side of her abdomen, and she died from a severe loss of blood. Another worker at the site, Derek Venman, took cellphone video of the altercation. He testified briefly on Wednesday as the Crown’s first witness. “Next thing you know, shots were fired, and that poor woman got hit,” he testified. The trial continues on Thursday.
