The trial has begun for a Vaughan man charged with the second-degree murder of his girlfriend’s close friend, shot to death two years ago.
It was May 11, 2024, just after 5 a.m. when police were called to a 695 Northcliffe Blvd. near Eglinton and Dufferin streets. Inside unit 404, first responders found 20-year-old Makayla Roxburgh-Carpino suffering from life-threatening injuries. She would die at the scene.
Later that evening, 27-year-old Harold Santana Simon was arrested and charged with murder. He has pleaded not guilty.
Assistant Crown attorney Geocelyne Meyers told the jury in her opening address that Simon fired a bullet into Roxburgh-Carpino’s head after he let himself into Sentoree Kamara’s apartment. The two women were sleeping in Kamara’s bed only minutes before.
“You will hear from several witnesses whose evidence will help you decide what happened in that room and what Mr. Simon’s intent was when he pulled the trigger,” said Meyers.
Kamara, the first witness to take the stand, testified Wednesday that she dated Simon for about three years, but he was her “former” boyfriend at the time.
Kamara described their relationship as toxic, calling him jealous and controlling. She said she had told others, including Roxburgh-Carpino, who she described as a very close friend whom she saw daily, about her concerns regarding Simon.
Kamara said she had given Simon a key to her apartment because periodically she would ask him to check on her 10-year-old son, or to pick him up as he was coming off the school bus. Kamara said she asked for Simon to return the key at least five times in the days before the shooting.
She told court the couple were not talking and said she had blocked him on Instagram and on text.
“He was upset. He was calling, texting, telling me to unblock him,” Kamara said.
Kamara said she last saw Simon about a week before the shooting when he randomly popped by the apartment and let himself through the front door. Video surveillance was shown from May 7 at 3:30 a.m., showing a man Kamara identified as Simon walking through the lobby of the apartment building.
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On the evening of May 10, Kamara said she and Roxburgh-Carpino decided to go out for drinks near Black Creek and Trethewey drives. While at the bar, she said Simon direct messaged either her or her friend through Instagram writing, “This is Santana. I have the phone.”
Kamara said she believed the message to mean that Simon had her son’s phone, explaining her son was home alone at the time.
“I have two phones. My iCloud is connected to both,” she explained.
“He was going through the phone. He was going to see me talking to men, I just figured.”
A direct message exchange between an account associated with Simon and Roxburgh-Carpino over Instagram was also shown, in which the user associated with Simon wrote “she deliberately trying to ruin my life, smh.”
In addition to the back-and-forth messaging on Instagram, Kamara said that Simon called Roxburgh-Carpino. She testified that she had videotaped the conversation between the two on her phone because Roxburgh-Carpino had it on speaker.
The video captured the voice of Roxburgh-Carpino saying, “You stole her house key. You’re stalking her. You’re a stalker.”
Kamara said she couldn’t remember how the phone call ended but said when she returned home, she learned from her son that Simon had been in her apartment, removed her TV from the wall mount and taken it with him.
“There was no TV on the wall,” Kamara said, explaining that she was anxious that Simon was “going to appear. I knew he wanted to talk about what he seen (sic) in my phone.”
She said the two went to bed about an hour later. Roxburgh-Carpino was sleeping on the side of the bed near the window, she was lying on the right side of the bed near the door, which was closed.
As they were sleeping, Kamara said she heard the front door to the apartment open before Simon barged into her room and woke she and Roxburgh-Carpino up.
“He was telling Makayla to come out of the room. He wanted to talk to me,” said Kamara, who said he was angry and loudly yelling.
“I was telling him to keep his voice down because my son was sleeping. He just looked very angry. He was pacing. He couldn’t contain himself. He was going up in her face. He just kept saying ‘get out of the room’ and he was calling us ‘whores.'”
Kamara said Simon then went into the living room and came back with a firearm in his hand.
“He just kept saying ‘get out of the room,'” she said.
When the Crown asked what Roxburgh-Carpino was saying. Kamara answered: “She was confused. She was asking him, ‘What is this for? What is this all about?'”
“I seen (sic) him put the gun to her head and shoot her,” Kamara told court, breaking down in tears, explaining Roxburgh-Carpino was sitting on the side of the bed and Simon was standing right in front of her.
“I got up and asked him what he did. He ran out of the house. I ran to Makayla, tried to put pressure on her wound and called 911,” Kamara said, adding that her son woke up crying.
Meyers told the jury in the Crown’s opening address that a Toronto police plainclothes officer, who was involved in the arrest of Simon, is expected to testify.
Simon was arrested during a high-risk takedown around 8:30 pm on May 11, 2024, at a gas station in Orillia after travelling out of the city in a Nissan Maxima, which was being driven by the mother of one of Simon’s children.
The jury was told that they will hear evidence that a member of the team involved in the takedown found a handgun in a bag that had been at Simon’s feet in the car.
A firearms expert is also expected to testify that handgun recovered in the car was the same gun use to kill Roxburgh-Carpino.
Simon is also charged with occupying a motor vehicle knowing there was a prohibited firearm and possessing a loaded prohibited firearm.
He has also pleaded not guilty to those two counts.
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