Top5 evaded Ontario’s prison guards to shoot a music video: report

Jon Woodward reports on the allegations that Toronto rapper Top5 bribed a jail guard in order to release a music video from behind bars.

Ontario prison guards were furiously trying to seize the cellphone camera that Toronto rapper Top5 was using to record a music video in his cell, new documents obtained by CTV News Toronto reveal.

They stopped one phone from coming in that was smuggled in a visitor’s bra, and wondered if their own laptop cameras had somehow been repurposed as pictures of Top5, whose real name is Hassan Ali, kept surfacing online, an investigative report says.

In November 2022, guards strip-searched Ali but didn’t find anything, as the rapper, who was awaiting a murder trial, taunted them that they were “too late,” the document says.

“The inmate reportedly said the search was a week late, as he recorded himself eating cheeseburgers after receiving them from overnight correctional staff,” the report says.

“The inmate further stated that a music video would be posted via social media the following week and alleged that he utilized an iPhone 12 cellular device to capture the content before flushing it down the toilet.”

The video was posted not the following week, but about seven months later in June of 2023.

It showed Ali clearly behind prison walls at the Maplehurst Correctional Complex in Milton, Ont., rapping the song “21 Questions” while wearing orange jail-issue clothing.

Unauthorized photography is not permitted behind bars, and at the time, Ontario’s solicitor general, Michael Kerzner, vowed a full investigation.

After he beat the murder charge, Ali said in interviews that he had paid a prison guard $10,000 to bring in the phone.

But the investigation report, which was obtained via a freedom of information request and is heavily redacted, is silent on who that guard could have been and whether anyone was caught or punished for allowing the phone into Ali’s hands.

Kerzner, reached Wednesday at an unrelated news conference, couldn’t say either way whether anyone had been disciplined, and defended the guards, saying most do their jobs.

“99.9 per cent of everyone that keeps Ontario safe does just that. I don’t direct the ministry. This is an operational issue, but again, we will hold everyone to account,” he said.

Ali was cleared of murder charges in September 2024, after he was accused of being involved in the shooting of 20-year-old Hashim Omar Hashi, who police said was an innocent victim gunned down at his parking garage.

Ali spent time in California on the run, claiming his innocence over his social media account before he was arrested and returned the Canada.

In January 2025, Ali was arrested again, this time for charges including unauthorized possession of a firearm.

On Monday night, he was stabbed hours after attending a concert by fellow Canadian rapper Drake in the United Kingdom, police there said.

Hip hop media personality DJ Akademiks posted on his Instagram page that he had spoken with Ali, and he was injured but would recover.

“He has a big laceration,” he said. “It was kind of deep. He lost a lot of blood. He went through surgery. He’s going to have a full recovery, that’s a fact.”

Thousands of cellphones are smuggled into Canadian prisons every year, a recent W5 investigation found.

In the federal system, there were more than 2,700 seizures of cellphones or items related to cellphones in 2023-24, a 25 per cent climb from the previous year.

In Quebec, almost 2,000 cellphones were seized in 2023-2024, a number that has almost doubled since 2021-22.