Open this photo in gallery:

Protestors for Gaza gather outside a downtown hotel in Toronto, the planned location of an event for Prime Minister Justin Trudeau on March 15, 2024. According to experts, the Toronto Police’s allegations against Mr. Hajahmad are potentially novel because they stem from words he said during a protest, which police say furthered the interests of Hamas.Cole Burston/The Canadian Press

A man charged by Toronto Police with a terrorism offence over his alleged conduct at pro-Palestinian rallies has previously been at the centre of the debate around acceptable expression at protests, after a photograph of him from two years ago prompted criticism from federal politicians – and led to multiple libel lawsuits.

Ahmad Hassan Hajahmad, 33, was arrested Tuesday and charged with participating in or contributing to the activities of Hamas, in what is believed to be a potentially groundbreaking use of Canada’s Anti-Terrorism Act. Toronto Police said they gathered evidence after his appearances at two demonstrations in May and September of 2024 supporting the allegation that he acted in association with the designated terrorist group.

Charge sheets filed in Ontario Superior Court do not provide additional information on what Mr. Hajahmad allegedly said at the protests that led police to investigate him. His lawyer has denied the allegations, which have not been tested in court.

Separate from the charge, Mr. Hajahmad was the subject of controversy after a widely circulated photo showed him at a 2024 Al-Quds Day rally.

The Al-Quds Day rally is an annual pro-Palestinian event that has frequently been criticized. Earlier this year, Ontario Premier Doug Ford attempted to block the rally, arguing it was a “breeding ground for hate and antisemitism.” But organizers denied this, and civil liberties groups expressed concerns about trampling people’s rights to protest.

The 2024 rally in Toronto happened less than a year after Hamas’s deadly Oct. 7, 2023, attack on Israel, which was followed by Israel’s invasion of Gaza. Subsequent demonstrations in support of the Palestinian people have triggered heated debate about the limits of public discourse and free speech because they often include intense denouncements of Israel that critics say cross the line into antisemitism.

The photo of Mr. Hajahmad at the 2024 rally showed him wearing what appeared to be a belt strapped over his chest containing canisters fitted with pull rings. In an e-mail, Mohamed El Rashidy, Mr. Hajahmad’s lawyer, told The Globe and Mail that his client was wearing an Enola Gaye Hang Ten Belt. The belt is a device used to hold smoke grenades for paintball or airsoft, according to the company’s website.

The photo of Mr. Hajahmad was shared widely on social media and elicited a strong reaction.

At the time, Conservative deputy leader Melissa Lantsman, in a social media post, described the device as a “pretend suicide vest.” Former independent MP Kevin Vuong likewise called it a “mock suicide vest,” and B’nai Brith Canada, a Jewish advocacy group, posted a video containing the photo of Mr. Hajahmad with a caption calling the event a “hate-filled” rally.

The photo was also the subject of a video and column by Toronto Sun columnist Brian Lilley, who called Mr. Hajahmad’s garb a “replica suicide vest.”

In July, 2024, Mr. Hajahmad sued Mr. Lilley and the Sun’s owner, Postmedia Network, for $35,000 in damages. Later, in November 2025, Mr. Hajahmad filed a libel suit against Ms. Lantsman, Mr. Vuong and B’nai Brith Canada seeking $18,500.

Mr. Hajahmad, in his statements of claim, says he is Palestinian by origin and describes himself as a recognizable individual in the Palestinian solidarity movement. Mr. El Rashidy, his lawyer, said the allegations his client was wearing a fake suicide bomber vest “are completely false.”

Both lawsuits say the criticisms of him were defamatory and intended to “lower him in the estimation of others in the broader community,” and expose him to hatred, contempt or ridicule. His statements of claim also say the posts and writings imply he was engaging in activities that were either criminal, terrorist, violent, racist, or intended to harm Jewish people.

Mr. El Rashidy has defended his client against the Toronto Police’s accusation that Mr. Hajahmad acted on behalf of Hamas.

“He faces a single charge arising from speaking at public demonstrations. No violence, no weapon, no one harmed,” he wrote in a statement this week. “Speaking out at a protest about the killing of civilians is protected expression, not terrorism.”

Mr. Hajahmad was charged in 2025 with mischief after Toronto Police accused him of discharging a smoke canister inside Union Station. His charge was eventually withdrawn and he was given a peace bond, Mr. El Rashidy said.

Robert Karrass, who represents Ms. Lantsman, said in an interview that Mr. Hajahmad’s vest was “clearly meant to portray some sort of militant, violent thing.”

“I think my client is quite vindicated by this because it just goes to show that he’s been charged with something substantially worse than anything that my client suggested,” he said, referencing the charge laid against Mr. Hajahmad on Tuesday.

Ms. Lantsman’s statement of claim says the previous mischief charge against Mr. Hajahmad confirms and reinforces that her social media post “was one of legitimate public safety concern.”

The lawsuit against his client and the other parties is scheduled for a settlement conference in October, Mr. Karrass said.

B’nai Brith Canada will continue to defend itself “vigorously” against the claim, spokesperson Jonah Fried said in an e-mail.

He said the recent terrorism allegations and charge against Mr. Hajahmad are alarming.

Mr. Lilley’s lawyer, Brendan Hughes, declined to comment on the lawsuit.

Mr. Vuong and his lawyer, Mark Donald, did not respond to a request for comment.

Mr. Hajahmad appeared in court on Tuesday after his arrest and was released on bail for $50,000, according to court documents. He was ordered to live in Mississauga with his surety. His bail conditions include a ban from being in Toronto and from engaging in demonstration-related activity within 500 metres of synagogues or Jewish community and cultural centres.

According to experts, the Toronto Police’s allegations against Mr. Hajahmad are potentially novel because they stem from words he said during a protest, which police say furthered the interests of Hamas. That connection will be key to determining whether the charges stand up in court, they say.

Mr. Hajahmad’s charge carries a penalty of up to 10 years in prison.

Toronto is among many cities that have wrestled with the thorny issue of regulating protests in response to demonstrations against Israel’s war in Gaza in the aftermath of the Oct. 7, 2023, attacks.

In May 2025, Toronto joined a growing list of Canadian cities, including Calgary, Brampton and Vaughan, that passed controversial “bubble zone” bylaws. Toronto’s regulations created a 50-metre buffer zone to restrict protests near some schools, daycares and places of worship. Violators can receive a maximum $5,000 penalty.

While terrorism investigations typically fall to the RCMP’s federal policing mandate, Toronto Police in March announced a new counterterrorism unit as part of its response to violence linked to the Middle East conflict.

The federal Liberal government also recently passed an anti-hate bill that makes it a crime punishable by up to 10 years in prison to obstruct someone from accessing a place of worship or other sites where Jews, Muslims and other identifiable groups gather. That law came into force on July 18.