The first Toronto Mayoral Debate is being moderated by an absolute buffoon
Jesse Brown? Are we fucking serious?
According to a press release issued today by the Jewish Lawyers of Canada, their organization will be hosting the first mayoral debate of the 2026 Toronto Municipal Election, on September 8th in front of a hand-picked audience of 1,200 people, specifically “to discuss public safety, antisemitism”, and other unenumerated issues. Most notably, the moderator of this debate will be none other than Jesse Brown, of Canadaland infamy.
If you’re unfamiliar with this notorious man, allow me to bring you up to speed. Coming into life-changing wealth after making millions of US dollars by selling a webcomic platform he was a partner in to Snapchat so they could turn it into an emoji generator, Mr. Brown used his financial boon to expand Canadaland, which prior to 2016 was a smaller, more humbly-sized media outlet, and initially in 2013 was simply his own one-man shop.
There’s nothing wrong with any of that. People have gotten wealthy from much less innocuous things than a webcomic creation tool, and if we’re going to criticize funding sources for media outlets, we should probably look at the minority stake which the Toronto Star owns in the NorthStar Bets online gambling platform. The problem with Mr. Brown is what purposes he’s used his power for, and aside from the genuinely good work he did in exposing Jian Ghomeshi, his output does not look positive.
Once upon a time, Canadaland hired good journalists who did important work. But ever since October 7th, Mr. Brown has found himself entirely captivated by the issue of Zionism, to the point of editorial interference with Canadaland’s journalists. The Canadaland Union released a public statement in December 2023 that “we are frustrated by Jesse Brown’s conduct and its impact on our work”, finally leading up to an incident in 2024, where Mr. Brown unilaterally edited a podcast hosted by journalist Justin Ling to remove fact-based statements because they were critical of Israel, resulted in a mass exodus of journalists from Canadaland, including the Editor-in-Chief Karyn Pugliese.
At least, the journalists with standards left. Canadaland’s reputation has increasingly gone down the shitter, as earlier this summer Mr. Brown and Canadaland were forced to settle a defamation case against Theresa Kielburger, acknowledging that his allegations that she had embezzled funds from the WE Organization were “unfounded” and “wholly retract[ing]” them. The total financial costs were over $800K Canadian Dollars, a settlement larger than what most courts have been awarding after trial for similar cases.
And from another angle, in April this year, Mr. Brown was banned from Reddit after attempting to ‘phish’, a term for a cyberattack where you are tricked into sending your personal information. Mr. Brown sent phishing links through the r/Canadaland Subreddit inside Direct Messages to Reddit users who criticized him, as well as through email to Mark Bourrie, a Canadian author, journalist, and a sworn member of the Ontario bar. Ms. Pugliese, Canadaland’s former Editor-in-Chief, also received one of these phishing emails, and PressProgress details in the piece above the names of many other Canadian journalists, considered to be in the “progressive” sphere of our national media, and who were targeted by phishing attempts at the same time.
While Mr. Brown initially denied links to those phishing attempts, he later claimed responsibility for sending it to Reddit accounts and Mr. Bourrie, but not to the other journalists. I leave it an exercise for the reader to theorize what his connection might be, if any, to the rest of phishing attempts that simultaneously occurred and followed the same pattern as the ones he’s confessed responsibility for. The important thing is that phishing violates Canada’s Criminal Code, and if he’s confessed to at least some of the phishing attempts, it raises questions why there have been no legal consequences.
With all this said, and with Mr. Brown’s explicit public statements that he does not accept any form of anti-Zionism and considers it indistinguishable from antisemitism towards all Jews—despite the growing segment of Canadian Jews who are explicitly anti-Zionist—it’s hard to believe Mr. Brown can be a fair moderator for a debate focused primarily on how the City of Toronto should respond to pro-Palestine protests, including whether it should be illegal to protest West Bank land auctions and speaking engagements with IDF soldiers that use our synagogues as human shields for odious political views. But worry not, Mr. Brown has spoken just a few hours before publication about this very issue, and his quote will truly make you guffaw:
“They say I won’t be impartial. They are correct.” Thanks, Mr. Brown, totally clears that issue right up! Absolutely doesn’t magnify concerns around whether this debate will be a good faith affair! Christ on a cracker, what a buffoon.
So far, right-wing candidates Brad Bradford and Chris Alexander have confirmed they will participate, but according to Jewish Lawyers of Canada, discussions are still “underway” with Mayor Olivia Chow as to whether the incumbent will also attend, and by her presence hand this farcical display legitimacy. I encourage the members of her campaign team, who I know follow my writing, to steer their candidate clear of this nonsense, lest it negatively impact her standing with the progressive voters she needs to keep happy.
Finally, on a personal note, Mr. Brown once criticized me on Twitter, implying I wasn’t “visibly Jewish” enough for him because I’ve worn a keffiyeh before. This rancid bullshit is not an acceptable way for Jews to treat each other, and I am well within my rights to reserve personal animosity for Mr. Brown.
But let me assure him, I have written this column impartially…so at least I’ve been more fair than he will be on September 8th.
Messrs Bradford and Alexander's respective participation in this farcical perversion of an electoral debate, when it is in fact designed to be a Zionism-advocacy event, is repugnant. I was previously disinclined to support either man but couldn't precisely identify the cause of my unease. Now I have my answer. Thank you.