Controversial Chris Sky declares his candidacy for Toronto mayor amidst scandal and scrutiny

Democracy has valleys and peaks. Somehow, this is both.

Toronto has a long and time-honoured tradition of unlikely candidates in municipal races, particularly those vying for the top spot.

It does not take much to run for mayor in North America’s fourth largest city. There are qualification requirements based on age, citizenship, and not being legally prohibited from voting or holding municipal office. Candidacy is open to Toronto residents, owners and tenants within the city, and the spouses of owners and tenants.

The filing process is simple, involving a nomination form, 25 endorsements with original signatures, a piece of identification, and the $200 filing fee.

In related news, Chris Sky is officially running for mayor.

Chris Sky addresses media after submitting nomination forms on April 3, 2023.

The most recent municipal election occurred in October 2022. Incumbent mayor John Tory was easily re-elected to a third term. Tory had been an ideal foil to the shenanigans and exploits of previous mayor—and international joke—Rob Ford. In contrast to Ford’s uninhibited and chaotic public image, Tory built his reputation on appearing strait-laced and sensible. He assumed an almost fatherly persona during the pandemic, gently yet sternly chiding residents about making better choices.

Turns out “Toronto’s dad” may have been more of a daddy. In early February 2023, Tory revealed that he carried on an affair with a staffer while the city was in lockdown. He abruptly resigned, thus triggering a mayoral by-election.

Enter the circus.               

Chris Sky is most widely known for his anti-government views. He rose to notoriety after being interviewed by Ed the Sock at an anti-mask rally. During the height of lockdowns, he advertised and attended parties at Cherry Beach. A viral video of “maskless shopping” featured him storming into Longo’s, grabbing a bottle of maple syrup from the shelf, and tossing $20 at the hapless grocery store clerk. He livestreamed himself defying temporary quarantine measures at airports. After his name was added to the no-fly list, he drove across the country in a white Range Rover (and later an RV) to spout conspiracy theories at rallies and sell merchandise out of garbage bags. He boasts about being arrested 26 times.

Former crew members have come forward about Chris Sky’s verbal and physical abuse. He has been condemned for espousing racist and intolerant views. There are also serious questions about his collection of donations for ventures that never fully materialize, including a mask-free private school, litigation fundraising on behalf of police (which police squarely denied), NFTs on the Ethereum blockchain, a social media website, and more.

Prior to the pandemic, Chris Sky was a playboy who lived out his lavish lifestyle on Instagram. The son of wealthy Vaughan developer Art Saccoccia, he appeared to spend his time lifting weights, hinting at orgies, and grooving in exotic destinations.

Municipal politics is significant because it represents the level of government that is closest to the community and directly impacts people's lives on a day-to-day basis. There are real, existential issues facing Torontonians, including rampant poverty, crumbling infrastructure, and random acts of violence on public transit.

It is a feature of democracy that nearly anyone can run for office, including ne’er-do-wells. Chris Sky is a controversial and questionable figure with no political experience who has yet to demonstrate his grasp on local matters. His bid for mayorship is easily dismissed as a gimmick— and yet, Sky’s confused and conspiratorial rhetoric seems to resonate with supporters.

Freedom of the press and access to information enables voters to scrutinize candidates and their platforms. In an effort to promote informed decision-making, this series will expose the real Chris Sky.