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Sidewalk essays
City News
Toronto is surveillance capitalism’s new frontier
The city of Toronto now sits in the crosshairs of a uniquely 21st-century economic model that I call surveillance...
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City News
How the Sidewalk Labs proposal landed in Toronto: the backstory
In 2001, when Waterfront Toronto was formed, Mel Lastman was in the waning days of his mayoralty, Vince Carter was the heart of...
City News
Sidewalk Labs is the future of urban tech
A dozen or so years ago, I was recruited to Toronto to establish the Martin Prosperity Institute, a think tank focused on...
City News
A smart city should serve its users, not mine their data
The concept of the “Internet of things” refers to the spread of Internet connectivity to everyday devices:...
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City News
Sidewalk Labs will attract and retain tech talent
At the Toronto Region Board of Trade, one of the stranger questions we’ve been asked is why we would support a U.S. firm like...
City News
Sidewalk needs to integrate with the waterfront
When I chaired Waterfront Toronto’s design review panel from 2005 to 2017, our goal was to create continuity. Today, a promenade...
City News
A big city needs to take big risks
Imagine if the Raptors had kept DeMar DeRozan in 2018. Imagine if fans, sponsors and pundits all saw trading for an injured Kawhi...
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City News
The Sidewalk Labs deal is unconstitutional
Once upon a time, some unelected folks at Waterfront Toronto blurted out, “Hey Google, what’s the best way to develop...
City News
Toronto needs to maintain control of its transit planning
In the summer of 1972, Toronto east-enders had had enough. The Toronto Transit Commission wouldn’t hear their petition for a new...
City News
Sidewalk is our last chance to save the waterfront
Toronto’s Port Lands are the last big opportunity for the city’s lakefront. It’s a huge area, almost as big as downtown, but...
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City News
Sidewalk’s affordable housing isn’t really affordable
Sidewalk’s proposal for Toronto’s eastern waterfront has a few foundational promises: first, that this Google company can...
City News
Toronto can create a new model of urban development
Cities are the sum of choices we’ve made over decades and centuries. New chapters in a city’s history often begin with a...
City News
Corporations should not be controlling our city-building
Remember when Uber started? The story was innovation: the jobs, the convenience, the new tech sector. Now, 10 years later, the...
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City News
De-identifying data at the source is the only way Sidewalk can work
When Sidewalk Labs first approached me to be a consultant three years ago, I told them that if they hired me, I’d be happy to...
City News
We can harness the private sector for the public good
Toronto is on a roll, emerging as one of the world’s best cities. We’ve never been better or more vibrant. Economic and...
City News
Sidewalk Labs is Toronto’s best hope for sustainability
The Maori say we walk backwards into the future: we are so focused on our past that we do not properly experience the present, so...
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City News
Toronto needs exciting new architecture
In 2017, Sidewalk Labs approached PARTISANS to design facade and public-realm architecture for Quayside. Like most Torontonians, I...
City News
Sidewalk needs to work with Toronto’s tech ecosystem
Toronto is not only the fastest-growing city in Canada and the U.S., but also the fastest-growing technology hub. All three levels...
City News
The Quayside project is a gift to Toronto’s public realm
In recent decades, Toronto has become a remarkably heterogenous city, with more than half of its residents born in another...
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Private School Guide
The Private and Independent School Directory Spring 2025
Big Stories
Deep Dives
Dancing Queens: Patrons, staff and performers share their wildest memories of Crews and Tangos, Toronto’s most storied drag bar
Crews and Tangos has been enforcing the rules of the Village for more than 30 years: wear what you want, kiss who you want, but don’t forget to tip the drag queens. With a condo development looming, we asked around for tales from the iconic spot
Deep Dives
The Joy of Sex with Strangers: A Toronto hotwife’s adventures in ethical non-monogamy
Three months ago, I was a suburban mom in a monogamous relationship. Now I’m sleeping with people I meet online—with my husband’s blessing—and we’ve never been happier. Don’t judge us until you’ve read our story
Deep Dives
The Scandal, the Firing and the Fallout: Anatomy of a Bay Street fiasco at RBC
Nadine Ahn was a high-ranking executive at the bank. Ken Mason, her subordinate, was rapidly promoted. Then someone claimed to see them canoodling at the Royal York, tipped off HR and triggered an inquisition
Deep Dives
Edward the Conqueror: The unlikely ascent of Canada’s telecom king
Edward Rogers was dismissed as a meddling nepo baby—until he muscled out his siblings, acquired his competitors, cornered the telecom market and became the dominant force in Canadian sports
Deep Dives
Lady Parts: Inside Meredith MacNeill and Jennifer Whalen’s new show,
Small Achievable Goals
The
Baroness von Sketch Show
alumnae have elevated joking about women’s issues to an art. Their new show takes aim at menopause. How funny is that?
Deep Dives
Murder in the Blue Mountains: The story behind the killing of Ashley Schwalm
Ashley and James Schwalm had what seemed like a fairy tale life—two wonderful children, fulfilling careers and a gorgeous home close to the private ski club where they’d fallen in love. Then Ashley’s remains turned up in a burned-out car at the bottom of a ditch, and all signs pointed to her husband
Deep Dives
Dark Horse: Inside the fall of Eric Lamaze, Canada’s most famous equestrian
For years, Lamaze was the world’s top-ranked show jumper, living an enviable life filled with fancy cars, international travel and adoring fans—the kind of life a person might do anything to protect
Deep Dives
Dividing Line: How the Bloor Street bike lane turned the city into a battlefield
A few kilometres along Bloor has become Toronto’s most contested strip of concrete, igniting fights over congestion, safety and the future of downtown
Deep Dives
The Chosen One: At just 23, Scottie Barnes is the new face of the Raptors—and the team’s best chance of salvation
Barnes is shouldering the weight of an impatient, basketball-mad city, a hit-and-miss team, and his own colossal ambitions. Does he look worried?
Deep Dives
Almost
Famous: Inside the Beaches’ rise to rock stardom
A viral earworm about a breakup turned the Beaches into Toronto’s hottest export. Now, the panty-throwing, stage-diving, all-girl rock band is seducing fans around the world
Deep Dives
“I was nearly beaten to death by my partner. The case was dismissed because it took too long to get to trial”
How an overburdened justice system is failing survivors of intimate partner violence
Deep Dives
Brave New Year: The ultimate try-anything-once bucket list for 2025
For inspiration on wonderful, wild and even some slightly reckless experiences to enjoy in the year ahead
Deep Dives
The stars of the PWHL’s Toronto Sceptres on finally having a league of their own
After kicking off a new chapter for hockey with the PWHL, Natalie Spooner, Sarah Nurse and Blayre Turnbull are blazing a trail for women in sports
Deep Dives
The 50 Most Influential Torontonians of 2024
Our annual ranking of the people whose courage, smarts and clout are changing the world as we know it
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Food & Drink
The US tariffs are coming for your espresso martini
With Kahlúa no longer available at the LCBO, Toronto bartenders are getting creative
Food & Drink
These Ontario-made booze collaborations are coming to a restaurant near you
Toronto bars and restaurants are partnering with their favourite distillers, winemakers and brewers to produce custom-made drinks. Here, nine crushable new concoctions
Food & Drink
“We have over 100 cases of American wine trapped at the LCBO”: Toronto’s Grape Witches on what it’s like to run a bottle shop during a trade war
It’s not as simple as taking sides when you’re a small business
Food & Drink
Six Toronto restaurants serving up all-Canadian menus
With a trade war upon us, our city’s chefs are taking a stand