Gambling Nation
In only two years, online betting has changed the face of Canadian sports. (Cover Story, Nov 2024)
Features
My latest features, investigations, and deep dives
The Battle for the Bay
The tangled story of the American real estate tycoon who stripped HBC for parts, the eccentric Chinese billionaire who lobbed a half-baked Hail Mary bid and the Canadian plutocrats who hatched their own backroom deal
“We met, fell in love and merged our families in a housing co-op. Now, we’re starting a co-op of our own”
Co-op housing is making a comeback. For all the potential friction of sharing a mortgage with your neighbours, it can be a beautiful thing. Jan Champagne and Miriam Zachariah met, fell in love and merged their families in a co-op. Now they’re founding their own
The Fight Over Forced Rehab
Canada’s nightmarish opioid crisis has renewed calls for involuntary drug treatment. Does the government have a right to force users to get help?
Game Over: Inside fallen Toronto Raptor Jontay Porter’s sports betting scandal
Jontay Porter may have been a Toronto Raptor, but as the pivotal member of a notorious betting ring, he was playing for another team. The story of a cheater, his bookmakers and the wager that brought them all down
Who Earns What: The stories behind Toronto’s top salaries
The stories behind Toronto’s top salaries
Rideshare drivers are fighting to unionize. One of Canada's biggest unions is standing in their way
Did UFCW sell out gig workers?
Antitrust Action Against Google May Transform the Internet
A global court and regulatory battle could have ramifications far beyond the news
Everything's Fine*
The ultimate guide to surviving every terrestrial threat imaginable (Cover story, April 2024)
What I Do
Hey there. My name is Anthony, and I'm a freelance journalist based in Toronto, Canada.
I'm a voracious generalist specializing in longform magazine writing. I've written feature stories on sports betting scams, forced drug treatment, the collapse of media and retail companies, efforts to unionize Uber drivers and anti-trust law, to name just a few. My work has appeared in Toronto Life, Maclean's, Ricochet, New Lines, The Trillium, TVO and more. Editors, I'm always open to assignments.
Over the year of 2025, I worked as an editor at Toronto Life magazine, and that same year I was nominated for Best Emerging Journalist at Canada's National Magazine Awards (in their words: “Anthony Milton is a writer of great depth.”) While on staff with Toronto Life, I conceived of and launched their successful weekly events newsletter, Front Row.
I hold a Master's of Journalism from Toronto Metropolitan University and a BA from the University of Toronto, specializing in philosophy and political science.
I'm always on the lookout for new story ideas and writing opportunities. You can find me on Twitter at @C_Anthony_Milton, or shoot me an email at charlesanthonymilton [at] gmail.com.
Keep scrolling to see more of my work.
Culture Writing
Highlights from my writing in Toronto Life's monthly culture section
“The culture and systems around hockey need to be better”: Rick Westhead on his new book, We Breed Lions
The reporter who broke the Hockey Canada sexual assault scandal talks toxic masculinity, team mentality and what can be done to save the soul of the sport
“If you want to kick Elon Musk in the dongle, aim for his margins”: Cory Doctorow on why the web went bad and how to fix it
The Toronto-born tech writer talks about the unifying theory of awfulness behind his new book, Enshittification
"Canadian comedy is some of the best in the world": Comedian Vic Michaelis wants to be a hometown kid
The very funny Very Important People star on flunking out of school in Toronto and how bingeing Survivor landed them a breakout role
“I was a goth in ’90s Toronto, and that scene inspires everything I write”: Mona Awad on her new novel, We Love You, Bunny
The author talks dark humour, being an outsider in the Ivy League and receiving the CanLit torch from Margaret Atwood
Oasis at Rogers Stadium, reviewed: "Wonderwall," bucket hats and light jabs from the Gallagher brothers
Plus a Squid Game–like exit from the venue
“The moment a writer starts a piece, they already know it’s a failure”: Miriam Toews on her new memoir, A Truce That Is Not Peace
The author of Women Talking talks small-town oppression, the search for reasons to write and what motivated her first foray into the memoir genre
“I never had a nuanced explanation of sexual assault growing up”: Hannah Moscovitch on her new play, Red Like Fruit
The playwright talks straddling the Canada–US border, working with Hugh Jackman and coming to terms with childhood trauma
"Toronto is my obsession": André Alexis on his new short story collection, Other Worlds
The author talks about honouring his parents through writing, the beauty of his adopted home and what it means to behave “Canadian”
"Success is random—all you can do is keep improving": Max Kerman of Arkells on his new memoir, Try Hard
The indie rock frontman talks growing up downtown, the changing nature of the music business and the inspiration behind his first book
Omar El Akkad on his new book about Palestine, Israel and Western hypocrisy
In One Day, Everyone Will Have Always Been Against This, the author and journalist presents a scathing account of news media and governments cheering on the genocide in Gaza
Charlotte Day Wilson on her new album, Cyan Blue
The R&B singer discusses the city’s signature sound, her skating skills and collaborating with artists like Badbadnotgood and Daniel Caesar
"You have to become Alice—the audience knows if you're faking it"
A Q&A with Tirion Law, lead ballerina in Alice’s Adventures in Wonderland
Interviews
Straight question-and-answer style stories
"It's like hiring an army of sloths": Councillor Josh Matlow on the city's excruciatingly slow snow removal
The councillor for Toronto–St. Paul’s discusses his ire over Toronto’s $1.5-billion privatized snow plows, what we could learn from Montreal and his personal shovelling saga
New chief planner Jason Thorne on his grand designs
After a decade in Hamilton, Thorne has been selected as our planner in chief. With traffic in gridlock, transit ever-delayed and housing far from affordable, he’s got his work cut out for him
This LGBTQ immigration lawyer has been inundated with inquiries from the US since Donald Trump's election - Toronto Life
President Trump has launched an attack on the rights of trans people in the United States. Could Canada become a safe haven for American refugees?
"The rest of the country is waking up to what First Nations people have always known"
Tanya Talaga on her new book, The Knowing
“The voices of refugee claimants will be critical”: Meet Toronto’s new deputy ombudsman for housing
Reema Patel is taking up the brand-new mantle of housing watchdog. Her first task: investigating the city’s decision to turn asylum seekers away from shelters
"Some of my skate friends are 10 and some are 50": Meet 13-year-old skateboarding phenom Fay DeFazio Ebert
Fresh off her gold medal win at the Pan Am Games, Ebert talks good luck charms, the best bowls in Toronto and setting her sights on Paris 2024
"It can be a struggle to get health care": Filmmaker M. H. Murray on bringing the realities of HIV treatment to TIFF
Murray’s debut feature film, I Don’t Know Who You Are, follows a Toronto artist scraping together money for preventative treatment after being sexually assaulted
"Being budget chief is an honour—but there's also a sense of dread": A Q&A with Councillor Shelley Carroll
Toronto’s newly appointed fiscal czar dishes on why the city needs new taxes, playing hardball with Queen’s Park and Ottawa, and how her grandkids keep her grounded in a chaotic time
Everything
The Battle for the Bay
The tangled story of the American real estate tycoon who stripped HBC for parts, the eccentric Chinese billionaire who lobbed a half-baked Hail Mary bid and the Canadian plutocrats who hatched their own backroom deal
“A stainless steel mirror finish captures infinity”: Metalworker Ranbir Sidhu on his new AGO exhibition
The artist, whose work is collected by Drake, will debut a two-tonne sculpture at the gallery this month
“The culture and systems around hockey need to be better”: Rick Westhead on his new book, We Breed Lions
The reporter who broke the Hockey Canada sexual assault scandal talks toxic masculinity, team mentality and what can be done to save the soul of the sport
A timeline of the most outrageous moments from Tom Green’s legendary career
The revered and reviled shock comic has a new documentary, a new stand-up special, a new reality show and a new Canadian tour. Here are the ill-advised stunts that got him where he is today
These paintings being auctioned off by the Hudson's Bay Company will incite bidding wars
Forget the striped blankets—these are the truly valuable pieces of Canadian history
“If you want to kick Elon Musk in the dongle, aim for his margins”: Cory Doctorow on why the web went bad and how to fix it
The Toronto-born tech writer talks about the unifying theory of awfulness behind his new book, Enshittification
“We met, fell in love and merged our families in a housing co-op. Now, we’re starting a co-op of our own”
Co-op housing is making a comeback. For all the potential friction of sharing a mortgage with your neighbours, it can be a beautiful thing. Jan Champagne and Miriam Zachariah met, fell in love and merged their families in a co-op. Now they’re founding their own
"Canadian comedy is some of the best in the world": Comedian Vic Michaelis wants to be a hometown kid
The very funny Very Important People star on flunking out of school in Toronto and how bingeing Survivor landed them a breakout role
“I was a goth in ’90s Toronto, and that scene inspires everything I write”: Mona Awad on her new novel, We Love You, Bunny
The author talks dark humour, being an outsider in the Ivy League and receiving the CanLit torch from Margaret Atwood
TIFF’s most controversial film had its first—and only—screening on Wednesday
Filmmaker Barry Avrich’s October 7 documentary, The Road Between Us, premiered amid protests, a heavy security presence and the booing of Q&A host Lisa LaFlamme
What to see, do, read and hear in Toronto this September
Featuring oil-painting remixes of classic works of art, a street festival bursting with community vibes, and a provocative off-Broadway hit about interracial love and lust
Oasis at Rogers Stadium, reviewed: "Wonderwall," bucket hats and light jabs from the Gallagher brothers
Plus a Squid Game–like exit from the venue
“The moment a writer starts a piece, they already know it’s a failure”: Miriam Toews on her new memoir, A Truce That Is Not Peace
The author of Women Talking talks small-town oppression, the search for reasons to write and what motivated her first foray into the memoir genre
What to see, do, read and hear in Toronto this August
Including an open-air performance of a doomed romance and a hotly anticipated reunion tour
Who's to blame for Masai Ujiri's ousting?
Spicy theories swirling around the Raptors president’s sudden departure
The Best of the Fests: What to see, do and hear in Toronto this festival season
It’s festival season, and the streets are brimming with music, art, theatre and other forms of summer revelry. Here, a roundup of the best bets of the month
Josh Matlow dreams of a Toronto without piles of hot garbage. Can it be done?
The city councillor sounds off on overflowing trash bins and why the current privatized maintenance contract is rubbish
Inside goth icon Beetlejuice’s journey from screen to stage
A new Mirvish production is reanimating the 1988 cult film
What to see, do, read and hear in Toronto this June - Toronto Life
1 The title of this 50-year retrospective of legendary artist Joyce Wieland’s work, Heart On, aptly reflects her propensity for cheek. Born and raised in Toronto, Wieland worked as a graphic artist and filmmaker before moving to New York, where she discovered quilt-making. She returned home in 1971 because she couldn’t abide America’s war in Vietnam, and that same year she became the first woman to exhibit at the National Gallery of Canada. Her oeuvre celebrates the north and deals with the them...
"The sad truth is that Kensington Market isn't healthy anymore": Why this neighbourhood fishmonger is closing up shop
Kristin Donovan, co-owner of Hooked, on leaving a neighbourhood she loves
For a cool $1,700, let your inner F1 driver loose at Porsche's new racetrack in Pickering - Toronto Life
Got several hundred dollars and a need for speed? Wondering why cars have hundreds of horsepower just to inch along, slower than bikes, in gridlocked Toronto traffic? Then rejoice, for Porsche is opening a brand-new two-kilometre-long test-driving track in Pickering, complete with tight turns and screaming straightaways to zip down. You know, the stuff cars were made to do.Related: Three Torontonians who retrofitted their vintage cars for the electric ageFor $1,700, would-be F1 drivers can hop i...
The Fight Over Forced Rehab
Canada’s nightmarish opioid crisis has renewed calls for involuntary drug treatment. Does the government have a right to force users to get help?
“I never had a nuanced explanation of sexual assault growing up”: Hannah Moscovitch on her new play, Red Like Fruit
The playwright talks straddling the Canada–US border, working with Hugh Jackman and coming to terms with childhood trauma
A bridge, a tunnel, a gondola—all the ways the city may connect the Toronto Islands to the mainland
Expensive ideas to help more people let loose at the beach
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Contact Me
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