A Communist Spy On Bay Street
Plus a new book from Spacing, a new statue at Queen's Park, and more...
Bay Street. It's synonymous with capitalism in Canada. A canyon lined with skyscrapers that stand as monuments to profit and private property, titanic monoliths filled with banks, law firms, corporate headquarters and stock brokerages. Many of them have been there for more than a century, but in the 1960s new towers of glass and steel were sent soaring into the sky. Toronto was becoming the heart of Canadian finance. And at that very moment, at the corner of Temperance Street, in an unassuming mid-century mid-rise, a secret agent was preparing to strike a blow against it all. Hidden among the bankers, lawyers and stockbrokers was a woman plotting a mission to seduce some of the most powerful political figures on the continent. In 1968, there was a Communist spy lurking on Bay Street.
Her name was Jennifer Miles. She was born and raised in South Africa, but at the age of twenty she and a couple of friends set off on a trip to see the world. It took them across Europe and eventually to Canada. It was in Toronto that Miles decided to make her new home.
She arrived at the beginning of 1965, getting a job as a secretary at a big brokerage firm on King Street. She'd later be remembered for her friendliness and work ethic. She spent her nights studying to become a qualified stockbroker, learned bookkeeping, and was soon promoted, becoming the private secretary to the company's director.
But all the while, she also seems to have been gaining valuable experience of another kind. There, among the misogynist Mad Men-ish skyscrapers of the 1960s financial district, she honed the skills she would later put to use as a secret agent. She was young, attractive and outgoing, with what her boss called a "sparkling personality." Reports invariably describe how popular she was with the men of the firm in particular. "Everybody knew Jennifer — you couldn't miss her," one former colleague told The Globe and Mail. "She was liked, because she was, well, flattering to men."
They say it was an STD that changed the course of her life. In the spring of 1967, with the sexual revolution underway and the Summer of Love about to begin, she fell ill with a case of hepatitis. It left her bedridden, and during her long recovery she had plenty of time to read. That's when she began to devour newspaper reports about what had been happening in Cuba, stories about Che Guevara and Fidel Castro and their Communist revolution.
Miles was hooked. Her boss once explained that she was often caught up in "any little cause that would turn her on… anything she thought was being oppressed." And no other cause ever captured her imagination like the Cuban Revolution. "She saw Cuba as a romantic, sunny island," journalist John Barron once wrote, "being transformed into a utopia by dashing, brave men of vision."
She joined the Canadian branch of the Fair Play for Cuba Committee, volunteering her time and energy to the cause; the high-profile activist organization had attracted the support of everyone from Norman Mailer, James Baldwin and Truman Capote to Jean-Paul Sartre and Simone de Beauvoir — and, most infamously, the assassin Lee Harvey Oswald. The more she learned, the more she became determined to visit Cuba herself.
It wouldn’t be easy. Visas were hard to come by. You had to travea Mexico. But the charm Miles was known for in the financial district would prove to be very useful. As Barron put it, "When she chose, she could make her blue eyes and shy smile combine to convey an unspoken invitation no man could mistake. She could evaluate a man quickly and intuitively, then fashion an individualized approach that suggested she was powerless to resist him… She created about herself an aura of innocent vulnerability. No one felt threatened by her, and everyone wished to help."
In Mexico City she charmed a stranger into helping her pretend to be an anthropologist studying Indigenous cultures in order to get her visa, charmed another man she met on the plane to give her a drive to a hotel in Havana, and then charmed the fully-booked hotel into giving her a room. Soon, her face was being broadcast on Cuban television, picked out of a crowd watching Castro give a speech on the anniversary of the revolution. That caught the attention of the regime.
The Cuban authorities saw an opportunity. She was given a tour of the island by a government escort, a free hotel room, and the chance to become directly involved in the cause, working long hours in the fields harvesting crops. She fell in love with the country. Even the hardships of life under Castro were inspiring to her; she took them as proof people were willing to sacrifice for the common good.
"I was young, adventurous and idealistic at the time…" she later explained. "Overseas, politics takes on a whole new and exciting meaning and girls can be attracted by leaders who appear bright and charismatic and seemingly romantic."
And so, Miles was recruited as a spy. She became a secret agent for the Dirección General de Inteligencia — the Cuban government's intelligence agency.
When she returned to Toronto, she pretended as if nothing had happened. She didn't talk much about her trip. She played down her interest in Communism and stopped volunteering for the Fair Play for Cuba Committee. That's when she began working in the building on the corner of Temperance and Bay Street, getting a job with another big brokerage firm. But she also began quietly looking for a new position: something that would take her to Washington, D.C. All the while, she gave her Cuban handler updates on her job search by travelling to Montreal and leaving secret messages in an alleyway near McGill University.
Soon, there was good news. By the end of 1968, Miles had left Toronto to begin her mission in the American capital. She'd been sent to infiltrate Washington's social scene, to use her seductive skills to operate a honey trap.
She started by temping as a typist at the South African embassy, but quickly turned that into a permanent position. She got a nice apartment just a short drive from the White House, stocked it with booze, and began entertaining. She joined a social club as a way to meet young foreign diplomats who would then invite her to parties where she could meet the American officials she was there to seduce. She's said to have begun sleeping with a series of well-positioned men, gradually working her way up the echelons of power in search of valuable secrets.
There are conflicting reports about just how useful that information was to the Cubans. While some suggest she was able to get her hands on blueprints of American ships and submarines, others claim her contribution was limited to compiling details about the personal lives of U.S. officials. And it could very well be that Miles' mission was more about a long-term plan to win the heart of a powerful diplomat or politician, putting her in a position to be gathering intelligence for years, maybe even decades to come.
But whatever secrets she was handing over, she was certainly having enough success that it left the Americans deeply concerned. They'd been watching her for a while.
It was a stroke of remarkably bad luck that first tipped them off. Miles was still giving regular updates to her handler, travelling from D.C. to New York City, where she left her messages in a little brick wall next to an apartment building in Queens. There were some flowers planted atop that wall, and one day, as the superintendent was trimming them, he dropped his shears. When he bent down to pick them up, he noticed the tiny cylindrical package she'd left inside the crack. Once he got it open and read the suspicious messages inside, he called the FBI.
The agency only needed one day to figure out who she was. There were enough details in her messages for them to piece it together. They got the call on Sunday morning and by Monday night, Jennifer Miles was under surveillance. They would follow her for the next year. All through the winter of 1969 and the summer of 1970, the Americans watched her bringing men back to her apartment, more than a hundred in total, and listened to her through the bugs they'd planted inside. Month by month, those men were becoming more and more important, and the FBI was beginning to worry. At first, they'd been hoping she would lead them to high-ranking members of the Cuban intelligence agency, maybe even the KGB. But she was soon getting so close to real power in D.C. that they decided they needed to pull the plug.
In the fall of 1970, she was called into the office of a diplomat at the South African embassy where she worked. He asked her to deliver an envelope to a nearby hotel room. When she arrived and knocked on the door, she found the FBI waiting for her.
At first, she denied everything. "This is very thrilling," she told them, "but I'm rather afraid you've confused me with someone else." It wasn't until they showed her the message she'd left in New York and photos they'd taken of one of her meetings with her handler that she realized it was a lost cause. "I will do nothing to hurt Cuba," she insisted, but soon offered to confess.
When the story broke, it was big news back in Toronto, where she'd spent those years working among the bank towers of Bay Street. The local press interviewed her former co-workers and employers, trying to understand how the friendly secretary had become a notorious spy. And since it was all revealed in the fall of 1970 — the same autumn as the October Crisis — she was even suspected of having ties to the separatist terrorists of the FLQ.
Others imagined she might have been a double agent for another agency altogether. Miles was never charged for her espionage. Instead, she was allowed to return home to South Africa in exchange for a promise she would never visit the United States again. That raised eyebrows. At least one author has wondered whether she might have been secretly working for the apartheid government of South Africa all along. And when a Johannesburg newspaper tracked her down, she gave them no comment other than to suggest they ask the head of the apartheid intelligence agency about it instead.
For a while, Miles continued ducking the media. She got a job as a secretary at a carpet company and then briefly disappeared. In the years to come, she denied the most salacious reports. When the journalist John Barron wrote his book about spies, including a chapter about Miles, she tried to block it from being published, denouncing it as being filled with defamatory lies.
But she would also capitalize on her newfound notoriety. Just weeks after leaving the United States, she began writing a newspaper column about sex and gossip for South Africa's Sunday Times — it was framed as being written by "our blonde spy." She would later appear in furniture commercials, advertising a sofa bed named after a musical inspired by the story of Mata Hari, the notoriously seductive German spy. And she showed up on the cover of a controversial men's magazine in a swimsuit, holding a gun, clearly playing with her reputation as a secret agent.
After that, her life seems to have grown much quieter. She soon married an engineer from Cape Town and decided to leave South Africa behind once again. The new couple set out for Toronto, returning to the city where it all began.
In the decades since, her story has been retold from time to time, by writers, authors and journalists. And every once in a while, one of them tries to ask her about those old days of the Cold War and her secret mission to Washington. But it seems we'll never know the truth of it all. She's always stuck to what she told those reporters back in South Africa when the news first broke:
"My story," she said, "will go to the grave with me."
I first stumbled across the story of Jennifer Miles in The Globe and Mail this summer while reading old articles about the October Crisis. You’ll find John Barron’s book about Cold War spies — “KGB: The Secret Work of Soviet Secret Agents” — at the Internet Archive here. Miles is also included very briefly in Pamela Kessler’s “Undercover Washington: Where Famous Spies Lived, Worked, and Loved” (it’s on Google Books here). And her story also appears in “Betrayal: The Secret Lives of Apartheid Spies” by Jonathan Ancer, who is the writer who suggests Miles may have beeen working for the South African intelligence agency, BOSS.
One source suggests Jennifer Miles even hosted a TV program in Toronto in the 1990s — though I haven’t been able to find any more information about that. If you know what show it was, definitely let me know!
I’ve Got A Story In The Big Book of Spacing!
Last weekend, Spacing celebrated their 20th anniversary with a big birthday bash — and it doubled as a launch party for a new book compiling some of the stories they’ve published over the last two decades. As they put it, The Big Book of Spacing is filled with “the best content from our magazine, website, and books from the last 20 years [which] trace both our magazine’s and city’s evolution.”
I can’t thank everyone at Spacing enough for all the support they’ve given my work over the years, starting when they first invited me to share my blogposts on their site all the way back in 2012. Those were still very much the early days of my writing about Toronto history and it was a huge encouragement, an amazing boost that became one of the big falling dominoes leading to the creation of this newsletter.
I shared nearly 100 posts on Spacing over five years, but my most popular piece was the second one I ever published on the site: the story of the Circus Riot and how it was sparked by a brawl at a brothel between clowns and firefighters back in the summer of 1855. That’s the piece they’ve included in the book…
You can grab The Big Book of Spacing from the Spacing Store at 401 Richmond — and visit the Toronto sports history exhibit I’ve co-curated for Myseum while you’re there (it’s right across the hall)! Or you can buy the book online here.
The Toronto History Weekly only exists thanks to those of you wonderful people who are willing to support it with a few dollars a month. Thank you all so much! If you haven’t made the switch to a paid subscription yet but would like to, all you have to do is click the button below. Only about 4% of readers have made the switch so far, which basically means that with your subscription, you’ll be giving the gift of Toronto history to 25 other people:
Give The Gift Of Toronto History!
Speaking of gifts… Just in case you’re still looking for a present to give a Toronto-lover in your life this holiday season, I thought I’d very quickly mention that I’ve written a couple of books about the history of the city: The Toronto Book of the Dead and The Toronto Book of Love.
I also offer private walking tours on a variety of subjects, which I know some people have enjoyed giving as gifts this year. You can learn more about all the tours I offer here.
QUICK LINKS
The best of everything else that’s new in Toronto’s past…
NEW STATUE NEWS — The grounds of Queen’s Park are filled with statues, making it one of the central public stages for how the city tells its own history. And it has long told that story from one particular perspective. Along with honouring controversial figures like King Edward VII and Sir John A. Macdonald (who is now kept inside a protective box while the monument’s future is being reconsidered following protests targetting both of those statues during the summer of 2020), the collection isn’t exactly famous for its diversity. For decades now, only one of the historical figures depicted wasn’t a white man — and that was Queen Victoria. Now, she has company: a new statue has been added for the first time in many years… and it portrays her great-great-granddaughter, Queen Elizabeth II. Read more.
FACADE NEWS — Worrying news for what the Globe’s architecture critic Alex Bozikovic calls “one of the best 19th century buildings in Toronto.” The Stewart Building has been standing on College Street (just west of University) since the 1890s. It was designed by the city’s leading architect of the age, E.J. Lennox, who also did Old City Hall, Casa Loma, the King Edward Hotel, and the west wing of Queen’s Park. But now the Victorian building might be reduced to a facade as part of a new development.
As Bozikovic puts it, if the Stewart Building “is a teardown, then heritage policy in Toronto is hopelessly broken.”
(Click to read the full thread on Twitter.)
COAT OF ARMS NEWS — Etobicoke has decided to update its coat of arms for, uh, pretty understandable reasons. First unveiled in the 1970s, it depicts French explorer Étienne Brûlé holding a gun on one side with the word “progress”, while on the other side you’ll find an Indigenous man with a bow and the word “tradition.” Read more.
TKARONTO NEWS — Heritage Toronto has created a new digital tour that shares “sites in the city with connections to Indigenous communities and histories… From organizations like Miziwe Biik that serve as pillars of support, to the vibrant murals that colour our lanes, to the legacy of figures like Dr. Oronhyatekha.” Check it out.
THEATRE REBELS NEWS — Heritage Toronto has also unveiled another new digital tour created by Thomas Sayers, which is filled with stories about “the rebels of Toronto's theatre scene from 1950 to 1980.” Check it out.
YOU’VE GOT TO BE KIDDING ME NEWS — Oh hey, remember Rob Ford? The international embarrasment of a mayor accused of everything from smoking crack to driving drunk to sexual harassment to racist slurs to homophobic slurs to libel to death threats to domestic assault to connections with organized crime to getting high with sex workers inside the mayor’s office to using city letterhead to raise money for his high school football team to taking a TTC bus out of service so the bus could pick up his high school football team to having ties with violent extorsion and jailhouse beatings to getting so intoxicated he was thrown out of the Bier Market on St. Patrick’s Day to getting “hammered” at the Taste of the Danforth to knocking over a city councillor to ordering city staff to perform personal duties like changing lightbulbs at his home and the batteries in his kids’ toys? Well, city council is considering a plan to rename Centennial Stadium in his honour — and it has the support of Mayor Chow. Read more.
OSGOODE HALL TREES UPDATE NEWS — And while I’m grumpily remembering things… Remember how Metrolinx quickly chopped down the century-old trees on the grounds of Osgoode Hall claiming work needed to get started quickly, while critics accused them of rushing the process in order to ensure the trees were cleared before protests could gain momentum? Over at blogTO, Becky Robertson reports that ten months later the site still seems to be sitting unused. Read more.
MAGICAL PARK NEWS — On a much happier note, Guild Park is undoubtably one of the most spectacular parks in the city, perched atop the Scarborough Bluffs and filled with the ruins of some of our finest lost buildings. Jessica Fisher has written about the site’s history of art and innovation. Read more.
TORONTO HISTORY EVENTS
LOTS OF LIGHT: VICTORIAN GHOST STORIES
Thursdays & Fridays until December 15 — 7pm — Colborne Lodge
“As the year's longest nights approach, join with us to explore indoor cold weather traditions from the 1800s - decorations that remind us that summer will return, singing to warm the heart and a live candle-lit reading of a unique genre of literature - the Victorian Christmas ghost story. Explore the fears of approaching winter's darkness and the hope of the light to follow. Staff will share these stories after visitors have a short tour of the cozy Colborne Lodge.”
$20
LOTS OF LIGHT: CAROLS IN THE TAVERN AT MONTGOMGERY’S INN
Dec 16 — 7pm — Montgomery’s Inn
“Celebrate the season by singing together. Gather by the fireside in the historic tavern as our host leads traditional Christmas carols to the accompaniment of live music. Includes a light historic meal served buffet style. Drinks available for purchase at the bar.”
$45
LOTS OF LIGHT: SOLSTICE STORIES AT TODMORDEN MILLS
December 21 — 6pm — Todmorden Mills
“Join us at Todmorden Mills to celebrate the longest night of the year. Hear stories of the winter season with Elder Garry Sault, an Ojibway Elder from the Mississaugas of the Credit First Nation, share light refreshments, and craft a tabletop paper lantern to light up winter evenings.”
Free with registration!
LOTS OF LIGHT: FESTIVE CARD PRINTING AT MACKENZIE HOUSE
Until January 7 — Various Times — Mackenzie House
“Visitors are invited to choose a picture from Mackenzie House’s image collection and print a festive card on the historic printing press! (Note: the historic house is open to visitors but is currently unfurnished, as the restoration process following a 2021 flood continues.)”
Free!
I didn't know about the Theatre Rebels tour. Passing it along to the theatre community. Thanks for pulling the links together!