Rebels, Spies & North America's First Valentine
Plus my baseball course draws near, the gruesome roots of the NHL All-Star Game, and more...
It was 1779. The American Revolution was at its bloody height and John Graves Simcoe had already seen plenty of action. This was many years before he founded the city of Toronto, when he was still a young officer in the British army, fighting against the American rebels. And there in the middle of that brutal war, he was about to fall in love.
That winter, Simcoe found himself living just outside New York City. The area was controlled by the British at the time, but there were still plenty of American rebels around. So Simcoe spent his days on patrol with his men, searching for revolutionaries, fighting bloody battles. Over the course of the war, he would gain a reputation as a hero of the British side — leading his Queen's Rangers on guerrilla-style raids, their green uniforms blending in with the forests, a white crescent moon on their hats in honour of Diana, Goddess of the Hunt. Many of the American rebels, on the other hand, would come to see him as a particularly vicious foe, blamed for massacres and remembered more than 200 years later as a psychopathic villain in an ahistorical AMC show called Turn.
But between the battles, things were much more peaceful. Simcoe was billeted with an American family who lived in Oyster Bay, a small community on Long Island. The Townsends were slave-holding tobacco farmers: they enslaved eight people at their home and even more on their plantation. Simcoe would later claim to be a passionate abolitionist, but the truth was more complicated than that — and he seems to have enjoyed his time living with the Townsends. In fact, it was there during those long winter nights on Long Island that he fell in love.
Sarah was eighteen years old, the middle of the three Townsend girls; Sally to her friends. Simcoe was 27, but still a dashing young officer looking for a wife. They say his fellow soldiers were deeply jealous of the time he got to spend with Sally. “She was the toast of these young men,” one account would later explain, “and Simcoe was regarded as a most fortunate being in basking in the daily sunshine of her charms.” The two are said to have spent plenty of days flirting that winter, and by the time February 14th came around, the young Townsend had captured Simcoe's heart.
To express the depth of his feelings, the young man turned to a relatively new English tradition. People had been sending Valentine's Day cards for centuries, but it was over the course of the 1700s that they really evolved into the popular romantic tradition we know today. And Simcoe seems to have fully embraced it — seeing it as a chance to show off his writing skills. He'd studied poetry at school and thoroughly enjoyed writing his own verse. So, to celebrate St. Valentine's Day in 1779, Simcoe penned an ode to Sally Townsend — and then gave it to her as a gift.
The poem is a fairly epic one by the standards of a Valentine — it’s thirteen stanzas long and more than 300 words — but it begins like this:
Fairest Maid where all is fair
Beauty’s pride and Nature’s care;
To you my heart I must resign
O choose me for your Valentine!
Later, it gets a bit more wordy:
Thou knows’t what powerful magick lies
Within the round of Sarah’s eyes,
Or darted thence like lightning fires,
And Heaven’s own joys around inspires;
And finally, it transforms into a prayer to the God of Love — a plea that there will be more to Simcoe's life than just endless war:
Say, shall this breast that's pained to feel
Be ever clad in horrid steel?
Nor swell to other joys than those
Of conquest o'er unworthy foes?
Shall no fair maid with equal fire
Awake the flames of soft desire[?]
[…]
"Fond Youth," the God of Love replies,
"Your answer take from Sarah's eyes."
But that wasn't all. Simcoe had more to offer than just his poetry. He also attached a sketch: two hearts, inscribed with both of their initials and joined together by Cupid's arrow.
Today, it's considered to be the very first Valentine in the history of North America.
You might be wondering how young Sally Townsend could resist such an historic overture. But the truth is that it didn't matter how much Simcoe felt for Townsend, how flattering his poetry, or romantic his art. The two could never be together. The founder of Toronto had fallen in love with the wrong woman. You see, Sally Townsend was a rebel spy.
Now that the British were in control of New York, the American general George Washington was desperate for information from inside the occupied city. So, he established a spy ring to feed him secrets from New York, as well as from Long Island and Connecticut. He called it The Culper Ring. Sally’s brother Robert was one of three men enlisted to run the scheme — and while the details are far from clear, many historians believe that he brought his sister on board as an informant.
The Culper Ring proved to be a huge success. It was in operation for five years and tipped Washington off to surprise attacks, a British counterfeiting scheme, and maybe even a plot on the general’s own life. It’s been called “the spy ring that saved America.”
But with his head firmly over his heels, Simcoe had no clue the young woman he’d fallen for was actually a secret rebel. Some historians suggest that while he was busy wooing the lovely young Townsend, she was likely spying on him the whole time.
One story in particular raises eyebrows. The British army’s Adjutant-General, John Andre, frequently met with Simcoe at the Townsend home. Andre was plotting with the rebel traitor Benedict Arnold to hand the American fort at West Point over to the British. And since it was the Culper Ring that tipped George Washington off to the plan, some believe Sally must have overheard Andre telling Simcoe about it — and then relayed that information to her brother. (Although the story wasn’t told until a century later, and it seems like the dates might not quite match up.)
In any case, looking back on Simcoe's lovelorn winter on Long Island, it seems that Sally's interest in him may have been nothing more than a rebel ruse. As the daughter of a revolutionary family, she did have plenty of reason to hate the British officer who was making himself at home in her house. It can't have helped that he chopped down her family's beloved apple orchard so he could use the wood to build defences for a nearby fort. In the end, as you might expect, Sally Townsend rejected Simcoe’s plea to take him as her Valentine. In fact, she would never marry — she died as a single woman at the age of eighty.
Simcoe wouldn't have to live with that rejection for long: his days with the Townsends were numbered. Later that same year, he was captured in an ambush and spent six months in a rebel prison. There in his dank cell, his health began to fail him. He was eventually released in a prisoner exchange so he could head home to England and recover. It was there, as he convalesced at this godfather's country home, that he met a new love interest.
His godfather's niece Elizabeth was young and smart and pretty and curious, a strong writer and a wonderful artist. The two fell in love as she nursed him back to health and as they enjoyed long walks and romantic horseback rides through the rolling green hills of Devon. By the time Simcoe was chosen to serve as the first governor of Upper Canada, they were married. They headed off to the frontier together, where they would found the town we now call Toronto.
But there is still one physical trace of Simcoe's old crush that survives to this day. You'll find it on Long Island, in the old Townsend house in Oyster Bay — their home is now open to the public as the Raynham Hall Museum. There, in the house where Simcoe once fell in love with his rebel spy, they've preserved a pane of glass from her bedroom window. There's a wistful message scratched into its surface — a few longing words of love thought to have been inscribed by the besotted British officer John Graves Simcoe: to "the adorable Miss Sally Sarah Townsend."
A shorter version of this story appears in The Toronto Book of Love — my romantic history of the city — which is available from all the usual places, including right here. If you’d like to read more about Simcoe’s complicated relationship to slavery, I wrote about that in the newsletter back in 2022. You’ll find it here.
Thank you so much to everyone who supports The Toronto History Weekly with a few dollars a month! Three more people signed up for a paid subscription last week, though a couple were forced to cancel. It’s a ton of work putting this together, so it’s only thanks to your support — and by continuing to grow that number — that I’m able to continue doing it. If you haven’t already made the switch but would like to, you can do it by clicking right here:
My Baseball Course Is Back!
There are still a few weeks left before our Toronto sports history exhibit closes at Myseum — and with the Blue Jays’ spring training also about to kick off, we’ve decided the best way to celebrate is by bringing back my online course about the history of baseball in Toronto.
We’re offering it as a Myseum Masterclass called The History of Baseball in Toronto: From Sandlot to SkyDome with Adam Bunch. It’ll begin on February 20 and run every Tuesday night at 7pm on Zoom until March 12. Registrations are $75 (plus Eventbrite fees) and will help support Myseum in all the amazing work they do.
Here’s the full course description:
Baseball was being played in Toronto more than a century before the Blue Jays were born.
In this online course, we'll explore the game's evolution in our city — from the days when it was a working class sport played by "undesirables" to Joe Carter jumping for joy in front of 50,000 screaming fans.
Along the way, we'll meet everyone from con artists and kidnappers to eccentric millionaires and feminist icons — the people who've made Toronto baseball what it is… and helped transform our city in the process.
I’ve Got Three Upcoming Talks!
I’ve got a busy couple of months coming up, including a few talks that I’m giving for local historical societies. They’re all open to the public, so I thought I’d let you know all the details in case you’d like to check any of them out…
THE TORONTO BOOK OF LOVE & THE CITY’S ROMANTIC PAST
Wednesday, February 21 — 7pm || I’ll also be talking about The Toronto Book of Love for the North York Historical Society a couple of weeks later at the North York Central Library (5120 Yonge Street). It’s free with registration. Learn more.
UNVEILING TORONTO’S ARCHITECTURAL TAPESTRY
Thursday, March 7 — 6pm || I’ll be part of this year’s annual fundraiser for the Town of York Historical Society and Toronto’s First Post Office, sharing some of my favourite stories about artists and architects from our city’s past. The event will also include presentations from artist Summer Leigh and architect Alessandro Tersigni, along with a silent auction, a pop-up stationary shop with local vendors, a pop-up art exhibition, and food and drink for sale. It’s being held in the Great Room of St. Lawrence Hall (157 King Street East), which is a spectacularly beautiful space. Learn more.
TORONTO’S FOUNDING DOG & HOW HE ALMOST GOT EATEN
Thursday, March 14 — 7:30pm || I’ll be delivering the 2024 Howland Lecture at Lambton House (4066 Old Dundas Street) for Heritage York. It will be a talk about our city’s founding canine, Jack Sharp, and how the big Newfoundland got himself into some very deep trouble. Learn more.
QUICK LINKS
The best of everything else that’s new in Toronto’s past…
“JIM CROW WITH A BEAT” NEWS — Jamie Bradburn shares the story of two Toronto teenagers who danced live on American television in 1959, sparking a racist backlash because the boy was Black and the girl was white. Read more.
CURRICULUM NEWS — The Canadian Press reports that Ontario “is introducing mandatory learning on the contributions of Black Canadians to history courses in Grades 7, 8 and 10.” Read more.
SHE SHOOTS, SHE SCORES NEWS — The Hockey Hall of Fame has a new exhibit about the history of women’s hockey, including artifacts from the brand new PWHL. Alex Arsenych writes about it for CTV. Read more.
“ICE IS HARDER THAN A HOCKEY PLAYER’S HEAD” NEWS — Jamie Bradburn also writes about the gruesome roots of the NHL’s All-Star game, which first began with a career-ending injury to Leafs winger Ace Bailey. Read more.
VICTORY NEWS — Dave LeBlanc takes a look at the interesting decisions made during the restoration of the Victory Building, given fresh life after standing on Richmond Street West since 1929. Read more.
SNIDERMAN NEWS — The iconic Sam The Record Man store on Yonge Street shut its doors nearly 20 years ago, but one of the chain’s old franchises in Belleville has actually survived all the way to 2024. Now, though, it looks like the last branch standing might be forced to close, too. Read more.
I USED TO GO TO CBC RADIO OPEN HOUSES THERE NEWS — City Council voted to give heritage designation to the building at 509 Parliament Street, which first opened at the Carlton Theatre back in 1919. I remember it best as the CBC’s Cabbagetown studio, largely because my mom used to take my sister and I to their annual open houses back when we were kids. It’s now home to a dance school. Read more.
TORONTO HISTORY EVENTS
JOSHUA GLOVER: ESCAPED SLAVE & ETOBICOKE PIONEER
February 15 — 7:30pm — Montgomery’s Inn — Etobicoke Historical Society
“Joshua Glover was born a slave in the American South. Sold in St. Louis, Missouri in 1850, he escaped and lived as a free man in Wisconsin for two years. When his former owner tried to reclaim him, a riot ensued as Abolitionists partially demolished a jail to free him. Joshua Glover then rode the Underground Railroad to a new life in Canada, establishing himself in the Township of Etobicoke. He worked for farmer Thomas Montgomery at Montgomery’s Inn and would marry twice. This is an account of slavery and the Abolitionist movement in the United States, the Underground Railroad and the life of a Black man in Etobicoke in the 1800s. Finally, we’ll look at how Joshua Glover has been remembered both in the United States and in Canada.”
Free for members; annual memberships are $25
BLACK HISTORY MONTH OPEN HOUSE
February 16 — Noon to 4:45pm — Thomas Fisher Rare Books Library
“Celebrate Black History Month at the Thomas Fisher Rare Book Library Open House! Visitors will see a display of rare books and archival materials drawn from across our collections: from books about the Underground Railroad, to the family archives of letter carrier Albert Jackson, as well as activist newspapers, literature and literary archives, cookbooks, and more.”
Free!
LORNA POPLAK ON THE DON: THE STORY OF TORONTO’S MOST INFAMOUS JAIL
February 28 — 7pm — The Beaches Sandbox — The Beach & East Toronto Historical Society
“Conceived as a ‘palace for prisoners,’ the Don Jail never lived up to its promise. Although based on progressive nineteenth-century penal reform and architectural principles, the institution quickly deteriorated into a place of infamy where both inmates and staff were in constant danger of violence and death. Its mid-twentieth-century replacement, the New Don, soon became equally tainted.”
Free!
THE CURIOUS EVOLUTION OF RIVERDALE AVENUE
February 28 — The Riverdale Historical Society
Bob Georgiou of teh Scneexplores the history of the east end street.
Contact the Riverdale Historical Society for more info
ATROCITY ON THE ATLANTIC: THE LONG WAKE OF A FORGOTTEN WAR CRIME AGAINST A CANADIAN HOSPITAL SHIP
February 29 — 8:15pm — Toronto Reference Library
“On the evening of June 27, 1918, an unarmed, clearly marked Canadian hospital ship called the Llandovery Castle was torpedoed off the coast of Ireland by a German U-boat. Sinking hospital ships violated international treaties, so the submarine commander tried to kill the survivors to conceal his war crime. ... This presentation will discuss the attack, the survivors and the deceased, why the attack was forgotten, and the long aftermath of an atrocity that continues to impact military conduct and international law today.”
Free!
PRINTING MARY ANNE SHADD’S NEWSPAPER AT MACKENZIE HOUSE
Until February 29 — Various times daily, Wed to Sun — Mackenzie House
“Join Mackenzie House for a tribute to the life and work of Mary Ann Shadd Cary, the first Black woman to publish a newspaper in North America. In 1854, she was publishing her newspaper, The Provincial Freeman, on King Street in Toronto. Visitors are invited to print a copy of Mary Ann's newspaper on the 1845 press, customized with their name!”
Free!
BLACK DEFENDERS OF UPPER CANADA TOUR AT FORT YORK
Until February 29 — Various times daily, Wed to Sun — Fort York
“Discover the contributions made by Richard Pierpoint, and the Coloured Corps, in the defence of what is now Ontario during the War of 1812. Learn about the connections between global trade, global consumption and the African Diaspora through an exploration of ingredients used in the historic kitchen.”
Free!
LORNA POPLAK ON TORONTO’S DON JAIL
March 6 — 8pm — Swansea Town Hall & Online — Swansea Historical Society
“Lorna Poplak is a Toronto-based writer, editor, and researcher. She is the author of two award-nominated non-fiction books: — The Don – The Story of Toronto’s Infamous Jail, and Drop Dead – A Horrible History of Hanging in Canada. With these and other publications, Lorna is establishing herself as an authority on the history of crime and punishment in Canada. Her presentation will include many fascinating stories about people associated with the Don Jail – the inmates, the staff, the governors, people who escaped from the Don, and people whose lives ended there at the end of a rope.”
Free, I believe!
THE LIFE & TIMES OF ALFRED LAFFERTY
March 21 — 7:30pm — Montgomery’s Inn — The Etobicoke Historical Society
“In 1869 Alfred M. Lafferty, M.A., Richmond Hill, was a witness to the marriage of William Denis Lafferty, a black farmer who lived in Etobicoke. Who was the man with the same surname and a university degree? Hilary J. Dawson’s research uncovered the story of the Lafferty family, and the successes, challenges, and tragedies they faced. The Lafferty parents arrived from the United States in the 1830s as freedom-seekers and their two older sons later farmed in Etobicoke. The youngest son, Alfred, won prizes for excellence at both Upper Canada College and the University of Toronto. Alfred M. Lafferty would be the first black High School Principal in the province. Later, he became the first Canadian-born black lawyer in Ontario.”
Free for members; annual memberships cost $25
Thank you for a wonderfully interesting piece of history, relayed in such a lovely style.
just finished reading todays news letter, wanted to say thank you for sharing insight in to history.