Toronto's Most Scandalous Mayors
From brothels and syphilis to murder and mayhem...
Well, the John Tory era is over. Eight years after coming to power on a promise to end the outrageous scandals that plagued city hall, the seemingly boring choice for mayor has resigned in disgrace after his own shocking sex scandal was revealed.
But Tory is, of course, far from the only mayor in Toronto history to be caught up in a sordid scandal. Those stories have been making frontpage news literally as long as we’ve had mayors. So today, I thought I’d share the tawdry tales of eight of the most scandalous Toronto mayors ever to hold the office — a list that could easily be much longer if Substack didn’t limit the length of these posts…
THE REBEL
Toronto’s first mayor may very well have been its most scandalous — which is really saying something given some of the entries in this list. Growing up as a young man in Scotland, William Lyon Mackenzie was a drinker and a gambler; he even fathered an illegitimate child. But it was after he moved to Toronto that the trouble really started. A newspaper publisher turned politician, he was the most radical of the Reformers pushing to make Upper Canada a real democracy. And just a few years after serving as mayor, he gave up on the idea of peaceful reform and embraced violence instead.
In 1837, Mackenzie marched a rebel army down Yonge Street, hoping to overthrow the British colonial government and replace it with an independent, democratic Canadian republic. The rebellion was quickly crushed and the former mayor became the most wanted man in the colony, with a £1,000 bounty on his head. He was forced to spend the next decade living in exile before finally being pardoned and allow to return.
Today, the home his supporters bought for him is the Mackenzie House museum. Admission is free. And if you visit, you’ll still find the rebel mayor’s own copy of his wanted poster hanging on the dining room wall.
THE MURDERER
John Powell fought on the other side of Mackenzie’s rebellion, in support of the government. He was a leading judge and politician: a devout member of the Family Compact — the small group of conservative elites who ruled over our city in its early days.
The night before Mackenzie’s army marched down Yonge Street, Powell was sent out on a scouting mission, searching for rebels in the darkness outside town. I wrote about it in The Toronto Book of the Dead:
Powell and a friend ventured farther north, drawing ever closer to the rebel army. They didn’t get far before they came across four riders in the dark. At first, they thought they were fellow Tories — but, in fact, it was Mackenzie and [Captain] Anderson [another rebel leader…]
Mackenzie caught Powell and his friend by surprise and took them prisoner. He made sure the Tory judge wasn’t carrying any weapons by asking him politely if he was carrying any weapons — and then took his word as a gentleman.
Powell lied. While Mackenzie carried on, Captain Anderson took custody of the prisoners and headed back to the tavern. On the way there, Powell pulled out the pistol he was carrying, shot Anderson in the back, and made his escape. The bullet severed Anderson’s spine. He died instantly.
The Reformers would denounce Powell as a murderer for shooting Anderson in the back. But the Tories would hail him as a hero for it. Just a few weeks later, city council would unanimously pick him to be the new Mayor of Toronto.
And Powell wasn’t the only one of Mackenzie’s enemies to hold the city’s top office. Mayor William Sherwood had been part of a mob that once broke into Mackenzie’s home, trashing his newspaper office, breaking his printing press and throwing the iron type face letters into the lake. Mayor George Gurnett was accused of torture for his role in the tarring and feathering of another prominent Reformer. Early Toronto politics were often a violent affair.
THE NOTORIOUS LANDLORD
William Henry Boulton was born into one of Toronto’s most respected families. And he grew up in one of our city’s fanciest mansions: the Grange, now part of the AGO. He was counted among the members of the Family Compact and he would go on to become a leading member of the Orange Order (the fiercely Protestant society that would run Toronto for the next 100 years). By the time Boulton turned 26, his powerful connections were already winning him elections. He would go on to serve two stints as mayor.
So, it must have been quite a shock to Toronto when the news broke: Mayor Boulton was the landlord of a brothel on King Street.
As I wrote in The Toronto Book of Love, he had long known that the oyster shop was just a front. The real money was being made after hours; neighbours had been complaining about the noise. But the mayor was likely making a handsome profit off the brothel, able to charge inflated rent. So he refused to do anything about the racket, knowing he was far too well-connected to be held responsible.
Indeed, when the case of the suspicious oyster shop eventually ended up in court, Boulton wasn’t the one in trouble. Instead, it was Daniel Bloxsom — the Black man who ran the brothel — who was put on trial. Boulton’s uncle served as the judge, with the mayor sitting right next to him as his associate. Bloxsom was found guilty and fined, while Boulton faced no legal repercussions at all.
Instead, he would be judged by the voters. He lost his bid for re-election that year. But even that consequence was temporary. A decade later, William Henry Boulton would be back in the mayor’s office.
THE CORRUPT RAILWAY PROMOTER
In 1853, Toronto was rocked by one of its most infamous financial scandals. And right at the heart of the affair was Mayor John George Bowes.
Bowes had made his fortune as a merchant, but would build upon it by investing in railway companies — and then using his political power to help them. He’s the mayor who helped cut the city off from our waterfront by having railroad tracks laid along the shoreline, and who helped establish the private streetcar company that would eventually be replaced by the TTC.
But he’s mostly remembered for one massive scandal whose details are about as thrilling as you might expect the intricacies of a Victorian financial business scheme to be...
Toronto’s municipal government had invested in the construction of the city’s first railroad by issuing a bunch of stocks that promised a 6% interest rate. But it wasn’t long before Canadian interest rates rose to 7% — which meant those stock were now worth less, selling for just 75% of their original value. And that gave Mayor Bowes an idea.
He secretly convinced the Premier of Ontario that they should buy up a bunch of those stocks now that they were cheap. So they both did.
Then, Bowes got Toronto City Council to ask the provincial government to replace all the old stocks with new ones that would be worth as much as the old ones had been originally. The province agreed.
So, all the old stocks were swapped out for the new stocks. And oh would you look at that: Mayor Bowes and the Premier both just happen to own a bunch of the old stocks and now get to trade them in for the more valuable ones.
The corrupt scheme netted them a tidy profit of nearly £10,000 — which is how it became known as “The Ten Thousand Pound Job.”
When news of the scandal broke, Mayor Bowes tried to deny he’d had any direct involvement at all… before eventually admitting his role. Investigations were launched by city council and the provincial legislature. Eight city council members resigned in protest. The City sued the mayor and he was forced to pay his profit back.
But he was still a rich man. So, after being driven out of public life for a few years, he relaunched his political career, spent lavish sums on a new mayoral campaign, and returned to office once again.
THE SYPHILITIC DEVELOPER
Ernest Albert Macdonald was used to losing. He made his fortune as a developer, building entire neighbourhoods in the east end — but he lost millions when the property bubble burst at the end of the 1800s. And he was never able to replicate that early success in other fields.
He spent years championing his big dream: an aqueduct between Toronto and Georgian Bay, which could be used for transportation and hydro power. But that project never got off the ground. He launched two newspapers. Both quickly folded, and he managed to get himself kicked out of the army in the process by using one of them to argue that Canada should be annexed by the United States. When he entered politics as a way of supporting his other schemes, he ran many more losing campaigns than winning ones — including his first three attempts to become Mayor of Toronto.
It wasn’t until the year 1900 that it finally looked like Macdonald’s luck might be changing. His fourth campaign for mayor actually worked. He spent the first year of the new century leading our city, a man still in his prime who must have thought a new chapter of his life was just beginning.
But by the end of that year, it was clear Macdonald was not well. It can be decades after you get infected with syphilis before the worst of your symptoms emerge, so we’ll never know exactly how Macdonald caught his case — whether it was from sleeping with someone before he got married, or from his wife before she died, or even if had an affair. But the infamous, sexually-transmitted disease began to take its heavy toll while Macdonald still in office.
And yet, he refused to give up. Macdonald ran for re-election, but finished third. Wikipedia suggests the defeat led to a nervous breakdown, though I wonder whether it may have just been a new stage in his disease. Newspapers of the time described him as suffering from paresis — a syphilitic mental disorder known to cause hallucinations, depression, antisocial behaviour and delusions such as “ideas of great wealth, immortality, thousands of lovers, unfathomable power, apocalypsis, nihilism, self-guilt, self-blame, or bizarre hypochondriacal complaints.”
Ernest Albert Macdonald was dead within two years of that last election loss.
THE BULLY
The Toronto Sun once called Sam McBride, “the Donald Trump of Depression-era Toronto.” He was a rich man, having made a fortune in lumber, but managed to cast himself as a champion of the working class. He supported shorter workdays, votes for women, and was backed by the labour-friendly Toronto Daily Star. That reputation helped propel him into the mayor’s office for two separate stints during the late 1920s and mid-1930s. And once he got there, he wasn’t afraid to literally throw his weight around in support of a political point.
McBride was a notoriously violent presence on city council, known to grab his opponents by the throat, or pin them against a wall, or bash them with a pile of documents. He once got into a fistfight with an alderman, walking away with a black eye. Another day, he threw a can of beans at a second council member, missing his mark but leaving a dent in the chamber’s decorative woodwork.
THE RABID ORANGEMAN
Leslie Saunders was far from the only member of the Orange Order to run our city. Nearly every Mayor of Toronto between the 1830s and the 1950s was an Orangeman. Being a member of the infamously anti-Catholic organization was basically a pre-requisite for any public job in the city. Our mayors regularly appeared in the big Orange parade every year — held in an honour of a victory over Irish Catholics back in the 1600s. But few Orange mayors were as radically devoted to the cause as Leslie Saunders was.
Saunders wasn’t just the mayor, he was also Deputy Grand Master of the Orange Lodge. And he hadn’t been in office long before that association sparked a big scandal. As the date of the Orange parade approached, the mayor decided to release a statement on official city letterhead reminding Torontonians “of their British heritage” and asking them “to thank God for those whose courage against wrong hastened the dawn of freedom,” comparing that victory against Irish Catholics to victories over “the Hun, the Nazi and the Fascist.” It wasn’t exactly a reflection of our city’s growing multiculturalism in the wake of the Second World War. Outrage ensued.
Saunders refused to apologize. He was, after all, the kind of rabid Orangeman who refused to stand for “O Canada” — only for “God Save The King” — and tried to ban Catholics from being allowed to hold their own parades in our city.
But Toronto was changing. And it was with Saunders that the city’s Orange era came to an end. When he ran for re-election as “Leslie Saunders, Protestant” he was beaten by Nathan Phillips, a Jewish candidate who promised to be a mayor “for all the people.”
For the first time in its history, Toronto would be run by someone who wasn’t a Protestant. And Saunders went on to a job he might have liked more anyway: Imperial Grand President of the entire Orange Order.
THE CRACK SMOKER
Smoking crack. Driving drunk. Sexual harassment. Racist slurs. Homophobic slurs. Libel. Death threats. Domestic assault charges. Connections to organized crime. Getting high with sex workers inside the mayor’s office. Using city letterhead to raise money for his high school football team. Taking TTC buses out of service to pick up his high school football team. “I get more than enough to eat at home.” Allegations of ties to violent extorsion and jailhouse beatings, even murder. Getting thrown out of the Bier Market on St. Patrick’s Day. Getting “hammered” at the Taste of the Danforth. Knocking over a city councillor. Ordering city staff to perform personal duties, like changing lightbulbs at his home and the batteries in his kids’ toys. The list goes on and on… You obviously can’t write a post like this without including Rob Ford.
Jamie Bradburn has written a couple of great old Torontoist posts about two of these mayors, both of which were very helpful sources for this week’s newsletter. If you’d like to read more about Leslie Saunders, you’ll find it here, and a separate piece about John George Bowes and the Ten Thousand Pound Job here. The Internet Archive also has an online copy of the first volume of “Mayors of Toronto,” a book that takes you through all the politicians who ruled our city in the 1800s — it’s here.
The collages were almost all created with images from the City of Toronto Archives and the Toronto Public Library.
Just a very quick reminder that The Toronto History Weekly is a ton of work to put together, so it will only survive if enough of you are willing to switch to a paid subscription. With a few dollars a month, you’ll be helping to keep it going, supporting all the other work I do, and bringing these stories to all of those who aren’t able to contribute. You can make the switch by clicking here:
QUICK LINKS
The best of everything else that’s new in Toronto’s past…
PLAQUE SUCCESS NEWS — I won’t share much news this week since I’ve used up nearly all my length limit on those scandalous mayors, but I did quickly want to mention some good news from this week. I recently told you about the campaign looking to raise money for a plaque dedicated to Jackie Shane, the 1960s soul singer who not only one of the greatest performers our city has ever seen, but also a Black trans woman who talked pretty openly about her sexuality on stage. This week, the campaign announced on Instagram that they’ve hit their target and the plaque will be unveiled this summer! Read more.
TORONTO HISTORY EVENTS
Various times throughout February — Mackenzie House
“In 2023, we celebrate the 200th anniversary of the birth of Mary Ann Shadd Cary, the first Black woman to publish a newspaper in North America! In 1854, Mary Ann published The Provincial Freeman from King Street in Toronto. Visit the Mackenzie House printshop to print a customized copy of Mary Ann's newspaper, and a bookmark featuring one of her most famous quotes! Printing workshops are free. Pre-registration is required.”
Free with registration!
A GLIMPSE OF BLACK LIFE IN VICTORIAN TORONTO
Until February 23 — 9am to 8pm on weekdays; 9am to 5pm on weekends — Etobicoke Civic Centre Art Gallery
“Despite the prejudices imposed upon Black individuals from 1800s, their communities made significant contributions to Toronto. This exhibition recognizes how Black residents enriched our city. Presented in partnership with the City of Toronto’s Museum Services.”
Free!
TORONTO ANNUAL VINTAGE POSTCARD SHOW
February 26 — 10am to 5pm — Japanese Cultural Centre
“Canada’s largest vintage postcard sale. As many as 1 million postcards! Hundreds of topics. Find your town, country, interest (from sports, to politics, tto flowers, animals, Disney and many more).”
$7; free for members of the Toronto Postcard Club.
CITY OF TORONTO ARCHIVES: RESOURCES FOR THE GENEALOGIST
February 27 — 7:30pm — Both online & at Lansing United Church — Toronto Branch of the Ontario Genealogical Society
“Do you have family tree roots in Toronto? You can discover a lot about a person by researching where they lived. Jessica Algie, from the City of Toronto Archives, will demonstrate, step-by-step, how to find your ancestors in municipal archival records. We’ll start with online resources including maps, city directories and photos, before diving into local tax assessment rolls, which can be treasure troves of information.
“Finally, archivist John Dirks, will give you a sneak peek at an exciting, newly processed collection, Fonds 602, First Unitarian Congregation of Toronto, now available for research at the City of Toronto Archives. This collection is of particular interest to genealogists as it includes vital statistics registers of marriages, child dedications and memorial services.”
Free, I believe!
Great article. I have read both your books and reread them often. Thank you.