A brawl between clowns and firefighters at a King Street brothel. It’s just one of many bizarre stories of Toronto’s past

I actually fell into it by accident. I applied for history for university, but went into film instead. I ran an online music magazine for a while, and then started doing a strange little fiction-based history project: the Toronto Dreams Project. I was working a boring office job in Old Toronto, around the St. Lawrence Market. At lunch, I’d wander the neighbourhood and see the old buildings and read the plaques. At the same time, I was writing surreal short stories and had the idea of combining the two and making the stories dreams historical figures might have had. I printed them on little cards and started leaving them in public places for people to find, and each one would have a URL on it so you could look up the dream and find the true history. So I started writing about true history, and it took off and swallowed up the rest of my life.

How did you go from writing a “Book of the Dead” to a “Book of Love”?

They’re both such universal experiences, so there’s a nice symmetry. History so often can be taught as dry lists of dates and events and names. One thing that excites me about a lot of these stories is just what human beings historical figures really were. They are people who had these passionate, complicated lives. Parts of Toronto’s history are deeply influenced by the more personal side of their lives. By learning about them, you can learn more about the city.

What kinds of stories are you most obsessed about?

The kinds of stories where a big public figure does something very unexpected, something strange, that has these connections to the bigger forces. I was giving a talk (recently) about the Toronto Circus Riot, one of my favourite stories ever, which gets sparked by a brawl between clowns and firefighters at a brothel on King Street in the 1850s.

What’s the most shocking or mind-blowing fact you’ve ever learned about Toronto?

One of them is the power of the Orange Order — that for 120 years they just dominated the city. Today, barely anybody remembers that that happened. For most of the city’s history as a settlement, this one Northern Irish super-Protestant faction controlled the city with an iron grip.

You’ve taken advantage of social media to make history more accessible. What do you see as its greatest benefit, and what might be the downside?

People who might not realize that they’re fascinated by history until they start reading it, or don’t realize these stories are there, get to come across it accidentally.

The downside is that it’s not really in the control of the people. Just the other night, I did an anniversary thread about the Toronto streetcar tickets that were found in the ruins of the “Titanic” at the bottom of the ocean. It gets way less engagement now than it did even two years ago, because social media is sort of beholden to bigger powers. 

Toronto has a bad reputation for tearing down significant buildings. What would you say is the greatest architectural gem that we lost to development?

The one I think about the most is the old Toronto Arcade on Yonge Street, which was our first mall (demolished in 1955). The archival photos look absolutely gorgeous — this little space with two levels and wood paneling on all the storefronts. I imagine if the Toronto Arcade had just been able to survive 20 or 30 more years, people would (have begun) appreciating those old buildings, instead of just seeing them as crummy old buildings from not that long ago.

What was the impetus behind starting the Festival of Bizarre Toronto History?

I thought a festival might be a way to bring together a lot of my favourite Toronto historical storytellers in one place. I didn’t want to claim to be the Toronto History Festival. I finally had the idea that “Bizarre” would give me a niche and a quirky hook to grab people’s attention.

The festival’s going to kick off with a panel of three authors who’ve written books about strange Toronto murders. On Wednesday, we’re going to do the man who mailed himself out of slavery, Henry Box Brown, who spent the last years of his life in Toronto. I’m going to give my own lecture about Toronto’s body snatchers and grave robbers. 

Now for a lightning round, where I ask you for the most fascinating factoids about random Toronto things. Let’s start with the CN Tower.

The first thing that comes to mind is stuntman Dar Robinson, the man who jumped off the CN Tower twice (in 1979 and 1980). He’d eventually die doing a stunt not long after that (while shooting 1987’s “Million Dollar Mystery”).

Raccoons.

I’d learned a couple of years ago that raccoons nearly went extinct in Toronto, that people saw them as such pests that they were hunted and nearly driven out of existence here. There was a time when seeing a raccoon would have been very rare for someone living in Toronto a century ago, which is hard to believe. 

The Toronto Islands.

April 13 was the anniversary of the big storm that turned the islands into islands. For a lot of people, the most unexpected thing about the islands is that it was a peninsula connected to the mainland until the 1850s, when a series of storms washed away the sands and a hotel with it.

Scarborough.

Guild Park leaps to mind. People are always getting their wedding photos there, but a lot of people in Toronto have never been out there. We have this park perched on top of the bluffs, one of the most spectacular places in the whole city, filled with the ruins of these beautiful old buildings. The ones who know it love it deeply.