From the newsletter of Onward Real Estate Group. Katherine Stevens and Robin Mcdonald
Q&A with Chris Higgins, author of The Gaol Carpenter’s Diary
What first inspired you to write The Gaol Carpenter’s Diary?
It really started while I was working on my other two books – Brick by Brick: Swansea Public School, 1890 to Present and RiverStoryz: Conversations on the Humber River. Those were both inspiring passion projects, but not really dramatic. As I dug into the research, I kept coming across these dark stories in old newspapers – murders, trials, harsh punishments – and I couldn’t believe this was all part of “Toronto the Good.”
I guess I knew it intuitively, but I’d never really pictured it until then. I got to know the jails – the Don Jail, and the one before it, the Home District Gaol – to the point where I felt like I’d actually spent some time there. So when the idea for a novel came along, it just felt natural. I already knew the world I was writing about.
Was there a specific historical event, character, or personal connection that sparked the idea?
There are eleven chapters in the book. Numerically, that bothered me – I wanted twelve or ten – but it just turned out that the eleven cases I chose covered everything I wanted to cover. They range the same way murder cases still do today: from killers who you think are “monsters” to misunderstood people who end up in terrible situations.
What I liked about these stories is that, with the exception of the Clara Ford chapter at the end, and maybe the George Bennett one, most people don’t know them – even though they’re as gripping as anything in modern true crime. If this were the U.S., the stories would already be on TV. We Canadians don’t always realize the treasure trove of material we have sitting in our archives.
The more I read these newspaper accounts, the more I came to feel for these condemned people as human beings. I struggled with the idea of ending their lives as the best we could do in terms of “justice.” And just like I’d come to know the jails so well, I started to feel like I knew the individuals too – in their most desperate moments. One line that I kept in mind is something my wife often says, is: “A person should never be judged by their worst moments.” That really became the heart of the book.
The story unfolds through the eyes of an Irish immigrant. What drew you to tell Toronto’s history from that perspective?
My narrator, Michael Callaghan, arrives from Dublin in 1849 at the age of sixteen – about the same age my grandfather was when he came to Canada in the early 1900s. In my grandfather’s case, he went off to fight in the First World War soon after. In Michael’s story, he works in a 19th-century jail and ends up building the gallows – very different experiences, but both extreme in their own ways.
When I chose Michael as my narrator, I was really trying to get into my grandfather’s head – what it’s like to leave your home so young, without family, and have to make your own way through some very harsh challenges. It’s a lonely thing – being so young and having to face up to so much on your own – and there’s a lot of loss and loneliness in that. I think that sense of dislocation comes through in the book.
Another part of my thought process was: Canada is a country of immigrants. Today those stories come from all over the world, but the Irish, English, Scots, and Welsh were immigrants too. There was a kind of diversity then that we don’t always think about now.
Another big part of the story for me was learning about the neighbourhoods in this city, many of them very much still going, while others are lost, like The Ward, and the people living there. I didn’t know much about how, as early as the 1830s, African Americans had come to Toronto and were having quite an impact on the city – building churches, businesses, and homes here. They were respected leaders, but that never made it into the textbooks when I was growing up. Writing this book helped me rediscover that missing part of our story.
Now, when I walk through Toronto – from Weston to Leslieville – I see the landscape differently. There are layers everywhere. Some of them are dark, but not all. It’s those buried things that fascinate me – what’s underneath the city we think we know.
How much of the story is rooted in historical fact versus creative imagination?
Every chapter starts from real events – real trials, real verdicts, real people. But the narrator, his thoughts and experiences, are imagined. That’s where I could explore what might have gone through someone’s mind in that time and place.
So it’s a mix. The structure and history are factual, but the emotional truth is imagined. My goal wasn’t just to be accurate – it was to bring feeling and experience into the telling. A sense of being there. To take the history out of the archives and put it into a human voice.
What part of Toronto’s early history did you most enjoy uncovering or reimagining during your research?
Definitely the geography. I loved finding out where things used to be – the old Home District Gaol near Front and Parliament, the Don River before it was straightened, the bridges, taverns, and markets. It’s amazing how much of Toronto’s past is literally under our feet.
Reimagining those spaces – hearing the echo of boots on wooden bridges or the clang of a hammer at the gaol – made it come alive for me. It changed how I see the city. Toronto isn’t static; it’s layered. Every neighbourhood has ghosts of its earlier life, and once you start noticing them, you can’t stop.