As I’ve written here before, particularly in some of my early posts, the Stephen Leacock Memorial Medal for Humour, one of Canada’s oldest literary prizes, played a pivotal role in my writing life. In fact, I’ve often said that it gave me my writing life when I won the 2008 Leacock Medal for my debut novel—then self-published—The Best Laid Plans. As I’ve also said before, I would have died happy having won it once. So, winning the Leacock Medal a second time in 2015 for my fourth novel, No Relation, was an extraordinary thrill.
Given my unbounded gratitude for the impact the medal had on my writing life, I have always attended the annual Leacock gala in Orillia and played whatever part in the proceedings the Leacock Associates, who administer the prize, have asked me to. And that will continue, pandemics and natural disasters aside.
So last month, it was time once again to gather in Stephen Leacock’s home town of Orillia to award the 2025 Leacock Medal for Humour. My wife, Nancy Naylor, and I drove up on the Friday afternoon and checked into our hotel to begin the Leacock gala weekend.
Friday night festivities
For the last several years, I have served as emcee for the Friday night Meet the Authors & Student Showcase event at the beautiful Hawk Ridge Golf Club just outside of Orillia. We were there that evening to introduce the three finalists for the 2025 Leacock Medal and to celebrate the winner and runners-up in the annual Leacock humorous essay contest for high school students—the winner of the Leacock Medal itself would be announced at the gala dinner the following evening. We had a full house on Friday and lots of laughs.

Leacock High School Humorous Essay Contest
The high school winner and the two runners-up read their hilarious essays and accepted their framed certificates and prize cheques. Our winner this year is Nina Yu. I would not be surprised to see any or all three of these young writers up for the Leacock Medal sometime in the future. Their stories really were very funny.
The 2025 Leacock Medal Finalists
Then it was time to introduce the three finalists for the 2025 Stephen Leacock Memorial Medal for Humour. All three, Greg Kearney, Patricia Parsons, and Natalie Sue, were in attendance. Each spoke briefly and then read a short piece from their shortlisted books. As you might expect, the readings were fun and funny, clearly reflecting the authors’ standing as Leacock Medal finalists.
“Ask the Author!”
After the readings, the three Leacock Medal finalists, as well as past winners and short and long-listed writers in attendance came to the stage for the annual “Ask the Author” Q&A session. We had no advance warning of the questions—some of which were quite off the wall—but we managed to survive and have a few laughs along the way.

The Saturday Night Gala
I arrived early for the gala dinner and finally remembered to bring and wear my Leacock Winner badge having been gently chastised in previous years for forgetting it. The room looked amazing. But I can say with first hand experience that being a finalist and having to sit through a three course dinner and all the other elements in the program until finally finding out, just as dessert is wrapping up, whether or not you’ve won the Leacock Medal, is very challenging. It makes for a very long night for the finalists.



My only formal responsibility that night was to speak for five or six minutes about one of the three books on the short list, An Evening with Birdy O’Day. Former winners, Wayne Johnston and Cathal Kelly introduced the other two books. And then it was time…
Drumroll please…
At the appointed moment, Daphne Mainprize, the President of the Leacock Associates, announced that… Natalie Sue had won the 2025 Leacock Medal for her fine novel, I Hope This Finds You Well.

The afterparty…
Many of the writers at the gala retired to the breakfast room at our hotel where plastic glasses, chips, pretzels, wine, beer, and even a bottle of Writers’ Tears Irish whiskey somehow materialized. It’s always great to talk into the night with other writers, including the newly crowned Leacock Medal winner, Albertan, Natalie Sue. (Sorry, no photos from the afterparty.)
It was another great Leacock gala weekend. Seventeen years ago, winning the Leacock Medal utterly changed my life as a writer. I hope this year’s winner, Natalie Sue, has a similar experience.
Wrapping up…
Thanks for checking out this missive. Here’s hoping you’ll subscribe—it’s free and easy—so you don’t miss any future posts. Coming up, one of my Miscellany posts covering a number of shorter items on various fronts (including revealing the full cover of my upcoming novel, The Marionette.) Stay tuned and we’ll see you in two weeks.
Thanks for the great recap. It's wonderful to celebrate the accomplishments of Canadian writers!
Thanks for highlighting Canadian authors, as they go on my "Audiobook search" list. In your recent blog on the blurbs for the upcoming novel, I found Mindful of Murder, and The Mystery of Right and Wrong. I listen to about 70 audiobooks a year, and I will say these are two of the most exceptional recordings. Both books change the 'character point-of-view' each chapter, and the audiobook "readers" give great performances, that enhance the book notably (e.g. the poetry chapters of Mystery of Right & Wrong). So thank you so much for bringing other authors to my attention.