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Survey a group of journalists on what drew them to this wild and crazy industry and you’re bound to hear a recurring theme: Curiosity.
That’s always been a big one for me. I’ve been asking questions about anything and everything since I was first blessed with the gift of gab.
Sure, it would probably get annoying to those around me. But I truly wanted to know. To understand. To learn.
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Fortunately, that habit started to pay off when I turned 20 and landed my first newspaper job. Just like that, finding answers would be a daily requirement. Cool, eh?!
Now, exactly 30 years later, I’ve still got plenty of queries on my mind. Which takes me to my latest feature, which will appear online tomorrow morning and in Saturday’s Free Press print edition.
I’ve had a fascination with horse racing since my parents began taking me to the races when I was barely tall enough to see over the paddock where these incredible animals would be paraded around before heading out to the track.
I carried that little tradition forward when I became a father myself, taking our two kids a few times every summer. That has continued to this day, now with a group as large as 20 or so family members and friends.
A few weeks ago, I saw a social media post from Assiniboia Downs that mentioned a rookie jockey named Ciera Pruitt had just won the first race of her young career.
The name sounded familiar, and it wasn’t long before I learned she’s the 22-year-old daughter of Jerry Pruitt, who I watched race countless times at the track beginning in the early 1990s.
He was a legend, right up until his retirement in 2017 (!) at the age of 66 (!!) which made him Canada’s oldest jockey (!!!).
His wife, Lise, is no slouch, either – she’s been one of the top trainers at the Downs for years, regularly appearing in the winner’s circle.
Now it appeared their Winnipeg-born daughter was following in their footsteps – an emerging, second-generation star, it would seem.

Ciera Pruitt gallops past her parents, Jerry and Lise. (Mike Deal / Free Press)
All of this got my brain spinning. Curiosity was running high. A few phone calls and text messages later and I was off to the races – quite literally – on my next project.
Along with photographer Mike Deal, I’ve spent plenty of time with Jerry, Lise and Ciera Pruitt getting a behind-the-scenes look at their life.
That included a morning on the backstretch – a place that served as their home for many years – as they went through their various routines. An afternoon at their farm property near Rosser, where the work never really stops. And a race night at the track – inside the jockey room with Ciera, at the starting gate before a race, and with her proud parents at the finish line.
I must have asked a thousand different questions — the Pruitts can attest to how many times I began one with “This is probably a dumb question, but I’m genuinely curious” — as I learned so much about the ins and outs of what is truly an up-and-down industry.
Along the way I was treated to legendary stories of the past from Jerry – the guy is a walking, talking encyclopedia of horseracing knowledge and one heck of a character – along with insight into Lise’s role as a trainer and, of course, everything that has gone into getting Ciera ready to ride.

Jockeys, including Ciera Pruitt, and their horses walk out to the gate for the last race of the evening. (Mike Deal / Free Press)
Not only is she the youngest jockey at the Downs, she’s also the only woman – and one of only a few homegrown riders in track history.
She quickly followed up her first career win with her second, and there’s a lot more where those came from in her future.
It’s quite a story, one I’m thrilled to be able to tell. And Mike’s photos which will accompany the 4,000-word feature are truly incredible.
I hope you enjoy reading it as much as I did researching and writing it.
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