Seems like I was wrong, or not up to date in being correct, about who the first Canadian to race at the Indianapolis 500 was.
A guy named "Wild Bill" Turner (I doubt his Mom named him "Wild") seems to have been the first. While originally listed as being an American it turns out he was from Toronto. And he participated in the first 500 in 1911.
More information can be found in this thread at the The Nostalgia Forum. And Tom J. has written about him in Vantage, the Vintage Racing Club of BC's newsletter, recently.
I'll just add a couple clipping found on the web. Apparently there could be some hill climb film footage out there. At least it was out there in 1914/15.
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