|City of Toronto Archives|
Douglas McCurdy hailed from Cape Breton and in 1909 was the first person in the British Empire to fly a plane (the 9th since Orville Wright to actually fly a heavier-than-air machine). In 1911, he set out to be the first to fly out of sight of land, 94 miles over open water from Key West, Florida to Havana, Cuba. The prize: $8000 (or about $100,000 today). His engine failed within sight of the Havana waterfront, but he was able to land safely (alongside some 14-foot tiger sharks) although the aircraft was a total loss. He never did get paid.