Jockey Fleming—the jockey without a horse

June 1 | 2020

In my new book, The Smallest Objective, an entire chapter is devoted to my mother’s great-uncle Jockey Fleming, the family black sheep. During his heyday in mid-century Montreal, Jockey earned his keep as a gagman, ticket tout, and holder of bets for hockey games and the racetrack. He was celebrated by many of the most renowned sports and gossip columnists of the era. Al Palmer, in his 1950 book Montreal Confidential, wrote, “[Jockey’s] rise to fame as one of the town’s official meeters and greeters has been meteoric—whatever that means.” The image here is from a period postcard belonging to Jockey’s niece Carol, a genuine rider.