Jack McKenna was born in Sydney, Nova Scotia. He was one of Sydney’s most well-known and accomplished athletes in both track and field and bicycle racing.

McKenna’s first bicycle race was in Sydney in 1902, where he placed an astonishing second place in a three-mile race. After further training, McKenna was able to capture first place in a two-mile race at the Dominion Day races held in North Sydney in 1904. Jack finished in a time of 5 minutes, 54 ½ seconds. On the same day, he also won the half-mile bicycle race in a time of 1 minute, 15 ½ seconds.

McKenna’s training, hard work, and dedication to sports allowed him to hold the title of Maritime Track Champion from 1904-1908.