In November 1907, he finished just 10 yards behind close friend and sometimes-rival Tom Longboat in the gruelling 15-mile Montreal Marathon road race, with both runners being watched in the streets by a crowd of 200,000.
Upon returning to Toronto, his friends and teammates looked on in front of a crowd of 20,000 people outside Old City Hall as Jack Tait sheepishly accepted a new Grandfather Clock from the mayor for his win in the mile.
Jack Tait was also a founding member of the Balmy Beach Harriers Club in 1905, where he and other members of the West End Y and Canadian Olympic teams would set up residence - starting in the Y's 'Marathon House' on the shores of Lake Ontario - and a full training camp all summer, near the bottom of Silver Birch Ave. and the boardwalk, in Toronto's east-end Beach neighborhood.
"Smiling Jack" was well-known among fellow athletes and fans throughout North America for his raw speed and talent, public sense of fair play, and for his legendary humour.
Tait counted among his close friends and teammates the likes of Mr. Longboat, Alfred Shrubb, and Bobby Kerr, journalists Doug Laurie and Lou Marsh, and the great American middle distance stars Abel Kiviat, George Bonhag, and Mel Shepherd.
Astonishingly, after more than 60 years passed since they last saw each other, Kiviat paid tribute to his great friendship and rivalry with Tait—citing the support and encouragement he received as a naive 17-year-old from the "older runner with the big heart"—during a televised interview with Johnny Carson on The Tonight Show.
In one of his victories, Tait beat Bonhag in the Garden one night after the two were hilariously forced to share the same bed for rest in the afternoon due to overcrowding in the New York Athletic Club.
[citation needed] In 1912, facing speculative news from doctors that his heart had become enlarged from eight grueling years of training and competition, Tait finished fourth in his heat of the 1500 metres, failing to qualify for the final.
Almost fifty years later, in 1952, one of Mr. Pearson's sons, Lester Bowles Pearson—Prime Minister of Canada from 1963 to 1968—finally let it slip in great detail—in his first-ever interview about growing up in Toronto—that Jack Tait was his first and most profound boyhood hero.