Recalled: Remembering Jan Caille and the Chicago Triathlon’s Earliest Days

The man behind the biggest triathlon in the world—and how he kept it going.

Photo: Jim Curl

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Last month, Jan Caille passed away at the age of 77. A true pioneer in the sport, Caille is perhaps best remembered for being the driving force behind the uber-popular Chicago Triathlon. Here is more about Caille’s involvement in the event—and how his tenacity led to the creation of the world’s largest race of its kind.

It all started with a broken leg.

It was 1982, and Jan Caille, then a 39-year-old former water polo player, got the idea to train for an Ironman from—what else?—an episode of Magnum PI. Except sometime before setting that audacious goal and getting to the start line, Caille sustained an injury and couldn’t train. So he did the next best thing: He organized a triathlon, instead.

Back then, the world was just waking up to the idea of swimming, then biking, then running. Enamored by the thrill of it all, Caille thought he’d spread the fun to the shores of his adopted hometown of Chicago, a city where he’d already helped put on a criterium bike race and an 8K run through his work for an advertising agency. As luck would have it, the United States Triathlon Series (USTS) had shortlisted Chicago as a destination for its burgeoning Olympic-distance elite events, and Caille was game to make it happen. It would be the first triathlon in a major urban area.

“Most were held out in the country,” Caille told the Chicago Sun-Times in 2012. “We hung our hat on [the fact] that Chicago took place in a metro area, and in one incredible and beautiful and rich city.”

Plans were ironed out for a race with a swim in Lake Michigan in the shadows of the Sears Tower and a bike and run along the city’s scenic Lake Shore Drive. Permits were obtained, and some 500 participants registered. And then, a mayoral election. In April of 1983, Harold Washington was elected as Chicago’s first African-American mayor—a celebratory moment, for sure. Only thing was Washington wasn’t keen on the idea of a triathlon taking over the city, and his office promptly scrapped the plans (and pulled the permits) for the race.

Undeterred, Caille’s team called around to find someone, anyone who could help them. Ultimately, they got the right person on the other line.

“About 10 days before the race, we connected with a woman who basically was the head of the [mayoral] office,” Caille told Chicago Athlete in 2017. “She was interested yet unknowledgeable, but she and her daughter were track athletes, and thought if running and the lakefront was involved, she’d approve it.”

On Aug. 6, 1983—the day before the race—the permits were re-issued and the very first USTS Chicago Triathlon was on. Scott Tinley (who’d already won an Ironman World Championship in 1982 and went on to win again in 1985) and Julie Ann Olson (who’d place third in Hawaii in 1984) took home the top titles, while more than 700 other pros and age-groupers streamed in afterwards. It was an auspicious start to what would eventually become the world’s largest triathlon, blossoming to include sprint, super-sprint, and kids races along with the international distance event. Within a year of the inaugural race, participation doubled; and by 2009, the event topped 9,200 participants. All with Caille at the helm, where he stayed until 2010.

Would the Chicago Triathlon have ever seen the light of day if it wasn’t for Caille? Perhaps someone else would have come along with a similar idea. But the relentless race director (who famously never carried a radio or answered his phone on race day; “if something came up, he’d find you,” his memorial reads) undoubtedly catapulted the race to a world-class event that drew the very best in the sport, along with thousands of others who showed up just to experience it all.

“Jan was a lot more than the events he created and produced, but a part of his heart and soul are still in every one of them,” reads his obituary written by Jim Curl. “He truly had a unique understanding of the business that helped the industry grow far beyond what anyone dreamed.”

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