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Nineties triathletes know Simon Lessing as perhaps the greatest short-course racer ever. He was the first man to win multiple ITU world titles; he held the record for most career ITU world titles (four) until Spain’s Javier Gomez won his fifth in 2015. Lessing started 37 races over the course of his 13-year ITU career. He finished on the podium in 27 of those races, winning on 22 occasions. He only finished outside the top 10 twice.
While he represented Great Britain throughout his professional career, Lessing grew up in Durban, South Africa. Even before he grew to his eventual height of 6 foot 3 inches, he stood tall amongst his peers as a champion for the oppressed in then-apartheid South Africa. As a schoolboy, he stole duplicate books from his school’s library to give to a nearby black school that had no library at the time. As a high schooler, he withdrew from a competition to protest the exclusion of a black competitor—earning him scorn from Afrikaner-majority selection committees.
Later, flying his adopted country’s colors, he rose swiftly up the ITU ranks, and developed a fierce rivalry with up-and-coming British star Spencer Smith, who was two years younger. “It was in 1992 that we started getting triathlon magazines [in Australia] from Europe telling stories about Simon and Spencer,” says 1997 ITU world champion Chris McCormack. “They were dominating every race in Europe.”
The 1993 ITU World Championship in Manchester, England, was particularly legendary, especially for McCormack, who got to see Lessing and Smith race for the first time. Lessing was defending his first world title, and Smith would be his biggest competition after having won the junior world title the year before. There were words traded in the media leading up to the race—Smith painting himself as a true British athlete, whereas Lessing was a South African who used his U.K. passport to secure better funding and facilities. They respected each other’s racing, but their personalities clashed, and they hated losing.
“In today’s world of social media, all the vanilla posers wouldn’t tolerate it,” McCormack says. “It was real infectious, and it drew crowds and interest in triathlon like never before.”
McCormack remembers waiting in the town center with 50,000 other triathlon fans to see who would be first to transition from bike to run. There were no cell phones or social media—just the sound of the helicopter getting closer and the anticipation of a crowd ready to erupt.
“Suddenly Spencer came flying around the corner, and he was alone,” McCormack says. “The crowd was electric. Spencer leapt off his bike and threw his helmet into the adoring crowd like a gladiator.”
Smith went on to win his first world title by nearly two minutes, with Lessing running his way into second. After the race, a number of federations logged a protest that Smith should be disqualified for discarding his helmet into the crowd, but Lessing wasn’t having any of it.
“I remember his exact words,” McCormack says. “He said, ‘If you DQ Spencer, then I’ll DQ myself. Give the man his title.’ That wasn’t how Simon wanted to win. It was epic s*** that speaks highly of the man.”
By the time Lessing wrapped up his ITU career in 2003, he’d strung together a decade of dominance that has only recently been matched by Javier Gomez. Like Gomez, Lessing turned his sights on long-distance racing in his 30s, meeting lofty expectations with mixed results. He shattered the course record at his Ironman debut in Lake Placid in 2004. Many had him pegged for a win in his Kona debut that October, but lingering back problems forced him to DNF Kona in 2004 and 2005. He had one last hoorah at the inaugural Ironman 70.3 World Championships in 2006, finishing second to Craig Alexander, before retiring to focus on coaching in 2008.