"Wayne Gretzky e-mailed me and said 'congratulations on carrying the flag,'" the triathlete said Sunday. "That was so cool."
Whitfield bore the Maple Leaf into the opening ceremonies in London. The 37-year-old will race in his fourth Olympic triathlon Tuesday.
Whitfield won Olympic gold in 2000 and silver in 2008. Gretzky led the Edmonton Oilers to multiple Stanley Cups while Whitfield was in elementary school in Kingston, Ont.
When the ball and sticks came out, Whitfield and his childhood friend Ted would often pretend they were one of the Oiler superstars. Whitfield says he was often Gretzky's linemate Jari Kurri.
"You weren't allowed to be No. 99 on the street," Whitfield recalled. "We'd always brawl over who would be Wayne Gretzky. Ted's dad came out one day and said 'nobody gets to be Wayne Gretzky' just so we'd stop fighting about it."
Whitfield received Gretzky's message about a week before the Games while training in Hamilton. Whitfield was checking his e-mail and did a double-take.
"His e-mail just doesn't show up as "The Great One,'" Whitfield said. "I forwarded it to my wife and to Ted."