15 greatest upsets in Summer Olympic history

3. 2000: Gardner takes down the ‘Russian Bear’

In the history of wrestling, Aleksandr Karelin is the greatest of all-time. The “Siberian Superman,” Karelin had never lost an international match in his career going into the 2000 Sydney Olympics, and had won three straight gold medals. His opponent in the 2000 finals would be American Rulon Gardner, won had never won an international competition or NCAA championship.

It should have been an easy victory for Karelin, as the 33-year old was primed to win his fourth Olympic gold medal. However, Gardner pulled off the impossible, edging Karelin 1-0 in overtime to grab the gold. The match was forced into extra time due to a rule that states a wrestler had to win by three points in order to win in regulation.

After neither wrestler scored in the first round, Gardner scored a point on a reversal in the second, giving him the 1-0 lead. It was the first point Karelin had given up in six years, and it would be the only point Gardner would need.

The loss also ended Karelin’s career, as he retired from Olympic wrestling following the loss. To this date, his death stare during the medal ceremony is considered one of the scariest moments in Olympic history.

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