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Cat Osterman has won two Olympic medals, a gold at the 2004 Games in Athens and a silver at the 2008 Games in Beijing.
Through the 2008 Games in Beijing, that is 17 gold medals at the 2004 Summer Games in Athens.
Through the 2008 Games, the most gold medals won by a man is 14 by swimmer Michael Phelps of the United States (6 gold at the 2004 Games and 8 gold at the 2008 Games).
This being 2007, the last Winter Olympic Games was in 2006 in Turin, Italy. Germany won the most medals (29) and the most gold medals (11). In the last Summer Games in 2004, the United States won the most medals (102) and the most gold medals (36).
Three times. He swam the 200 meter butterfly in the 2000 Games in Sydney and finished 5th at the age of 15. He won 6 gold medals and 2 bronze medals at the 2004 Games in Athens and won 8 gold medals at the 2008 Games in Beijing.