Early Career
Ryan O'Keefe was educated at St Kevin's College in Melbourne, where he was the football team captain. He played for the Calder Cannons in the TAC Cup. In 1999, Ezra Bray lived with O'Keefe's family whilst on an AFL scholarship to attend Essendon Keilor College. Both Bray and O'Keefe were drafted in the 1999 AFL Draft, however Bray never played an AFL game for Geelong, who selected him with the 17th selection. O'Keefe was drafted by Sydney with the 56th selection.
In 2002, O'Keefe's younger brother Aaron died in a car accident. His family had lost another son at nine months of age to sudden infant death syndrome when Ryan was 5 years old. He also has a younger sister and brother. His father Brian played football for Fitzroy reserves and his grandfather Lionel Ryan played for Footscray in the 1950s.
O'Keefe struggled to maintain his place in the Sydney side in his first few years at the club, but his form improved when he concentrated more on running and less on weight training. He also shifted from defence to a midfield and attack role.
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