Unlike the vast majority of contemporary American professional golfers O'Hair didn't go to college. He turned professional in 1999 after his junior year at high school. He entered PGA Tour Qualifying School regularly from 1999, but was unsuccessful at his first five attempts. He played on various developmental tours: the PGA Tour's official second-level developmental Nationwide Tour, the third-level Gateway Tour and the Cleveland Pro Tour. He had limited success, making the cut in only four out of eighteen starts at Nationwide Tour level.
In 2004 O'Hair made it through all three stages of PGA Tour Qualifying. His 2005 season was a dramatic success. He won the John Deere Classic and finished second at the EDS Byron Nelson Championship. His season earnings came to $2,461,482 and he won PGA Rookie of the Year honors. As of March 2006 he was the youngest man in the top fifty of the Official World Golf Rankings. After he established himself as the frontrunner for Rookie of the Year distinction with his strong finish at the EDS Byron Nelson Championship and victory at the John Deere Classic, his difficult relationship with his father became well-publicized.
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