Osburn began his professional career with the Triple-A Indianapolis Indians in 1971. He played for the Indians, who were in the Cincinnati Reds\' affiliated minor league organization, for the next four seasons (1971–1974). He also played for the Triple-A Sacramento Solons (1975) in the Milwaukee Brewers organization, and the Double-A Jacksonville Suns (1976) in the Kansas City Royals organization. Over his minor league career, Osburn went 43–37 with a 3.61 ERA in 134 games, 114 starts.\n', '

Osburn attended Clearwater High School in Clearwater, Florida where he was drafted by the St. Louis Cardinals in the 33rd round of the 1967 Major League Baseball draft. While attending Clearwater High School, Osburn played quarterback on the football team and was honored with the "Black and Blue Award" by The Evening Independent after he was injured in a game in September 1966. After the 1967 baseball season, the St. Petersburg Times named Osburn as the "Most Valuable Baseball Performer". Osburn played his freshman season at Rollins College. Osburn went on to attend Manatee Community College. He played for the United States national baseball team in the 1968 World Amateur Baseball Championship where he struck out 10 in seven innings pitched against the Cuba national baseball team.\n', '

At Manatee Community College in 1969, Osburn went 10–1 with a 0.74 earned run average (ERA), and 158 strikeouts. Osburn was drafted twice in 1969, first by the Chicago White Sox in the second round of the June amateur draft, and then by the Seattle Pilots in the first round of the June secondary draft. Osburn said he did not sign with the St. Louis Cardinals and the Chicago White Sox because he did not want to undersell himself, and that he was weary of signing with the Pilots because it was an organization that he "hadn\'t heard of". He ended-up not signing with the Pilots and instead went on to attend Florida State University. Osburn was selected in the first round of the 1970 Major League Baseball draft by the Cincinnati Reds, and eventually signed.\n', '

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