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Osburn attended Clearwater High School in Clearwater, Florida where he was drafted by the St. Louis Cardinals in the 33 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. In 1968, he played collegiate summer baseball with the Orleans Cardinals of the Cape Cod Baseball League. 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.