Andy Pettitte went from a 22nd round draft pick to a Core Four member of the Dynasty Era Yankees.
Background
Andy Pettitte was drafted in the 22nd round of the 1990 MLB Draft under the draft-and-follow rules that allowed him to play baseball in Junior College before signing with the team in May of 1991. The lefty found success as he progressed through the Yankee minor league system, pitching to a 2.20 ERA for Low-A Greensboro in 1992 on a team that also featured Jorge Posada and Derek Jeter. He was named Minor League Pitcher of the Year by the team in 1994 after making it up to Triple-A Columbus.