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.
Pettitte made his MLB debut out of the bullpen in May of 1995 after losing a competition to join the rotation that ultimately went to Sterling Hitchcock. He was sent back down to the minors shortly thereafter so that he could continue to get work at as a starter for Triple-A Columbus for a short stay before he was recalled due to injuries at the big league level. He finished third in Rookie of the Year voting and earned himself a start in the ALDS that the Yankees ultimately lost to the Mariners.
Results: 221 IP, 21-8, 3.87 ERA, 4.08 FIP, 4.6 fWAR (All-Star)
The 1996 season opened with Pettitte in the rotation after the Yankees traded away Hitchcock, and the young lefty rewarded the team's faith with his selection to the All-Star team and a 21-win season in 221 innings. His 21 wins were the most in the league that year, and he came in second in Cy Young voting. Pettitte was instrumental in the Yankees dispatching the Orioles in the ALCS by winning both his games on the team's way to a World Series matchup against the Atlanta Braves.
His first start against the Braves was a bit of a disaster after being roughed up for seven runs in just 2.1 innings. However, Pettitte got the better of Hall of Famer John Smoltz when the two faced each other in Game Five in a game that the Yankees ultimately won 1-0. His World Series victory in 1996 was the first of Pettitte's five as a member of the Yankees throughout the Dynasty Era.
What did he do after?
Pettitte hung around to win three more World Series championships with the Yankees before hitting free agency before the 2004 season. He opted to return to Texas, closer to home, and signed a contract with the Houston Astros for three years and $31.5 million. He helped lead their team to their first World Series berth in 2005. New York brought Pettitte back on a one-year deal in 2007. He returned again in 2008 and started the last game at the old Yankee Stadium as the team snapped their postseason streak. The 2009 Yankees won the World Series with Pettitte once again proving to be huge in the postseason in wins against the Angels and Phillies.
In February of 2011, Pettitte announced that he'd be retiring from baseball. He returned as a guest instructor at spring training the following season before ultimately signing a minor league deal with the team and returning to the big leagues in May of 2012. He stayed on for 2013 before announcing his retirement in September of 2014.
Pettitte finished his career as the MLB leader in postseason wins with 19. He surpassed Whitey Ford as the Yankees' all-time strikeout leader in 2013. The team announced that his number would be retired before the start of the 2015 season in a ceremony that took place this past August at the Stadium. He remains one of the most beloved Yankees of this generation, despite being the only Core Four member that did not spend his entire career in pinstripes.