Andy Pettitte, left handed starting pitcher, was drafted in the 22nd round in the 1990 First Year Player Draft by the New York Yankees out of his high school in Deer Park, Texas. Andy did not sign with the Yankees that season and instead decided he would go to a junior college which, you may or may not know, allows you to get drafted every season rather then having to play two seasons of college baseball before being eligible again for the draft. Also, as the rules have since changed, no other team could talk to Andy Pettitte nor sign him until a day before the next year's draft because he did not sign with the Yankees. It did not matter anyway as Andy signed with the Yankees the very next season, in 1991, as an amateur free agent for $80,000 which was a nice bonus at that time. Andy turned down a chance to pitch for perennial powerhouse University of Texas to travel to New York.
Pettitte made his pro debut in 1991 going 4-0 with a 0.98 ERA in 6 Gulf Coast League (GCL) starts followed by a 2-2 record with a 2.18 era in the New York Penn League (NYPL). Those two levels combined Pettitte had 83 K's and 24 BB's for nearly a 4-1 ratio, which is amazing. His command was very impressive but his velocity and "stuff" were considered nothing more then average. Throughout the minors his walk rates got better and better but his K/9 rate got worse and worse. While he showed all the way through the system that he could get advanced hitters out no one was every crazy about Pettitte due to his strike outs. He never once did rank as a Top 10 prospect in any league that he played in because of the low strike out rates and Pettitte projected to be a back end of the rotation starter due to his strike out issues. Pettitte was never graded higher then a "B" graded prospect in his entire minor league career but he had an uncanny ability to hammer the strike zone, keep batters off balance with his off speed stuff, and give his team a chance to win every single time out there.
Pettitte started his Major League career in the bullpen in 1995 after losing out on the fifth starter competition to Sterling Hitchcock. Pettitte was not long for the bullpen though as he replaced an injured Jimmy Key in the rotation where he won six of his last seven starts finishing his rookie season with a 12-9 record and a 4.17 ERA. Pettitte did enough to force the Yankees to trade Hitchcock before the 1996 season and led New York to place Pettitte in the starting rotation. Pettitte started the first half of the season with a 13-4 record which earned him an All-Star appearance for the American League. Pettitte finished the 1996 season with 21 wins which led the American League and finished second in the AL Cy Young Award vote to Toronto's Pat Hentgen. Pettitte would have the last laugh though as the Yankees won the World Series in 1996.
Pettitte followed that amazing season off with 18 more victories in 1997 and a fifth place finish in the AL Cy Young Award vote. Pettitte did not get another ring in 1997 but after 16 more wins in 1998 for possibly the best team of all-time, the 1998 New York Yankees, he received his second World Series ring with a sweep of the San Diego Padres. Pettitte got rings in the 1999 World Series and 2000 World Series as well with two more great seasons from the left-handed pickoff specialist cementing his position as one of the best starting pitchers in Major League Baseball. Pettitte made his second All-Star Game trip in 2001 and even won the ALCS MVP by mowing down the Seattle Mariners although the team lost the World Series with two outs in the 9th inning against the Arizona Diamondbacks, a tough loss for all Yankees and their fans.
Pettitte continued his streak of dominance for the Yankees through the 2003 season before hitting free agency for the first time in his career. Pettitte had his contract put on the back burner by owner George Steinbrenner and GM Brian Cashman which led him into the arms of the Houston Astros before 2004 on a three-year deal worth $31.5 million. Pettitte had elbow surgery in 2004 but was back healthy in the 2005 season just in time to lead the Astros to their first World Series in their organization's history. Pettitte and Clemens, teammates now in Houston, had the two best ERA's in the National League that season but it was not enough in a World Series loss. Pettitte finished his 2006 campaign out of the playoffs before hitting free agency once again before 2007.
A wrong was righted in 2007 as the New York Yankees brought Pettitte back to the Bronx on a one year deal worth $16 million topping the Astros offer of $12 million for one season. Pettitte won his 200th game of his career in a Yankees uniform in 2007 finishing the season with a 15-9 record. Pettitte was back on a one year deal worth $16 million again in 2008 where he made the last start at the old Yankee Stadium. In that final game in Yankee Stadium Pettitte recorded his 2,000th strikeout of his career although he missed the playoffs for the first time in his Yankees tenure. Pettitte had done enough to earn a one year deal worth $5.5 million contract with incentives for the 2009 season, maybe his last.
Pettitte, along with new teammates CC Sabathia and AJ Burnett, led the team to the World Series in 2009 with Pettitte on the mound for the clinching contest in every series. Pettitte grabbed his 18th postseason win in that Game 6 of the 2009 World Series and extended his own record of series clinching wins with his seventh of his playoffs career. Pettitte decided to pitch for the Yankees for the 2010 season when he signed for one year and $11.75 million, a great decision for Pettitte and the Yankees. Pettitte started the season 11-2 with a 2.70 ERA earning another All-Star Game appearance. The 2011 season, which ended with a loss to the Detroit Tigers in the postseason, ended up being his last as he announced his retirement before the 2012 season.
Pettitte sat out the 2012 season but decided he had at least one more season in his left arm and agreed to come back on a minor league deal worth $2.5 million for the 2013 season. Pettitte missed two and a half months with a fractured left fibula that season which limited him to just a 5-4 record with a 2.87 ERA in just two starts. Pettitte still had the itch in 2013 though as he agreed to a one year deal with New York worth $12 million. During that 2013 season Pettitte earned his 250th win of his career and became the wins leader for the Yankees organization all-time passing Whitey Ford. He also passed Ford on the Yankees all-time strikeouts list as well this season with a strikeout of Twins first baseman Justin Morneau.
Pettitte announced on September 20, 2013 that he would retire at the end of the season along with Mariano Rivera and Pettitte decided to go out in a big way. Pettitte started against the Houston Astros on the day before the final game of the season and pitched a complete game victory thus closing the book on a great career with an exclamation mark. Pettitte finished with a pair of 20 game winning seasons in 1996 and 2003, he reached the World Series seven times with the Yankees and one time with the Astros winning five of them, he still holds the postseason record for victories with 19 in his career and finished with a 256-153 win-loss record. Pettitte never had a losing record in his career and holds the record for the most win-save combinations along with Jorge Posada with 81 victories.