Andy Pettitte was born on June 15, 1972, in Baton Rouge, Louisiana. He is of Italian and Cajun descent, and the younger of two children born to Tommy and JoAnn Pettitte. He attended Deer Park High School in Deer Park, Texas, where he pitched for the school’s baseball team. His fastball ranged from between 85 to 87 miles per hour. He also played center and nose guard for the school’s football team.

 

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The Yankees selected Pettitte in the 22nd round of the 1990 Major League Baseball draft. Recruited by San Jacinto College North in Houston, Texas, he opted to play college baseball when coach Wayne Graham compared him to Roger Clemens. As Pettitte enrolled in a junior college rather than a four-year school, the Yankees retained the right to sign him as a draft-and-follow prospect. On May 25, 1991, he signed with the Yankees, receiving an $80,000 signing bonus ($140,669 in current dollar terms), double the Yankees’ initial offer.

In 1991, Pettitte pitched for the Gulf Coast Yankees of the Rookie-level Gulf Coast League and Oneonta Yankees of the Class A-Short Season New York–Penn League, making six starts for each team. With Oneonta, Pettitte teamed up with catcher Jorge Posada, his longtime batterymate, for the first time. Pettitte threw a knuckleball at the time. Posada struggled to catch the knuckleball, prompting Pettitte to abandon the pitch. In 1992, Pettitte pitched for the Greensboro Hornets of the Class A South Atlantic League. He pitched to a 10–4 win–loss record and a 2.20 earned run average (ERA), with 130 strikeouts and 55 walks, in 27 games started. That season, Pettitte and Posada first played with Derek Jeter. Andy Pettitte pitched for the Prince William Cannons of the Class A-Advanced Carolina League in the 1993 season, finishing the year with an 11–9 record, a 3.04 ERA, 129 strikeouts, and 47 walks in 26 starts. He also made one start for the Albany-Colonie Yankees of the Class AA Eastern League during the season. Pettitte began the 1994 season with Albany-Colonie, where he had a 7–2 record and 2.71 ERA in 11 starts, before receiving a promotion to the Columbus Clippers of the Class AAA International League. With Columbus, Pettitte had a 7–2 record and a 2.98 ERA in 16 starts. The Yankees named him their minor league pitcher of the year.

Baseball America ranked Andy the 49th best prospect in baseball prior to the 1995 season. In spring training, Pettitte competed for a spot in the starting rotation with Sterling Hitchcock. Hitchcock won the competition, and Pettitte opened the season in the bullpen, making his major league debut with the Yankees on April 29, 1995. The Yankees demoted him back to the minors on May 16 to allow him to continue starting. Eleven days later, he was recalled due to an injury to Jimmy Key. With Scott Kamieniecki and Mélido Pérez also suffering injuries, Andy became a member of the starting rotation. He recorded his first major league win on June 7. He continued to perform well through July, leading Yankees’ starters in ERA. Pettitte won six of his last seven starts, finishing the season with a 12–9 record and a 4.17 ERA, and placed third in American League (AL) Rookie of the Year Award balloting, behind Marty Cordova and Garret Anderson. He started Game Two of the 1995 American League Division Series (ALDS) against the Seattle Mariners, allowing four runs in seven innings. The Mariners won the series three games to two.

Believing Andy Pettitte was the superior pitcher, the Yankees traded Hitchcock prior to the 1996 season. Starting the season in the rotation, Pettitte had a 13–4 record at the end of the first half of the season, and made the AL All-Star team. He did not appear in the 1996 MLB All-Star Game, due to a sore arm. He led the AL with 21 wins and finished third in winning percentage (.724), and eighth in ERA (3.87). He finished second to Pat Hentgen for the AL Cy Young Award, with the smallest difference in voting since 1972. Hentgen won the award in part because he pitched more complete games than Pettitte. The Yankees defeated the Texas Rangers in the 1996 ALDS and the Baltimore Orioles in the 1996 American League Championship Series (ALCS). Pettitte won two games against the Orioles, and had his opportunity for a third start in the series cancelled by rain. Pettitte started Game One of the 1996 World Series against the Atlanta Braves. He allowed seven runs in  2 1⁄3 innings in the first game, but outdueled John Smoltz in Game Five, which the Yankees won 1–0. The Yankees defeated the Braves in Game Six to win the series, four games to two. The next year, Pettitte tied for first in games started (35), and also led the league in pickoffs (14), and double plays induced (36). He was third in the league in innings pitched (IP) ( 240 1⁄3; a career high), fourth in ERA (2.88), wins (18), and winning percentage (.720), sixth in complete games (4), eighth in strikeouts (166), and tenth in walks per nine innings (2.43). Pettitte finished fifth in the AL Cy Young Award voting. In 1998, he was seventh in the league in complete games (5; a career high), and eighth in wins (16). In the 1998 ALCS, Pettitte allowed four home runs in a game to the Cleveland Indians. The Yankees won the series, and defeated the San Diego Padres in the 1998 World Series. Pettitte started in Game Four, defeating Kevin Brown in the deciding game of the series. The Yankees won the 1999 World Series. They continued their success in the 2000 season. Pettitte finished third in the AL in wins (19), sixth in winning percentage (.679), and seventh in complete games (3). He finished off the season with his fourth World Series Title. In 2001, he made the All-Star team for the second time and was named the ALCS Most Valuable Player, after winning Games 1 and 5 against the Seattle Mariners in the 2001 ALCS. He was third in the AL in walks per nine innings (1.84), and eighth in strikeouts (164) and strikeouts per nine innings (7.36). The following year, he was ninth in the AL in winning percentage (.722) and complete games (3). Pettitte continued his success through 2003. Pettitte was second in the league in wins (21), fifth in winning percentage (.724), sixth in strikeouts (180; a career high) and strikeouts per nine innings (7.78; a career-best), eighth in games started (33), and ninth in walks per nine innings (2.16). He won the Warren Spahn Award, given annually to the best left-handed pitcher in baseball.

Pettitte became a free agent after the 2003 season. Interested in playing closer to his Deer Park home, and feeling that the Yankees were not interested in re-signing him, Pettitte signed a three-year, $31.5 million contract with the Houston Astros of the National League (NL). He switched his uniform number to #21, in honor of Roger Clemens, who previously wore that number in Boston and Toronto. His 2004 season, in which he held batters to a .226 batting average, was shortened by elbow surgery. After the 2006 season, Pettitte signed a one-year, $16 million contract with the New York Yankees with a player option for 2008 worth $16 million. The Astros had offered Pettitte $12 million for a one-year contract. Pettitte won his 200th career game on September 19, 2007. In 2007 he led the American League in starts (34), was seventh in batters faced (916), and was 9th in innings pitched ( 215 1⁄3), finishing the regular season with a 15–9 win-loss record. He also had the 5th-lowest HR/9 innings pitched ratio in the AL (0.67). After the season, Pettitte declined his 2008 option, becoming a free agent. The Yankees offered Pettitte salary arbitration, and Pettite accepted the Yankees offer. He signed a one-year, $16 million contract with the Yankees on December 12.

On September 21, 2008, Pettitte was the last starting pitcher for the Yankees at Yankee Stadium. He recorded his 2,000th career strikeout in the second inning, striking out Baltimore Orioles catcher Ramón Hernández. Pettitte led the Yankees in innings pitched in 2008 with 204. Over 14 seasons, Pettitte has averaged 158 strikeouts a season, the same number as he accumulated in 2008. Pettitte agreed to a one-year, $5.5 million contract with incentives on January 26, 2009. Based on incentives such as innings pitched and days on the active roster, Pettitte eventually earned $10.5 million for 2009. Pettitte began the 2009 season as the Yankees’ fourth starter, behind CC Sabathia, A. J. Burnett, and Chien-Ming Wang, followed by Joba Chamberlain. Pettitte was the winning pitcher as the Yankees beat the Los Angeles Angels of Anaheim in Game 6 of the ALCS on October 25, 2009, to clinch the series and advance to the World Series against the Philadelphia Phillies. This brought his career total of series-clinching wins to five, breaking the record he previously shared with Roger Clemens, Catfish Hunter and Dave Stewart. Pettitte drove in his first postseason run during Game 3 of the World Series when he got a single to center field that scored Nick Swisher. He was the winning pitcher for that game. Pettitte pitched Game 6 of the 2009 World Series on three days of rest. Experts were critical of the decision to pitch the 37-year-old on short rest, but Pettitte again was the winning pitcher in game 6 of the 2009 World Series, defeating the Philadelphia Phillies 7–3. He extended his record career total series-clinching wins to six, and extended his record for post-season career wins to 18. He became the first pitcher in Major League Baseball history to start and win three series-clinching playoff games in the same year. Derek Lowe also won three series in 2004, but with one of his wins coming in relief. Additionally, on September 27 against the Red Sox, Pettitte had been the winning pitcher in the division-clinching game. Pettitte filed for free agency after the 2009 season. He re-signed with the Yankees, receiving a one-year contract worth $11.75 million. In the first half of the 2010 season, Pettitte went 11–2 with a 2.70 ERA, earning an appearance in the 2010 Major League Baseball All-Star Game. He also won the Yankees.com mid-season Cy Young Award. Pettitte finished the season with an 11–3 record and a 3.28 ERA, his lowest since 2005.

Pettitte announced his retirement on February 4, 2011. He spent the year away from professional baseball.

Pettitte agreed to join the Yankees in spring training in 2012 as a guest instructor. Stating that his return gave him “the itch”, Pettitte signed a minor league contract with the Yankees worth $2.5 million on March 16, 2012. Pettitte began the season in the minor leagues pitching in games for different affiliates to build his endurance and pitch count. Pettitte returned on May 13, allowing 4 runs over 6 1/3 innings in a loss to the Seattle Mariners 6–2. During a game against the Cleveland Indians on June 27, 2012, Pettitte was hit hard on his ankle by a ground ball. Shortly thereafter, it was announced that Pettitte had a fractured left fibula and missed over two months. Pettitte returned on September 19, 2012 against the Blue Jays pitching five scoreless innings. He finished the season with a 5–4 record and a 2.87 ERA in 12 games started. He also made two postseason appearances. Pettitte re-signed with the Yankees for the 2013 season, agreeing to a one-year, $12 million contract. On May 17, 2013, Pettitte was put on the 15-day disabled list due to a strained left trapezius muscle. He was activated on June 3, 2013. On June 8, 2013, Pettitte recorded his 250th career win against the Seattle Mariners, becoming the 47th pitcher in Major League history to achieve as many wins. On July 1, 2013, in a game against the Minnesota Twins, Pettitte struck out Justin Morneau, thereby passing Whitey Ford as the Yankees all-time strikeout leader with 1,958. He struck out his 2,000th batter as a Yankee on September 6.

Pettitte announced on September 20 that he would retire at the end of the season. Teammate Mariano Rivera convinced him to announce it before the end of the season. Pettitte made his last regular season start at Yankee Stadium, on September 22. Andy’s last major league start, on September 28 against the Astros in Houston, tied Ford for the most games started in Yankees history (438). Pettitte pitched a complete game, receiving the victory. The Astros honored his career during the game.

On February 16, 2015, the Yankees announced that they would be retiring Pettitte’s number 46 on August 23, 2015.

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