Pettitte has won five World Series championships with the Yankees and has been an All-Star multiple times. 

Pettitte was drafted by the Yankees organization in 1990, and he signed with them a year later. After debuting in the major leagues in 1995, Pettitte finished third in voting for the American League (AL) Rookie of the Year Award. In 1996, he led the AL with 21 wins and was runner-up for the AL Cy Young Award, and two years later, he was named the Yankees' Opening Day starter. Pettitte established himself as one of the "Core Four" players who contributed to the Yankees' late-1990s dynasty that produced four championships. Pettitte won the 2001 AL Championship Series Most Valuable Player (MVP) Award in helping his team win the pennant. After spending nine seasons with the Yankees—a stint in which he won at least 12 games each season—Pettitte signed with the Houston Astros in 2004. He rejoined the Yankees in 2007. After four more seasons and an additional World Series title, he retired after the 2010 season but returned to baseball in 2012.