NYY: 1995–2003, 2007–2010, 2012–2013
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. 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 American League Championship Series Most Valuable Player (MVP) Award. Pettitte's second tenure with the team lasted six seasons, interrupted by a one-year retirement in 2011, and produced a fifth World series championship.
Number retired in 2015