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When the Yankees selected Andy Pettitte in the 22nd round of the 1990 draft, they had no way of knowing the lanky southpaw would start nearly 400 games for them over a 16-season big league career. More than 20 years later, Pettitte intends to announce his retirement, as first reported by Michael Kay.

Although Pettitte spent three seasons with the Astros, he will be remembered as a Yankee through and through. He broke onto the scene in April of 1995, debuting in relief against the Royals with a four-run Yankee lead to protect. Pettitte would give up two runs on that day and managed only two outs, but made the first of his 479 career starts a month later. The lineup that the Yankees ran out on that faithful day included Don Mattingly at first base, Wade Boggs at third, and Randy Velarde at short (Derek Jeter would debut two days later). The next day’s starter was another rookie who you may have heard  of—Mariano Rivera.

Pettitte never won a Cy Young Award (he finished second in 1996 and had three more top-five finishes) or garnered much consideration on a Most Valuable Player ballot (he placed 14th in 1996 and 24th in 2005) but he did earn three All-Star appearances, including one in 2010. His pickoff move was so smooth—and so close to a balk—throughout his career that it finished his career as the all-time leader in that category. For what Pettitte lacked in individual accolades, he made up for in team honors. The Yankees won five World Series titles with him on the roster and made the playoffs in every season except one. As a result, Pettitte made 42 career postseason starts, 38 of which came with the Yankees, for a total of 263 innings and another 19 victories. 

There is something to be said about Pettitte’s durability too. While he always seemed on the verge of being hurt, major injuries rarely interrupted his seasons. Aside from 2004, when he underwent elbow surgery, he made only two significant visits to the DL (2002 and 2010). A groin injury was behind 2010's derailment, limiting Pettitte to 21 starts, but he still averaged 30 starts and 191 innings pitched per season for his career. His 479 starts mark the most of any pitcher over the duration of his career, while he also threw the second most innings (roughly 40 behind Greg Maddux, who made eight fewer starts). Unsurprising for someone with his longevity and Yankee pedigree, the 240 wins credited to Pettitte also mark the most, and his .635 winning percentage places him in the top 10.

The Yankees may have been clueless about Pettitte’s future when they drafted him, but their offseason maneuverings hinted at life without Andy. Steven Goldman appeared distraught while discussing the new yet rather old rotational options rounded up by Brian Cashman and this news figures to sting like–to borrow Goldman’s metaphor–a blood-filled lemon to the eye. Meanwhile, questions about Pettitte’s playing status while give way to questions about his Hall of Fame candidacy. Jay Jaffe covered the topic in October at the Pinstriped Bible and reached the conclusion that submitting an objective yes vote will prove difficult. Jay will have more on his Cooperstown credentials tomorrow.

The world has not experienced a MLB season without Pettitte for nearly two decades, but one thing is for sure: American League base runners will breathe a little easier when they step off of first.