He's back looking to add to that legacy.
In one of his most eagerly anticipated appearances in the Bronx, Pettitte makes his official return to the Yankees on Sunday when they attempt to sweep a three-game series from the Seattle Mariners.
Pettitte is 240-138 over a career spanning 16 seasons - 13 with New York and three with Houston. Along with Derek Jeter, Mariano Rivera and Jorge Posada, he was a member of all five Yankees World Series title teams since 1996. His 19 postseason wins are the most in major league history.
His 203 wins rank third in Yankees history behind Hall of Famers Whitey Ford (236) and Red Ruffing (231). Pettitte has also posted at least 10 victories in 13 different seasons in New York, matching Ford for the most in the history of the franchise.
Those achievements likely make it just a matter of time before Pettitte will join other Yankees luminaries in Monument Park - an honor which seemed to grow closer after he retired in 2010.
Any such plans were put on hold, though, after Pettitte opted to make a comeback this year. The Yankees (19-14) could use the help since Michael Pineda is out for the season with shoulder trouble and Freddy Garcia has been demoted to the bullpen due to ineffectiveness.
Pettitte, who turns 40 next month, went 0-2 with a 3.71 ERA in three minor league starts.
"I feel like I'm at a place where I can help us," he said. "I know what they expect from me. There's nothing I'm worried about. I have not had any problems."
Manager Joe Girardi has lofty expectations for Pettitte, who hasn't thrown a pitch in the majors since losing Game 3 of the AL championship series to Texas on Oct. 18, 2010. He was 11-3 with a 3.28 ERA in 21 regular-season starts that year.
"I kind of expect him to be what he was in 2010," Girardi told the team's official website. "I don't know if that is quite fair after taking a year and a half. That's what I know. That's what I'm using to seeing - him really grinding out starts, him getting double-play balls. Doing little things to help himself get out of innings.
"I worry a little about the emotions. Obviously, there's going to be a huge buzz here. When you sit out for a year and a half, you truly realize how much you miss the game."
The Yankees are 4-1 on their six-game homestand thanks largely to a resurgent rotation, which has gone 4-0 with a 1.31 ERA.
On Saturday, Phil Hughes yielded one run in 7 2-3 innings of a 6-2 win over the Mariners (15-20). Hiroki Kuroda allowed two runs over seven innings Friday's series-opening 6-2 victory.
New York hasn't swept Seattle in the Bronx since taking all three meetings May 23-25, 2008, with Pettitte getting one of those wins.
Pettitte has won four of his last five home starts against Seattle while posting a 2.29 ERA.
The Mariners, who have batted .213 and totaled 10 runs while losing of three of four, will counter Pettitte with another grizzled veteran in Kevin Millwood (0-4, 5.88 ERA), who has been moved up in the rotation due to an elbow injury to Blake Beavan.
Millwood was pulled after five innings Tuesday, surrendering five runs and eight hits with a season-high five walks in a 6-4 loss to Detroit.
The 37-year-old right-hander is 2-7 with a 5.45 ERA in 14 career starts against the Yankees, including a defeat with Atlanta during the 1999 World Series.