So many innings have passed since Pettitte had to go through that ridiculous hazing process, owning veteran standing along with the rest of his "Core Four" teammates, five World Series titles and 15 Major League seasons after they all broke in together at the dawn of a new dynasty.
When the postseason ends, Pettitte will return to Deer Park, Texas, and ponder if he can do it again -- the same question he has mulled for three straight winters. It gets more difficult each time, but his teammates -- Derek Jeter, Jorge Posada and Mariano Rivera among them -- keep pulling him back.
"I think for me personally -- and I don't know about those guys -- last year, you started enjoying it a little bit more," said Pettitte, who will start Game 3 of the American League Championship Series on Monday. "You realize how special of an opportunity this has been. I want it as bad this year as I did last year, because I don't know if this is going to be it or not."
"It," of course, being the end of the line for Pettitte, who is 38 and missed two months of this season with a left groin injury, adding notes of frustration to a season that opened with a dazzling first half.
While Pettitte isn't ready to begin the retirement thought process, he vows that he will be "good with it whenever I make that decision, that's for sure." As in past winters, don't discount the idea that a few well-versed teammates will help woo Pettitte back, effectively telling him, "We need you -- again."
"He's been in every situation, every scenario," Jeter said. "It doesn't mean he's going to be successful, but you know he's not going to be flustered too much on the mound. I think he really uses that to his advantage. We have a lot of confidence in him, as he has confidence in himself."
Are you experienced?
They've all had the front row seats for the greatest victories, as well as a few of the toughest losses. But with the rest of the Core Four owning more yesterdays than tomorrows in The Show, the question is: How much longer can this all continue?
"You think about an organization maybe having one guy with 15 years experience," manager Joe Girardi said. "But to have basically four of them, it's really, truly amazing. They came up together and they're still together. The longevity and the success that they've been able to have together ... you think about how long each guy can continue to go."
That's a question the Yankees will have to deal with soon, with Pettitte, Jeter and Rivera all set for free agency. Posada remains under contract through 2011, and while no one actually expects Jeter and Rivera to go elsewhere, there is still the matter of paperwork to be done.
Jeter's case will be intriguing after a down season, batting .270 with 10 home runs and 67 RBIs -- a drop from the .334 average he produced in 2009.
Jeter drove the ball more late in the year and continued his late-stage defensive improvement, however, leading the Majors with a career-high .989 fielding percentage and making just six errors at age 36, suggesting he has plenty left in the tank.
"I'm going to play as long as I'm enjoying myself. I'm having a blast right now," Jeter said this year. "You work extremely hard in the offseason to make adjustments. I think I've done that, and I'm going to have to continue to make adjustments through the years."
Simply the best
The captain has taken pains to shrug off any talk of his advancing years, though if he had opened his hotel room door on the eve of the Yankees' AL Division Series in Minnesota, the front cover of USA Today would have greeted him with the headline, 'For a Yankees icon, the beginning of the end?'
"I don't read the papers and I don't listen to the newscasts," Jeter said. "I think that's the biggest thing."
Besides, the Yankees aren't ready to move on at shortstop anyway. It is generally assumed that once the issue of his next contract is tackled -- likely in reserved, quiet fashion -- Jeter will be back at his familiar position fielding ground balls next spring.
For one thing, the Yankees feel as though they can still win with Jeter up the middle. And with no immediate successor present, Alex Rodriguez installed at third base, no enticement to move Jeter to the outfield and the designated hitter spot likely needed more for Posada and A-Rod, the urgency is reduced.
"I want to play as long as I can, as long as I'm having fun, and as long as I'm being productive," Jeter said.
Posada has echoed similar thoughts. The 39-year-old finished hitting .249 with 18 homers and 57 RBIs in 120 games, seeing action in 78 starts behind the plate. Attractive for his switch-hitting power, Posada's defense has popped up as more of an issue: The banged-up backstop only caught 10 of 78 potential basestealers (11.4 percent).
"The injuries are certainly tougher to deal with as you get older," Posada said. "The funniest thing is, when you get up in the morning, you don't know how your body is going to feel. Some days are better than others. It's such a long season.
"I'm just thinking about today. I still have one more year, and when I finish that year, you can ask me that question. But I'm still having fun."
The wild card is Rivera, who probably shouldn't be anywhere near as good as he has been at age 40, converting 33 of 38 chances for New York while owning a 1.80 ERA in 61 appearances.
"It's incredible," general manager Brian Cashman said. "I know for years people have been waiting for it to stop, and thank God it hasn't. He's been the biggest reason we've been successful. Closers don't last this long. They don't do the things he does. Obviously, you're never going to see anything like this again."
Rivera said in the clubhouse-soaked aftermath of the Yankees' World Series win that he wanted to pitch five more years, and while he later backed off that statement, New York has no reason to begin searching for a successor to the closer's role Rivera has owned since 1997.
"One day that will happen, -- that day I will go," Rivera said. "And baseball will not stop because I'm not playing anymore. Baseball will continue. It happens like that in life. People come, people go."
Not yet. Now owning 41 career postseason saves after closing out two contests against the Twins, Rivera did so while generally fighting aches to his oblique and knees that knocked him out of the All-Star Game, making his dominance all the more remarkable.
"I can't even understand why you would ask. Mariano is amazing," Posada said. "Mariano is, for me, the reason why we are in this situation and the reason why we keep being in this situation. There's not another Mariano and there is never going to be another Mariano."
There can't be another Jeter, Pettitte, or Posada either, though the day will come that their jobs are passed on. A stroll through Yankee Stadium's legend-strewn Great Hall offers the reminder that, no matter how iconic the player, all great runs do come to an end.
When the Yankees decorate their building to bid farewell to each of the Core Four, adornments for Monument Park should be in order. Those legacies are already secure, but as the Yankees well know, the stories are not complete -- and their teammates still can't picture the day when it will be.
"I think Mo has a fountain of youth formula or something for all of them, so it may last forever," joked reliever Joba Chamberlain. "It's one of those things where you don't think it's ever going to end. They're always going to be the Core Four, so I think it'll last forever."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.