In fact, there should only be one question in that regard: Will anybody ever match him?
Pettitte announced his retirement during a press conference at Yankee Stadium on Friday. And with that, the 38-year-old with the Texas drawl left behind a postseason resume that is arguably the best in history -- a record 19 wins, 42 starts and 263 innings pitched en route to a 3.83 ERA and five World Series rings.
When it comes to postseason statistics, Pettitte is four ahead of John Smoltz for most wins, seven ahead of Tom Glavine for most starts, and nearly 45 ahead of Glavine with regards to innings.
When you compare his postseason track record to that of active players, it's a laugher.
Pettitte's teammate, 41-year-old closer Mariano Rivera, ranks second among active players in postseason wins with eight -- and we know he's not catching Pettitte because, well, he's a closer. After that, four are tied with seven -- Josh Beckett of the Red Sox, Cliff Lee of the Phillies, CC Sabathia of the Yankees and 35-year-old Livan Hernandez of the Nationals.
In terms of starts, only 11 other active players have at least 10 -- and Beckett and Sabathia are the closest, with 13. With regards to postseason innings pitched, Rivera ranks second among active players with 139 2/3, and behind him are Derek Lowe (95 1/3) and Beckett (93 2/3).
So, the question must be asked: How long, if ever, will it take for somebody to match Pettitte's career-postseason-win total?
To get there, one needs two things on his side: opportunities and ability.
Thanks to the talent around him, an owner who freely spent money -- and his own ability -- Pettitte was able to make 13 postseason appearances and participate in eight World Series (one of those was with the Astros in 2005) from 1995-2010.
Pettitte was asked on Friday how he was able to raise his level of play in the playoffs. The reality, he said, was simply pitching like himself.
"If you look at the numbers, my numbers are very similar in the postseason to what they would be over my career," said Pettitte. "I definitely have had a lot of good games in the postseason, and there is so much bigger of an impact on those games -- and you get so much more attention and stuff like that. But like I've said before, I feel like I just get a good peace about those games. I get a real good calmness that comes over me when I get in big games."
Now Pettitte is gone, and we are left to wonder whether his overall body of work is good enough to one day put him in the Hall of Fame. Another question we can ponder is whether or not he has retired with an unbreakable record.
Based on numbers, production and the quality of the teams they play on, Sabathia, Beckett and Lee seemingly have the best chance of reaching -- or at least approaching -- Pettitte's career-postseason-wins mark.
But Sabathia and Beckett are each 30, Lee is 32 -- and each of them are less than 40 percent of the way there. By the time Pettitte finished his age-30 season, the iconic southpaw already had 10 postseason wins. After that, he got to pitch in the playoffs in five of the following eight seasons.
So, that trio has a long climb ahead.
Perhaps somebody like Cole Hamels (six playoff wins at age 27) or Tim Lincecum (four at age 26) -- or somebody even younger with less playoff experience -- can one day break Pettitte's record for postseason victories, especially if Major League Baseball adds two additional Wild Card teams for the 2012 season, as has been proposed.
But for now, and for quite a while at least, Pettitte is king of that department. And though many will classify his regular-season numbers (240 wins, a .635 winning percentage and a 3.88 ERA) as good-but-not-great, the fact remains that Pettitte's win total on baseball's most important stage, the playoffs, is more than the total number for nine entire organizations.
"Andy took the ball every five days and competed, and competed at a very high level in a very tough division," said Joe Girardi, Pettitte's former catcher and manager.
"He's been a part of so many huge moments," Yankees general manager Brian Cashman said. "And the great thing about Andy is, he's been a part of, obviously, some special moments -- some very difficult moments. But he's been the same guy every step of the way. He has not changed one bit."
Pettitte showed early on that he had what it took to be a big-game pitcher. As a 24-year-old in Game 5 of the 1996 World Series, he notched what many still believe is his defining performance -- when he outdueled Smoltz with 8 1/3 shutout innings, en route to his first World Series title.
Over the years, he had some playoff clunkers and several more clutch performances. But overall, Pettitte believed his command of the big stage got better as time went on.
"Early in my career, I wish that I was able to handle my emotions and some of the situations in the game like I [could], I would say, over the last seven or eight years," said Pettitte, who's also tied for second with Roger Clemens in playoff strikeouts (173). "Because, literally, when I've gone into postseason games over the last seven or eight years, I [had] so much confidence and [expected] to be successful, no matter what."
Alden Gonzalez is a reporter for MLB.com. Read his blog, Gonzo and 'The Show', and follow him on Twitter @Alden_Gonzalez. This story was not subject to the approval of Major League Baseball or its clubs.