But that became especially difficult on the night of Dec. 13, when Cliff Lee rocked the baseball world by taking less money to pitch for the Phillies. Suddenly, the Yankees had little choice but to count on a 38-year-old Pettitte's return.
And Pettitte, ever the pleaser, didn't want to let them down.
"I felt a tremendous amount of pressure to come back after they didn't get him," Pettitte said Friday, a morning when he announced he was retiring from baseball -- despite his ability to still pitch, and despite the pressure he felt to try to help a needy rotation in the Bronx.
"Really, that's why I started working out. I felt like I owed it to this team, to this organization. I felt like they wanted me before they got him, but I felt like they really would probably need me now that they didn't [get Lee]."
Cashman has been rather cautious in his search for starting pitching this offseason, opting against making knee-jerk signings that aren't proper fits in his mind.
Lee, though pricey, made sense in many ways for the Yankees. And without him, their rotation would be questionable, especially in the back end. That's why Pettitte -- though he said Lee's decision didn't directly alter his, one way or the other -- felt an obligation to come back and help.
But eventually, Pettitte prominently cited two reasons for hanging it up, saying, "I didn't want to come back and be bad," and latter adding, "The desire to compete is not where it was."
Finally, after several offseasons of retirement back-and-forth, Pettitte made a decision for himself.
"I think Andy is about doing things for others, and I think today is a day about doing something for himself and his family," Cashman said. "We've had a chance to share him for half a year for 16 years on the Major League side. Maybe the last few years, he's been doing more for others than himself. Today is about himself and his family and what's best for him. In terms of obligation, someone like Andy has a difficult time reconciling and sifting through being there for others. That's the way he's wired."
Just like it was during Friday's news conference, when Pettitte apologized several times for rambling and not directly answering a reporter's question, this was an offseason of waffling for the iconic left-hander.
When the Yankees were eliminated by the Rangers in the American League Championship Series, Pettitte felt he was done. And he acted on that by not rehabbing a left groin injury that put him on the shelf for two months in 2010.
"I just felt like maybe I should make sure that I'm done," he said.
So Pettitte -- late as it might have been -- went to work right around Christmas, thanks to some insistence from his wife, Laura. In early January, he strongly considered returning. Then two weeks ago, Pettitte told Laura he was ready to come back.
"I told her I was playing," he recalled saying.
But ultimately, Pettitte wasn't in the mental or emotional state he wanted. That brought him to this past weekend, when he made his decision while returning from his secluded South Texas ranch.
"He just said, 'I'm done; that's it,'" Laura said. "He had wanted to make a decision by this past week, and he did. That's one thing is when he sets his mind to something, he's pretty sure of it."
And so it ends. Pettitte retires as the all-time leader in postseason wins (19), owner of five World Series rings, 240 career victories and a 3.88 ERA.
But is this really it?
Pettitte stated "100 percent" that he will not be pitching this year. And when asked if there was a possibility of him coming back for 2012, he said, "I don't think I am," but he added, "I guess you can never say never."
"If my stomach was just churning once Opening Day started and I'm like, 'Oh my gosh, I've made a huge mistake,' and I felt like that the whole season, I can't say that I wouldn't consider maybe doing it again," he said. "But I can tell you right now I'd be embarrassed, because I've done what I've done right now."
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. This story was not subject to the approval of Major League Baseball or its clubs.