Pettitte, a free agent unsure whether he wants to return to the Yankees or retire, won all three clinching games for the team in the 2009 playoffs, after winning 14 others during the regular season. Along the way, he became a mentor to many of the younger pitchers in the rotation, most notably CC Sabathia and Chamberlain.
"I think he's so much bigger than on the field," Chamberlain said. "He leads by example."
As for Chamberlain, the Yankees have not yet told him whether he should prepare as a starting pitcher or a reliever. With Spring Training still three months away, Chamberlain has not even begun working out again, much less throwing.
And so his situation remains far from straightforward. A starter throughout his college and Minor League career, Chamberlain burst onto the Major League scene in 2007 as a reliever. The next season, he began the year in the bullpen before converting back into a starter around midseason. Then he began last year as a starter, but he remained tethered to a strict innings limit -- the newest incarnation of the so-called "Joba Rules."
By the time the postseason rolled around, the Yankees had decided to proceed with a three-man rotation, thereby relegating Chamberlain back to the bullpen. And his future remains unclear.
The only hints he has received have come from general manager Brian Cashman, who said last week that he envisioned both Chamberlain and Phil Hughes as starters -- but starters who are capable of relieving.
"So he didn't really answer the question," Chamberlain cracked.
No, he didn't. And he has no reason to until the Yankees have more clarity regarding the rest of their rotation.
Returning for certain are Sabathia and A.J. Burnett, the two most formidable pieces of this year's rotation. But they are the only guarantees. Should Pettitte return, he would slot in as the No. 3 starter, and Hughes -- more of a lock to start than Chamberlain -- could be No. 4.
That still leaves room for Chamberlain, if the Yankees still see him in that light. Regardless, Chamberlain said he is prepared for any role, based largely on his mixed experiences over the past three seasons.
"If it does anything, it helps me just to know that I've been put in a lot of situations and it's going to help me in the long run," Chamberlain said. "It was a great year all around, no matter what people can say about the ups and the downs. At the end of the day, we got a lot accomplished."
Now, Chamberlain is spending his offseason accomplishing more. During Tuesday's "Wrap to Rap" program, he teamed up with New Yorkers For Children to help wrap more than 1,500 holiday gifts for children in foster care in New York City. The event, presented by Delta, hit close to home for Chamberlain, whose father spent much of his childhood living in foster homes.
"Everybody does charity things, and everybody looks at it from the outside perspective of 'Why is he doing this?'" Chamberlain said. "I do it because it means something to me. I have a direct correlation to someone that was involved, and how it helped him and how he learned from it. It was something that I was excited to get involved in."
Aside from charity work, Chamberlain plans on keeping busy shuttling between New York and Nebraska, spending time with his son and his family and, of course, trying to convince Pettitte to return for one more season.
"It's always worth a shot," he said. "Andy's become one of my best friends, and we hold no punches with each other. I'll always throw a jab in there every once in a while."