Following another brief period of contemplating retirement, the 37-year-old has decided that he wishes to pitch in 2010. Through his agent, Randy Hendricks, Pettitte has informed the Yankees that he wants to come back and that it is time to begin discussing contract terms.
Yankees general manager Brian Cashman would not address specific terms, but discussions are under way between the organization and Pettitte's representatives, and Cashman confirmed that the club has made an initial offer.
"I believe he wants to pitch," said Cashman, who has not spoken to Pettitte directly. "I've been told, in the right circumstances, he wants to pitch."
According to published reports, the Yankees' initial offer was in the $10 million range for one year -- the only length that Pettitte would be interested in.
But discussions are likely to continue from that opening point, as Pettitte accepted an incentive-laden $5.5 million deal last season and proved his value by standing tall as one of the Yankees' most reliable and durable starters of 2009.
"When you deal with money, they're never easy conversations -- especially when it's public, and you compare yourself to someone else," Cashman said. "Whether it's a one-year versus a multiyear [deal], nothing ever seems to go smooth. That's the nature of the beast when you're negotiating salary and trying to determine what's fair."
Last offseason, it took until late January for the Yankees and Pettitte to reach a one-year deal, as the lefty balked at accepting a significant pay cut from the $16 million he earned in 2008. By that time, Cashman said that New York had already spent its starting-pitching money on CC Sabathia and A.J. Burnett, which forced the club to be creative in working Pettitte into the fold.
With Hendricks finalizing the paperwork, Pettitte settled on a base salary that was bumped to approximately $11 million with performance-based incentives. After the American League Championship Series, Pettitte admitted that he thought he should have been offered a better guaranteed deal.
"Everybody knows I wasn't really happy with the contract I took," Pettitte said then. "But I wanted to take it to come back here to have a chance to do this."
Pettitte went 14-8 with a 4.16 ERA in 32 regular-season starts, then won all three clinching games in the postseason, including Game 6 of the Fall Classic against the Phillies. Cashman said that the deal offered good value for both parties.
"We made a strong, fair offer last year," Cashman said. "I think the market showed it was a good one. We stayed in on him because we believed in him, and he made a decision that was the best for him and the best for us. I'm glad he chose to stay."
Cashman said that there is no urgency at this point to hammer out a deal with Pettitte, as the Yankees had just set their annual budget on Friday during organizational meetings in Tampa, Fla.
In New York, manager Joe Girardi said on Monday that he has spoken recently with Pettitte and is encouraged by the hurler's tone.
"My feeling is that he wants to come back," Girardi said. "And obviously, he's real important to us."
In his career, the two-time All-Star is 229-135 with a 3.91 ERA, and his 192 wins as a Yankee rank him third in franchise history behind Whitey Ford and Red Ruffing. Over the past 10 years, Pettitte leads the Majors with 148 wins.
Cashman arrived at the Winter Meetings early on Monday morning and said that, with his budget in hand, his first order of business was to engage the Yankees' own free agents.
That has him filling his week by not only talking with Hendricks regarding Pettitte, but also speaking with Arn Tellem concerning Hideki Matsui and Scott Boras about Johnny Damon.
Re-signing Pettitte could mean that the Yankees would not have to engage the top free-agent starter in the market, John Lackey. With their objective to trim payroll from the $201 million figure they took to the field on Opening Day, the Bronx Bombers might try to fill out their rotation with choices further down the pecking order.
A trade for Blue Jays ace Roy Halladay remains a possibility, depending on whether the Yankees would stomach the high price in terms of talent -- potentially a mixture of Joba Chamberlain, Phil Hughes, Austin Jackson and Jesus Montero -- that it would take to woo Toronto to deal its ace within the AL East.
"It's possible something could happen," Girardi said, "but a lot of times, the Winter Meetings are just groundwork for what's going to happen in the near future."
Bryan Hoch is a reporter for MLB.com. Brittany Ghiroli contributed to this story. This story was not subject to the approval of Major League Baseball or its clubs.