Since the Yankees offered the veteran left-hander a one-year, $10 million contract, the club has been able to secure agreements with the top three free agents on the open market, adding CC Sabathia, A.J. Burnett and now Mark Teixeira to the roster.
Despite polishing off approximately $423.5 million in future salaries -- Teixeira's deal is not yet official because the first baseman must first pass a physical -- the Yankees have not been able to come to terms with Pettitte, their first choice to complete the rotation.
Though the Yankees have not pulled their offer, they may be preparing for life without Pettitte, who has been advised not to accept such a dramatic pay cut from the $16 million he earned in each of the last two seasons.
Citing a source, Newsday reported that the Yankees felt comfortable with their offseason spending and the roster as comprised. Nothing has been finalized, but the Yankees are reportedly leaning toward not re-signing Pettitte. The New York Post characterized the chances of retaining Pettitte as "doubtful."
"Right now it's doubtful on Pettitte, given where we are financially with this stuff," a Yankees official told the Post. "But things change, especially here, if Hank and Hal [Steinbrenner] decide to do something."
Yankees general manager Brian Cashman has said repeatedly that the club wants Pettitte back for next season, having flown to Houston on Dec. 11 to apprise the left-hander of the club's situation.
Having also traveled that week to California to finalize Sabathia's deal, Cashman said that his discussion with Pettitte was less of a sales pitch and more of a face-to-face chat, with a dollar figure still needing to be reached to finalize a return.
"Andy's a free agent, and the one thing I've been consistent in saying is that we'd like to have Andy back," Cashman said last week. "I know he'd like to come back. That's set up for maybe a positive end result. It doesn't guarantee it."
Through his agents, Randy and Alan Hendricks, Pettitte confirmed after the season that he intended to pitch in 2009. Late in the year, he said that he would either pitch for the Yankees or retire, but with the club unwilling to budge he has weighed options.
Pettitte spoke in November with old friend Joe Torre to get a grasp of the situation with the Dodgers, but Torre said he expected Pettitte to go back to the Yankees.
The hurler has few suitors otherwise. The Red Sox are not thought to be a serious contender, though Pettitte might entertain pitching for the Astros or Rangers.
Pettitte told The New York Times this month that he has "made it loud and clear where I'd like to play at. I'm just basically sitting here letting my agents do their job, really."
Yankees manager Joe Girardi has spoken recently with Pettitte, and has consistently relayed that he wants him to pitch at the new Yankee Stadium in 2009. Girardi believes that Pettitte's veteran presence and history of winning in New York make him perfect to round out the staff.
"He's still excited about coming back, and they continue to talk to him," Girardi said. "Obviously it takes time. These things don't happen overnight. He was very excited about the additions and he wants to be here."
It was reported as recently as last week that Pettitte's return was "inevitable." If the Yankees are not able to bring Pettitte back, their projected rotation will feature Sabathia, Burnett, Chien-Ming Wang and Joba Chamberlain.
New York has shown interest in Ben Sheets and met with the free agent during the Winter Meetings, but the club could also cobble a fifth starter from a pack of competitors that are returning contributors from '08. That could help open a slot for pitchers like Phil Hughes, Alfredo Aceves and Dan Giese.
Pettitte, 36, was 14-14 with a 4.54 ERA in 204 innings for the Yankees in 2008. He struggled mightily in the second half, going 2-7 with a 6.23 ERA in 11 starts after July 31, but finished his year on a positive note by winning the final game played at Yankee Stadium on Sept. 21.
Yankees captain Derek Jeter said on Monday that he has spoken with Pettitte and hopes a return is in the works.
"I've been with Andy for a long time," Jeter said. "I know he really enjoys playing here in New York and it means a lot to him. I don't know all the details of it, but I would love to see him back."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.