But as their American League Division Series loss sends New York toward a third consecutive premature winter, the Yankees general manager admits that the 2007-08 offseason presents "probably" one of his biggest challenges ever.
"There's no guarantees how things play out on any of this, so it'll certainly make for an interesting winter," Cashman said. "They always are, regardless."
On Tuesday, as several Yankees filtered back to the scene of the crime, taping up boxes and preparing for long drives or flights home, the most questionable faces among them kept their distance.
The final two games of the AL Division Series were possibly Joe Torre's final days of a 12-year managerial run, but 2007 may also have represented last hurrahs for a virtual cavalcade of Yankees stars including: Alex Rodriguez, Andy Pettitte, Jorge Posada, Mariano Rivera, Roger Clemens, Bobby Abreu and more.
In many cases, how the Yankees proceed with Torre could help set the dominoes for the remaining personalities. The 67-year-old manager never missed the playoffs as the Yankees' manager, but his $7 million contract for 2007 is expiring and principal owner George Steinbrenner said in a published report that Torre was not likely to return if the Yankees did not proceed to the AL Championship Series.
Through his publicist, Howard Rubenstein, Steinbrenner declined comment on Tuesday as he traveled back to his Tampa, Fla., home. Cashman would not say if he would push ownership to keep Torre, as it has been reported he did last winter.
"His reign so far here has been terrific," Cashman said. "You'd sign up for it right now if you could find that. It's been magical and it's been incredible up to '07. Now what goes on going forward will be up to discussions."
One of Torre's finest characteristics as manager was to deflect heat from his players in a sweltering media market. As he filled out perhaps his final lineup card, Torre unwittingly did that for Rodriguez.
The probable American League MVP, A-Rod holds a contract clause that permits him to opt out of the final three years of his contract until 10 days after the World Series ends, making him a free agent. Rodriguez drove in his only run of the ALDS with a seventh-inning homer in Game 4 against Rafael Perez and went 0-for-5 with four strikeouts with men on base.
But Rodriguez, always the most scrutinized of the bunch, wasn't the only Yankee who underperformed in October. Even team captain Derek Jeter, long renowned for his postseason success, was just 3-for-17 in the ALDS. On the list of reasons why the Yankees are not preparing for a Game 5 in Cleveland, A-Rod is just one.
"You're going after the wrong guy," Yankees hitting coach Kevin Long said of Rodriguez. "Alex Rodriguez works as hard as any human being and cares more about this game and what he does more than anybody I've ever been around. Those aren't the kind of guys you want to point fingers at."
With the offseason finally here, Cashman said the Yankees have yet to open discussions with Rodriguez's agent, Scott Boras, but the Yankees have long known about and recognized Rodriguez's opt-out -- inserted as a foresight when he inked a 10-year, $252 million deal with the Rangers.
Cashman has insisted that if Rodriguez opts out, as many expect him to, the Yankees will not pursue him.
|"They had the opportunities and they didn't do nothing with me. We'll see what happens. This is business. They treat it like a business, and I'm going to treat it like a business. It's nothing against the New York Yankees. It's nothing against the organization. It's just part of it."|
|-- Mariano Rivera|
"Hopefully you have a chance to retain the player prior to that date. After that date, it doesn't make as much sense, not because we can't afford it, but because it becomes a much different economic animal."
Without Rodriguez in the regular season, the Yankees probably wouldn't have even sniffed October. Early on, A-Rod was the Bombers' one-man show, batting .314 while leading the Major Leagues in runs (143), home runs (54) and RBIs (156).
Yet, the heart of the Yankees everyday lineup may have been behind the plate, as Posada assembled a renaissance season at age 36.
Though he had just two hits in 15 ALDS at-bats, Posada hit a career high .336 in the regular season, becoming the only player in big league history to bat at least .330 with 40 doubles, 20 homers and 90 RBIs in a season when he caught half of his club's games.
Posada, like Rivera, has been a lifelong Yankee. And the longtime late inning batterymates have another thing in common: they both seem to have no idea if they have played their final games in pinstripes.
"I have no idea," Posada said. "I can't comment on something that I don't know what's going to happen."
"We'll see," said Rivera, who campaigned for a contract extension in Spring Training before stifling his demands for the remainder of the year.
"They had the opportunities and they didn't do nothing with me. We'll see what happens. This is business. They treat it like a business, and I'm going to treat it like a business. It's nothing against the New York Yankees. It's nothing against the organization. It's just part of it."
The Yankees will have other decisions to make as well. Their expensive -- and, some might say, underwhelming -- investment in Clemens has concluded, with New York squeezing six regular season wins and 2 1/3 innings in Game 3 out of the 45-year-old Rocket. With ligament damage in his elbow and persistent injuries down the stretch, Clemens' next destination may well be Cooperstown.
His close friend, Pettitte, likely hasn't assembled the resume to punch his ticket to the Hall of Fame, but it may not matter. When Pettitte agreed to return to New York this season, a product of a 1996 Yankees reunion dinner with Torre, Jeter and others, he purposely insisted on having a $16 million player option written in for 2008.
If Pettitte didn't feel inclined to pitch after the 2007 season, he wouldn't feel pressured to. Though his surgically repaired left elbow held up better than expected in a 15-9 campaign, the 34-year-old Pettitte will return to Houston for the winter unsure if he has another season in him.
"I would love to be able to get this behind me and know exactly what I want to do," Pettitte said. "I wish I knew right now. There's no way or no form I would want to try to drag it out. I just have no idea."
Bryan Hoch is a reporter for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.