Commentary

Yanks ponder new deals for aging stars

Cliff Lee -- plus older players of his own -- will be on Brian Cashman's brain this winter

Updated: October 24, 2010, 10:20 AM ET
By Andrew Marchand | ESPNNewYork.com

The most important date in the Yankees' dream offseason is the day they introduce Cliff Lee as their newest postseason cure.

But while Lee is the obvious must-have gift for the Yankees to place under their tree, he does come with a warning label in small print: Just like all of the Yankees' major decisions, there is a question about his expiration date.

It is not so much if the Yankees should go after Lee -- of course, they should -- it is how many years they should offer him. Lee, who will turn 33 next season and had back issues this year, is expected to get at least four years, probably five and the money could be north of $115 million.

The Yankees' future may very well be decided by the years they offer their key targets this offseason -- so Yankees GM Brian Cashman must negotiate with care.

The Yankees need to satisfy their players without binding the franchise to deals that may be fine in 2011, but will be gold anvils around the organization's neck by 2013.

Five days after the World Series, Derek Jeter can become a free agent for the first time in his career. While it is viewed as housekeeping that Jeter will return, the years the Yankees offer Jeter will be fascinating.

To Jeter's right is Alex Rodriguez, who is signed through 2017. How long is that? President Obama could win a second term and he still will be out of office by the time A-Rod's contract ends. How close does Jeter want to come to his frenemy's record deal?

Even though Jeter just had the worst season of his career, Cashman has to figure out what is fair based on what Jeter has done and what he could still do.

[+] EnlargeMariano Rivera
Ronald Martinez/Getty ImagesHow many years the Yanks give to players like Mariano Rivera, Derek Jeter and, yes, Cliff Lee, will have a profound impact on the team's future.

But Cashman must weigh this with the idea that if Jeter remains at short he could have two fading stars eating up between $50 million and $65 million a year on the right side of his infield.

In 2011, that may not be as big of a deal as it will be in 2012 and beyond as A-Rod and Jeter approach 40.

Mariano Rivera is already 40, but still does not appear to be slowing down. The number of years Rivera wants to pitch will be crucial as, historically, closers fade at 40. Of course, Rivera has defied history before.

Still, as it has been said for what seems like forever, there will be a time that Rivera is no longer Rivera.

While Mo hasn't fully committed to coming back, it would be shocking he didn't return, while Andy Pettitte is doing his Brett Favre-like "Should I play or shouldn't I" offseason dance.

Pettitte will probably return, but the Core Four will almost certainly be down to at least three by the end of next year. Jorge Posada, in the final season of his four-year contract, will likely not be back in 2012.

The decisions on Jeter, Rivera and maybe Pettitte, will probably be completed by the Winter Meetings, which are at Disney World in Orlando, Fla., beginning Dec. 6.

At that point, the Lee Sweepstakes will have likely heated up. If the Yankees take Lee home, Tampa will be the happiest place on earth when the Yankees begin spring training in February.

But just how long will that happiness last?

Andrew Marchand covers baseball for ESPNNewYork.com. You can follow him on Twitter.

More from ESPNNewYork.com »

Andrew Marchand is a senior writer for ESPNNewYork. He also regularly contributes to SportsCenter, Baseball Tonight, ESPNews, ESPN New York 98.7 FM and ESPN Radio. He joined ESPN in 2007 after nine years at the New York Post. Follow Andrew on Twitter »

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