Top 10 items on Yanks' winter to-do list

Only the New York Yankees could win 95 regular-season games, sweep a division series and fall two wins shy of going to the World Series for the second straight year and yet consider their season a failure. And only the New York Yankees could spend $210 million on ballplayers -- actually $213,359,389, according to the Cot's Baseball Contracts website -- and head into the offseason with a laundry list of holes to fill, weaknesses to fix, and yet more dollars to be spent.

But that is the alternate universe the Yankees and their vociferous, ever-demanding fan base revolve in. The standards are different here, the stakes higher. In accordance with the win-or-bust mentality that was imprinted on this franchise by the late George Steinbrenner 37 years ago, as close as the Yankees came to achieving their goal this year, it only serves as a reminder of how much work they still need to do.

Herewith are 10 key issues the Yankees must resolve between now and March 31, 2011, when the chase starts all over again with Game 1 against the Detroit Tigers at Yankee Stadium:

1. Resolve the Derek Jeter contract situation

This is not as easy as it appears, because although Jeter is without question one of the 10 greatest Yankees of all time -- quite an accomplishment when you consider the names on that list -- he clearly was not the same player at 36 that he had been at 35.

The issue is not so much the money, but the years: How much longer can Jeter remain as the Yankees' starting shortstop? And how much longer can the Yankees survive with him there? He is already the oldest starting shortstop in baseball, and obviously has lost a giant step in both directions in the field and on the basepaths. Do the Yankees really want to commit for four years, at big bucks, to a player who really is not suited to play his position anymore, or to be their leadoff hitter, or to eventually move to DH?

Perhaps an eventual move to a corner outfield position, or to third base when Alex Rodriguez is ready to become a full-time DH, is the solution. But how do you get the stubborn, prideful Jeter to go along with it?

These are the issues Brian Cashman and Hal Steinbrenner have to wrestle with. It is a delicate negotiation they face, fraught with PR pitfalls and potential bruised feelings, and they no doubt will want to dispose of this powder keg as quickly and quietly as possible. Luckily for them, Jeter's agent is Casey Close, not Scott Boras. He is probably of the same mind. Twenty million a year sounds about right. But four more years? That is going to be a tough one for the Yankees to swallow.

2. Come to terms with Joe Girardi

The manager did not distinguish himself in the ALCS, but he remains the right guy for this team right now. His tendency to overmanage and rely too heavily on his numbers and charts cost him and his team against the Texas Rangers, but there's no question his is a top-notch baseball mind, and his skills at managing the men in his clubhouse might even be superior to those of his predecessor, Joe Torre. All the evidence you need is the reaction of A.J. Burnett after being told he was out of the rotation for the ALDS.

"Joe's the best manager I ever played for," Burnett said. "I know he cares about me as a person. Whatever he needs me to do, I'll do."

No doubt Girardi will be brought back, but perhaps on a provisional contract of the type Torre rejected, maybe two years with a club option for a third based on performance. But there's no way you jettison a manager who in three seasons won one World Series and missed going to second by two games.

3. Re-sign Mariano Rivera

Of all the members of the so-called Core Four, Mo will be the most difficult to replace. And judging by his 2010 season, there is no need for a replacement yet.
Still throwing bowling balls and chainsaws at 91 mph at 40, Rivera looks to have at least two good years left in him. From a PR standpoint, the Jeter negotiation may appear to be more important, but from a baseball standpoint, once again, the Yankees gotta go to Mo, and fast.

4. Whatever it takes, sign Cliff Lee

There's a reason certain sayings are used so often they become clichés -- because they're true -- and there's none truer than the one that says "You can never have too much pitching."

Despite their humongous payroll, the Yankees did not have enough. And next season, they will have even less. CC Sabathia will be around for five more seasons. That's the good news. Burnett will be around for three more. That's potentially disastrous news. Phil Hughes will get better, but unless he develops a reliable swing-and-miss out pitch, it remains to be seen whether he will ever develop into more than a back-of-the-rotation guy. And Andy Pettitte may not be back at all.

That is why it is imperative that the Yankees lock up the one pitcher they feared this postseason -- who, ironically, turned out to be a bit of a red herring. It turned out that Lee only had to beat the Yankees once to get the Rangers into the World Series, but you've got to figure that if Brian Cashman had been able to pull off that trade-deadline deal, the positions today would be reversed.

And just imagine a Yankees rotation with Sabathia and Lee as 1 and 1A. Whatever the cost, Cashman and the Steinbrenner boys have got to make that happen.

5. Straighten out A.J.

Probably the toughest job of all, but it is imperative that Girardi and Dave Eiland crack the code that unlocks the talent everyone knows is hidden in that right arm. After 13 seasons, it's possible that just can't be done, and Burnett will remain the maddeningly inconsistent and unreliable pitcher he has always been. But with a contract that makes him an untradable commodity -- three more years at $16.5 million per -- the Yankees have no choice but to give it one last, major try.

6. Find Joba a new home

The Joba Chamberlain era is clearly over in the Bronx. Once the heir apparent to Mariano, he barely got up from his perch in the bullpen in the ALDS and performed mostly mop-up duty in the ALCS.

He's fallen beneath Kerry Wood and David Robertson on the depth chart and appears to have lost the trust of his manager, his pitching coach and his GM. He's still young and talented enough to have value, however, and the Yankees should put it to use now before his stock falls any further.

7. Find a way to bring back Kerry Wood

Not at $11 million, of course, which is the cost of picking up his option for 2011. But he developed into an invaluable asset as the eighth-inning setup man for Rivera, and proved to be an accommodating presence in the clubhouse, willing to subjugate his own aspirations for the good of his new team. If he can be convinced to perform the same role again next season -- and at the same time, provide insurance at closer in the event that Mo goes down or needs a day or two -- the Yankees should make every effort to make that happen. That won't be easy, however, because you have to assume some other team will look at Wood's performance for the Yankees and want to make him their closer, an offer Wood will find very tough to resist.

8. Make a decision on Carl Crawford

To sign or not to sign? That is a huge question for the Yankees. As always, it is not a matter of money -- for all their talk about having "a budget," the Yankees have never spared a penny when they have really wanted a guy, and could easily afford both Crawford and Cliff Lee -- but of need.

The Yankees will have to decide whether, at a probable $15 million per, Crawford is really that much of an upgrade to their outfield over Curtis Granderson and Brett Gardner.

At midseason, you -- and they -- would have said of course. But Granderson had a excellent September and was one of just two Yankees to hit worth a lick in the postseason. He also plays a serviceable -- and at times very good -- center field. Gardner will never be much more than a slap hitter, but his speed creates chaos on the basepaths, and he is probably the only Yankee who can manufacture runs solely with his legs.

Is it worth it to give up on him or Granderson for a 30-year-old Crawford, who also relied heavily on his speed but is four years older than Gardner and far closer to the inevitable slowing-down process?

That's a call for Cashman and his staff to make. Perhaps the best solution is to shop Granderson with the aim of bringing Crawford in as the left fielder and returning Gardner to center.

9. Convince Jorge Posada to become a full-time DH

This is going to be about as easy as performing a root canal on a tiger. Like Jeter, Posada is a proud, stubborn man, but even he has to sense that his days as a full-time catcher are nearing an end. He can't throw out baserunners anymore, doesn't block the plate that well, and way too many pitches get past him these days. Plus, his chronic knee condition makes every-day catching a painful chore.

Yet his bat is still potent, as evidenced by Game 5 of the ALCS, and less catching could only help him at the plate. The Yankees can't afford to lose his bat. They also can't afford to allow opponents to run wild on a catcher who can't make them stay put anymore.

10. Upgrade the bench

Obviously, you can't make Posada a DH without having an adequate replacement behind the plate, and Francisco Cervelli is not it. His energy and work ethic are to be admired, but really, he doesn't hit very much and is essentially just as bad at stopping opponents from running wild as Posada is. The more you saw him play this year, the more obvious it became that he is no more than a backup. The Yankees need more than that at this vital position.

Jesus Montero and Austin Romine deserve a good long look in spring training, but at the same time Cashman should be scouring both leagues for a solid, Molina-type backstop to plug this gaping hole in the Yankees' defense.

The same goes for the infield, where Ramiro Pena is a nice little player, but not the answer to the Yankees' needs on days when Rodriguez or Jeter need a day off. And if either of them goes down for an extended length of time -- a possibility that becomes a probability as they get older -- it would likely be a season-ender. Some in the organization think Eduardo Nunez is the answer. I'm not so sure.

There are other issues, of course, such as whether Nick Swisher should be viewed as a long-term right fielder, or if he should be watched closely in 2011, his walk year, to determine if -- after two excellent regular seasons -- two straight years of postseason failure were an anomaly or a sign that he is simply not cut out for October.

Also, should they keep Marcus Thames as a righty power bat off the bench? I say yes. Farewell, reluctantly, to Lance Berkman, who added so much to their clubhouse, and not so reluctantly to Austin Kearns, who added basically nothing anywhere.

Boone Logan is worth another look, David Robertson, too, but say adios to Sergio Mitre, Chad Gaudin and Damaso Marte. Alfredo Aceves, probably headed for back surgery, may not be back either.

As for Javy Vazquez? Well, it didn't work the first time around and it didn't work the second time around.

That's one more chance than anyone usually gets with the Yankees, the only team in baseball that could come so close and still seem to be so very far away.

Wallace Matthews covers the Yankees for ESPNNewYork.com. You can follow him on Twitter.

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