As Christmas approaches, fans of the New York Yankees have been left with nothing but coal in their stockings.  This isn’t by any means meant to be a slight on recently acquired catcher Russell Martin whose signing makes for a decent “stocking stuffer.”  It is the big prize though that has so far eluded the Yankees.

Fans of the Bronx Bombers expected their annual free-agent gift to be delivered in the form of Cliff Lee but were left with Ebenezer Scrooge-like feelings when he opted to return to the Philadelphia Phillies.  Now another Yankee target in Kerry Wood follows suit by making his own homecoming.

Around midnight central time, FOX Sports’ Ken Rosenthal broke the news that Wood was returning to the Chicago Cubs.  Wood, 33, has agreed to a two-year pact with the “North Siders” worth $12 million to once again become their closer.  By returning to Wrigley Field, his career has now come full circle, back to a setting in which he made his debut as a 20 year-old rookie phenom.

Winter hopes haven’t come to fruition for Yankees general manager Cashman who has been left out in the cold all offseason.  The rival Boston Red Sox have already delivered two major presents to their fans in Carl Crawford and Adrian Gonzalez, something that Yankee fans are usually accustomed to.  Acquiring Martin and oft-injured starter Mark Prior wasn’t what most imagined would be the Yanks’ biggest captures thus far.

A growing number of Yankee fans have begun to question Cashman who will need to dip into his farm system to acquire not only one but two talented starting pitchers if Andy Pettitte decides to hang up his spikes.  Speculation that the enigmatic Carlos Zambrano is on his radar isn’t encouraging and anything short of landing Felix Hernandez or Zach Greinke will only make disgruntled fans’ voices louder.

The public handling of Derek Jeter’s new deal hasn’t helped Cashman’s standing as even outside the greater New York area, fans nationwide felt he insulted the revered Yankees captain.  His comment during negotiations infuriated many non-biased hardball addicts: “We’ve encouraged him to test the market and see if there’s something he would prefer other than this. If he can, fine. That’s the way it works.”

Treating Jeter like an over-the-hill utility man in contract talks infuriated baseball fans nationwide and even the classy shortstop admitted his distaste for Cashman’s methods.

“I was pretty angry about it, but I let that be known,” Jeter said.  “I was angry about it because I was the one that said I didn’t want to do it, that I wasn’t going to (test the market).  To hear the organization tell me to go shop it when I just told you I wasn’t going to, if I’m going to be honest, I was angry about it.  I never wanted to be a free agent.”

The pressure will surely increase on Cashman if he is unable to acquire a dominant starter, make due with an unpopular trade or force unproven young arms into the Yankees rotation.  Cashman whose job is “to play Santa for the Yankees” has a long list in front of him if he is to assemble a team capable of challenging the Red Sox for the AL East, let alone a squad capable of making the World Series. 

Besides a top-tier starter or two, New York is in need of a new setup man in Wood’s absence.  David Robertson had an awful postseason, as he gave up vital runs that led to their 2010 playoff elimination at the hands of the Texas Rangers.  Joba Chamberlain can’t be trusted either as the formerly standout reliever is now seen as an unpredictable question mark.

Some baseball analysts feel that Nick Swisher should be moved after the free-spirited outfielder had yet another poor postseason.  In his two seasons as a Yankee, Swisher complied pitiful playoff averages of .128 and .176 in 2009 and 2010 respectively.  His erratic defense and lack of range also add credence to the thought that New York would be better off without the right fielder.

Instead of focusing on speedy outfielder Carl Crawford, Cashman turned his full attention to the pursuit of Lee, who behind the scenes made little indication that he wanted to come to the Bronx.  With Brett Gardner as the Yankees’ only consistent base-stealer in their lineup, Crawford would have been a welcome addition.  He would have given the Bombers two speedsters capable of swiping 50 bases apiece.

Along with Gardner and Curtis Granderson, Crawford would have made the Yankees outfield one of the most athletic in all of baseball and a long-term heir to Jeter’s spot in the top of the order.  With Crawford snapped up by the Red Sox, Cashman should still consider dealing Swisher and finding a younger, more athletic outfielder to improve New York’s flexibility in not relying on the long ball.

All of this being said, Cashman is still a very shrewd businessman.  He has stockpiled coveted minor league talents to deal away to reshape the Yankees roster into one that is worthy of returning to the Fall Classic.  It will be interesting to see how he goes about addressing his club’s needs as he definitely has his work cut out for him.

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