Winter Meetings begin today in Orlando, FL. For Yankees GM Brian Cashman, it stands to be an eventful next three days as 1-of-2 things can happen: the Yankees either will or will not walk away with a contract agreement for "The Assassin" aka Cliff Lee.
Let's face it, the Yankees are in a do-or-die situation on the Lee front. If they fail to snag the southpaw, they'll be resting their hopes of a 28th Championship on a pitching rotation with a weak back-end. Without Lee, the rotation would probably look like this:
Andy Pettitte (if he returns)
The second scenario is my own "guesstimation" as I believe the Yankees could re-sign Moseley as a free agent if a deal for Lee falls through and Andy decides to retire. It's clear from both lists how having "The Assassin" in the 2-spot behind CC radically improves either lineup.
Getting Lee may not be as easy for the Yankees as many believe. According to this tweet by Jon Heyman of Sports Illustrated, Lee may be conforming to the comforts of staying with the team that he's familiar with and that is closer to his home in Arkansas.
I think that the Yankees will have to give Lee the 6th year he wants at about $23-$24 million if they want to win the Lee Sweepstakes. With both the Mariano Rivera and Derek Jeter deals done at somewhat of a bargain for the Yankees, they have enough availability to throw the kitchen sink at Lee. If the Yankees are unwilling to give that much up, it could mean that they are in serious pursuit of Carl Crawford, who is thought to walk away with the biggest overall contract of all the free agents, and are not willing to break the bank. That wouldn't make any sense to me though, as the Yankees can more than survive with their present outfieled; they have more of a dire need for Lee.
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