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After missing Lee, Yankees know Montero may be key to next move

As an organization, the Yankees have become used to getting exactly what they want in the talent market by throwing around their wealth, their status and the promise of World Series rings. It was just two years ago that the Yankees completed the greatest shopping spree in sports history, picking off the top two free-agents -- CC Sabathia and Mark Teixeira -- and the fourth-best one, A.J. Burnett, for a total commitment a bit over $400 million over eight years.

Now, though, the Yankees stand, rejected, perhaps a bit embarrassed, unable to find anyone willing to take their millions. With Cliff Lee, the left-hander they'd had designs on since the summer, having agreed to a deal with the Philadelphia Phillies, the Yankees are Jon Cryer's Duckie, watching Molly Ringwald run into the arms of Andrew McCarthy and pretending that they're OK with it all.

Here's the big secret: they can be. Lee was the best pitcher on the market and would have made the Yankees better at a cost of just money. Not having him, though, leaves them pretty much where they were at the end of the 2010 season. You remember the 2010 season, right? That was when the Yankees were one of the two best teams in baseball and went to the last day of the regular season with a chance to win the AL East. Pretty much that entire team returns, now that the Yankees have re-signed Derek Jeter and Mariano Rivera. Rental Lance Berkman is gone, as is Javier Vazquez. Some contributors are free agents, such as Marcus Thames and Kerry Wood, but the core of the roster -- the starting lineup, three of the top four starters and the top three relievers -- are all under contract for 2011. Even though the Red Sox have passed the Yankees with their own acquisitions, the likelihood is that the Sox will simply switch places with the restructuring Rays, leaving the Yankees as the early favorite for the AL wild card ahead of the A's, the Angels and the Twins.

That's not to say that the Yankees still don't have work to do, beginning with making nice with Andy Pettitte. There is a steep drop-off from A.J. Burnett to the other rotation options, and few worthy candidates in the free-agent pool. (Setting aside Carl Pavano for obvious reasons, you're left with Brad Penny and assorted injury cases and fifth starters like Jeremy Bonderman, Brandon Webb and Kevin Millwood.) Pettitte seems to be in "Yankee or dad" mode, but the Yankees cannot afford to take advantage of that. They have the Lee money burning a hole in their pocket, Pettitte was a very good starter on a per-inning basis last season and has essentially had a flat decline phase. If it takes a raise from 2010's $11.8 million salary to lock Pettitte up they should pay it. The cost, in wins, for not doing so could be severe.

There's an assumption that the Yankees will use prospect Jesus Montero to acquire someone to fill the Lee-sized hole they see at the front of the rotation. They traded Montero once, remember, agreeing to a deal with Seattle for Lee himself back in July before the Mariners decided to trade him to the Rangers instead. The idea that the Yankees will use Montero, who compares to Mike Piazza both offensively and defensively, to get Zack Greinke has been in play for some time, but it's not a particularly good fit. Greinke is a very good pitcher, but he's signed through just 2012. If the Yankees are determined to trade Montero, who is one of the top five prospects in baseball, they should target less-obvious candidates who can contribute for more than 70 starts -- even if it seems like these pitchers will, or should, be untouchable.

For example, the Rays have David Price at just under two years of service time, and signed very cheaply through 2012. Given their upcoming payrolls, will they be willing to commit 15-20% of their salary dollars to Price as he approaches $10 million a year as a three-plus player in arbitration in 2013? If that sounds ridiculous, what about trading for Matt Garza, known to be available, less expensive than Price and unable to hit free agency until after 2013? The A's have a wealth of pitching and a lack of hitting; would they part with Brett Anderson -- who may be the next Pettitte -- for Montero? The Marlins have committed a lot of money to Josh Johnson through 2013, and while they have filled their catcher and DH slots, the opportunity to re-experience Miguel Cabrera -- another fair comp for Montero -- would have to be tempting. Similarly, the Giants have their future catcher in Buster Posey and re-signed first baseman Aubrey Huff, but the Yankees might consider pursuing Giants' starter Madison Bumgarner as a more productive use of Montero's value. You could also call the Dodgers, in their current state of flux and lacking anything resembling a catcher, to pry away Clayton Kershaw.

The key is to exercise patience, to see the whole board and not just limit yourself to the obvious options. Not trading Montero is just as good an idea, although given that they've already done so once and the Yankees have catching prospects behind him, it does seem inevitable that the trigger will be pulled. Just because Greinke is pricey and plays for a small-market team doesn't mean he has to be the target. The Yankees have to recognize what they have in Montero and act accordingly, aiming as high as possible to get the best return they can.

The Yankees were unable to use their money to add a frontline starter, because the situation wasn't entirely in their control. What they do with Montero is entirely in their control, however, and their disposition of this fantastic young hitter will tell us a lot about the Yankees' creativity and imagination in solving problems that writing checks can't fix.

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