Stephen Drew is one of the best free agents still available with spring training just under way, and the New York Yankees are still in need of a third baseman and insurance policy for Derek Jeter at shortstop.

Presumably, this would make them a perfect match for each other. However, not all things go as expected.

Joel Sherman of the New York Post reports that the Yankees did in fact extend Drew an offer earlier this offseason—believed to be for two or three years. That deal was on the table until they rescinded following a flurry of signings. This was the Yankees’ strategy all along, writes Sherman:

Early in the offseason, the Yankees – with so many holes to fill – used a strategy of making many offers at one time, letting agents know that with each signing, they would re-assess and pull some bids. The Yankees actually made Drew an offer at that time, believed to be for two or three years, when the shortstop was still looking to do considerably better – four or five years.

And, as it happened, the Yankees spent more than they anticipated on players such as Brian McCann, Jacoby Ellsbury and Masahiro Tanaka and, at some point, rescinded the offer for Drew.

The fact that Drew was holding out for a four- or five-year deal was understandable back in the early-goings of the offseason. But he certainly shouldn’t be holding out for one now. Because, in all likelihood, he won’t be getting it.

Drew would offer the Yankees great flexibility and much needed depth. He’s a stellar fielder at shortstop, and even though he has never played at the hot corner, his skills at short certainly suggest that he could hold his own (at the very least) at a new position.

Then, after this season, Drew could slide right over to his natural position. Derek Jeter’s retirement will leave a gaping hole at the position. While Drew isn’t the long-term fix the Yankees want, he’s a nice stopgap option until they can find one.

In fact, it will make things a whole lot easier for them going into next offseason because they won’t have to worry about searching for a new shortstop. They’ll already have him on the roster.

The case for signing Drew is made even stronger when considering the fact that the Yankees are already over the $189 million payroll goal thanks to the Masahiro Tanaka signing. This is what Hal Steinbrenner told Sherman in an email: 

“No team is without concerns. We will address those concerns as we go, just as we did in several areas last year. … I am comfortable with our payroll as it stands now. Tanaka put us way over the $189 million, but I believe it will prove to be a solid investment. The rest of the pieces we will figure out as we go — just as all other teams do. We have a very good club and we will continue to improve in areas that we see need it; not just in areas that need it on paper. We need to see what actually transpires in those areas and react.”

Having confidence in your roster is a good thing, but failing to see an immediate upgrade when it’s staring you in the eyes is not. On a three-year deal, Drew would be a very, very good signing.

This isn’t the first time Drew failed to sign with the Yankees after the team showed interest in him. Prior to the 2013 season, the Yankees coveted Drew as a third baseman. He ultimately signed with the Boston Red Sox, and the Yankees ultimately ended up with Kevin Youkilis.

There’s still time for a deal to come to fruition with the Yankees, but I wouldn’t expect it to happen, even though it makes a ton of sense. There are currently four teams in on Drew, with two of those teams being known—the Red Sox and the New York Mets, tweets Jim Bowden of

One of the two other mystery teams could be the Yankees. Unfortunately, we probably won’t know until Drew puts pen to paper.


Follow me on Twitter for more about the Yankees: @kennydejohn

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