Yankees: Will Brian Cashman be the most sought after free agent

At season’s end, the Yankees could see an entire overhaul of their front office and field staff. And joining the class of this year’s free agents is a General Manager who could become the year’s most sought after signing.

The Yankees have not one, but two high ranking officials in their organization whose contracts expire at the end of this season. And both, if they decide to, could end up as prime catches in the free agent market over the winter.

Yankees manager, Joe Girardi, has received most of the attention as to what his fate will be thus far, but hiding in the shadows is a superstar with a fat resume of beneficial trades and team building acumen other teams would die for – and pay for!

Theo Epstein, the GM of the Chicago Cubs, recently set the pace for quality in this position when he signed a five-year $50 million deal. With a tweak here and a tweak there, he was able to push the right buttons leading to the Cubs first title in (we all know by now how many) years.

Today, ESPN’s Buster Olney speculates that a team like the Miami Marlins just might line up as a franchise with the money and the need to hire someone like Cashman. And in all likelihood, they would only be the beginning of the parade contending for his services. But as with anything, it’s not that simple.

The Yankees get the first dance

Cashman is under the control of the Yankees at least to the point where they, traditionally, get the first crack at him. That is, of course, if they want him back. The first thought that comes to mind is, why wouldn’t they want him back?

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Brian Cashman, if you can believe it, will be entering his third decade as the Yankees GM if he re-signs. Especially for the Yankees, that’s an eternity. And it could be that they do what organizations often do with management personnel at that juncture, adopting a stance of change for the sake of change, deciding it would be best for the team to have a new face in the position.

The question of who that might be is wide open, and we’re not going there, but it is precisely the team’s motive that brought Cashman here in the first place back in 1998 when he supplanted Bob Watson. So, it can happen.

But I wouldn’t place any bets on it happening.

Do I stay or do I go

Now, we get to the gist of the question. What is Cashman looking for? Does he want the prestige of topping Theo Epstein as the highest paid GM in the business? And, is he willing to essentially start all over again with a team like the Marlins,  who might provide the money, but are also destined to be in a rebuilding mode following the pending sale of the franchise?

And what about the unfinished business surrounding the Baby Bombers Cashman would leave behind if he went elsewhere?

Cashman is in the midst of struggling to hold the line by not selling off the future for the present. And if he succeeds and his gamble pays off with the rise of players like Gleyber Torres, Blake Rutherford, James Kaprielian, Chance Adams, et.al. wearing the pinstripes and bringing a Championship to the Bronx, how much is that worth in terms other than money?

Only Brian Cashman can answer that question.

Heady decisions both ways

These are heady decisions for both the Yankees and Cashman. The answers will come when the dust has settled on this season.

But don’t expect either party to base their choice on whether the Yankees make the playoffs this year. The stakes are higher than that, and both sides know that the next couple of seasons will determine the fate of the Yankees. Championships are now expected by ownership and the team’s fan base. And patience is already (prematurely) at a premium.

Next: Cashman struggles to keep team on course

Perhaps, a middle of the road solution can be reached. Cashman signs a three-year deal for $10 million a season ranking him about equal to Epstein, and the team moves forward with the plan underway to “youthenize” baseball, putting the Yankees on the cusp of another big-time Championship run.

Can you imagine the Yankees or Cashman having a problem with that?