WWBCD?

You’ve spent the last twenty years of your life with one company, a high profile family-run business lead by a maniacal patriarch.  You started as a mere intern, working your way through the ranks to management, where you find success at a relatively young age.  

But success doesn’t last forever.  As key members of the team drift off to retirement, the struggle to replace them amidst a barren farm system leads to frustration from ownership.  Your control is diminished as your skills are questions, decisions made over your head that steer the team in the wrong direction.  Sniping and doubt swirl from members of the inner circle who may not possess the knowledge but have the owners ear.

Your job becomes more and more difficult to endure as you watch the only organization you’ve ever known drift into an abyss.  As you’re on the doorstep, ready to enter the market as an executive free agent, management comes to their senses.  What will it take?  How do we get back?  What do we need to do to right the ship?

And so, you return, fully autonomous and able to make the decisions.  Your plan goes into action immediately.  The farm system grows.  Money isn’t thrown so carelessly to the hottest name on the free agent market.  Your team continues a good level of success without reaching the Promised Land, but that’s ok.  The plan isn’t just about today but being even better tomorrow.

But then a strange thing happens.  That maniacal patriarch hits a health wall, unable to be a part of the day to day operations anymore.  His voice and support of your plan fade into past as the rest of the family take over.  They honor your agreement, to a point.  They agree with your philosophy and your plan.  They want to be fiscally responsible and build from within.  But they want the final decision.  They want to decide what is worth spending, who is worth pursuing, who is expendable.  The powers your fought so hard to attain, to put the team on the right track, seem to be vanishing.

One day, a reporter asks you if you’ll return next year.  “Because of all the work that gets involved with doing the job, it kind of prevents me from really looking ahead past this year,” you say. “I’m just doing everything I possibly can to assist the transition with the new manager, the new owners… And then the rest will take care of itself at another time.”

It’s an eerie quote, similar in tone to something you said in 2005 when it looked like the management pressure might push you out the door.  At that time, with talk of your firing swirling, you were heard to say “I’m not thinking about next year.  I’m not thinking about my situation. Just thinking about doing the job, not worrying about what comes after that. I’m paid to do a job, and I’m doing that job.”

If you’re Brian Cashman, what do you do?  Since 2006, he’s molded the New York Yankees into his ideal vehicle to move forward: a strong farm system developing young arms and high ceiling talent, combined with aggressive overseas scouting that can take advantage of the organizations financial heft, capped with an unwillingness to trade said talent or bind the team to expensive long term contracts.

He weathered the Steinbrenner storm to wrestle away the power he needed to make the Yankees not only a successful team, but a smart team that could compete through good baseball sense rather than overspending, a philosophy that has begun to permeate through Boston, Cleveland, etc.

But that philosophy may not last forever.  The Johan Santana rumblings have shown that there is a split within the organization, a willingness to sacrifice what has so carefully been pieced together in order to land the big fish and keep him out of Boston’s waters.  It’s the classic Steinbrenner panic approach, a Raul Mondesi for the next millennium, where the slightest disadvantage can be exploded into the death Nell of the team.

Cashman hasn’t subscribed to that point of view since being given the reigns and one has to wonder how easily he wants to readapt to that philosophy.  One step forward, two steps back.  At the end of the 2008 season, he’ll be faced with a similar decision he faced in 2005, whether it is worth working for an organization that won’t stand behind his decisions, that doesn’t allow him to run a team entirely the way he sees fit, but will sidestep him, overrule him, upset the balance he is trying to create to attain success.

It took a complete reversal of philosophy to bring Cashman back the first time.  If Hank Steinbrenner is more than just bluster, it may take a lot more to keep Cashman this time.

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