“The grass is always greener on the other side.”

It’s a simple little phrase that every human being at a career crossroads encounters at least once in a lifetime.

In Theo Epstein’s case, it shouldn’t even be considered – not even for a second.

The 37-year-old Epstein has done more in his young life than most of us will do in our entire time on this Earth.

Epstein’s resume is chock-full of gold star achievements, dating back to 2002 when he took the Red Sox GM job as the youngest to ever have such a position in the history of Major League Baseball.  Two years later, he “reversed the curse” and had a major part of sending the city of Boston out of 86 years of misery, all in dramatic fashion against the hated Yankees.  Three years after that (in 2007), the Sox added another title to its rich history.

But there’s still so much more that Epstein could add to his trophy case, and plenty of reasons to do so, especially after Boston’s 2011 season result.


Some out there say Epstein comes off as very arrogant, but no one can question the success he’s brought to the Boston Red Sox since 2002

To explain why, one would have to look at the Epstein situation from a number of different angles.  First and foremost, Theo Epstein might just be one of the most arrogant sports figures in the game – and while I haven’t met him personally, I’m banking this fact on numerous unnamed sources outside of the baseball world that have had encounters with him in other social situations.  In each person’s case, they mentioned how most of the Red Sox members were actually quite pleasant, including the likes of Dustin Pedroia and yes, even the fiery Jonathan Papelbon.  But Epstein, not so much – and that point will be revisited shortly.

As most sports fans are already aware, Theo Epstein’s name has popped up in the rumor mill numerous times over the last few weeks, mainly circulating around two positions – continuing to work as the GM of the Boston Red Sox, or moving on to fill that position with the Chicago Cubs – a franchise marred in a 100-plus-year championship drought.

Days back, the report emerged that the Chicago Cubs had asked the Red Sox to talk to Theo Epstein about their open GM position.  No concrete news followed these reports, leaving the baseball world curious if Boston had given the okay for these talks to even occur.

Over the weekend, a new rumor emerged, where a Cubs fan stated that he had spotted Epstein in Lincoln Park (yes, the Chicago area, for those that are unaware), and had a discussion with him at a local Starbucks coffee shop.

Whether that rumor was true or not, no one can be sure right now – but one thing is clear, if the door opens for Epstein to take the Cubs job, then he should 100% grab that role by the horns – and for many reasons, from continuing to build his legacy, to the need for a change, and to the likely reactions from the Boston media and fanbase.


For decades, Cubs fans have dreamed of seeing the Wrigley Field sign say this after a World Series Game 7

First, it may be time for a change.  Epstein has been in the Boston role for nearly a decade, and while he’s made plenty of quality moves over the years, some of his decisions were ill advised in 2010 and 2011.  While most critics will point at the pricey additions of Carl Crawford and John Lackey, I can’t help but look at July’s trade deadline.  The Red Sox were clearly hurting for depth in its starting rotation due to a number of injuries.  But all Epstein could muster up were attempts for Erik Bedard and Rich Harden – both talents that have been – yes, you guessed it – injured for the majority of their careers.  Why attempt to fill a hole vacated by injury with another player with an injury-rich history?

Second, it’s the pressures brought on by the Boston media.  Epstein himself likely can easily ignore the constant prodding from the media, but the cries from the fanbase could get louder and louder.  The Boston sports fan is extremely passionate, much like the rest of the major market fanbases in the Northeast.  As quickly as the Boston sports fan can build a love and passion for its team, they can turn on them that much quicker, especially after a collapse such as the one that the Red Sox had in September.

And the feverish hunger generated from two World Series titles over the last seven years only makes things worse.  That hunger simply turns to more anger for each time that John Lackey gets shelled, or Carl Crawford has an ‘oh-fer’ night.  It gets to the point that the best option would be a fresh start for all parties, much like Terry Francona has already received, after being dismissed from the Red Sox manager position just days ago.

Finally, we come back to Epstein himself, and the passion that hides inside him, coupled with the arrogance that some people have been exposed to.  When you have an individual of Epstein’s mind and talents, wouldn’t it make complete sense for him to take on the Chicago Cubs GM position if the opportunity presented itself?

Plain and simple, if Theo Epstein headed to the Cubs and was able to end Chicago’s curse, too – he would easily be known as the best general manager in the history of Major League Baseball, and the man who was able to overturn two of the biggest droughts in sports history.

Ego or not, it’s an opportunity that Theo Epstein simply would have to take – and is there another more clear no-brainer in sports today?

That answer is no, and you don’t need to check the grass to know it’s true.

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