I used to work for a large company based out of South Boston, MA. If you have seen “Good Will Hunting” or “The Departed” or the cinematic masterpiece “Southie: The Toughest Neighborhood in America” (starring a baby-faced Will Arnett and Kickassachusetts native Donnie Wahlberg), you know that Southie is a haven of beer-drinking, Red Sox cheering, outsider-hating Massholes. It’s heaven.

For a few years I lived and worked in Southie and loved every minute of it. The beach, the bars, the boys covered in Celtic tattoos—it was my personal heaven.

I could walk to work (E street to A street), I could generally wear whatever I wanted, and I enjoyed my job overall. The work was interesting and the people were fantastic. I was an Editorial Assistant for a small educational publishing company that was part of a larger, multi-national conglomerate. My office was mostly Massholes with a few New Hampshire “Live Free of Die” types thrown in. Like “The Jersey Shore,” only with pastier complexions and accents that transformed words like “beer” into “beeya.” We partied hard at the Christmas party and summer outing, had an annual company trip to Fenway Park, and we’d wear Red Sox/Patriots gear to work. The staff of this company was comprised of people who were, in essence, Mass townies.

Our CEO wasn’t beloved, but he was pretty popular. Cool guy who would throw down beers with the best of ‘em. You know that you work with a bunch of townies when a boss who drinks hard is synonymous with a boss who deserves respect.

So you can imagine our surprise one Friday morning in the summer of 2005 when we arrived at work to see an email informing us that our CEO was “no longer with the company” and we were to report to the cafeteria at 10:00 am for a company-wide meeting. Everyone was stunned and anxious—were they going to shut us down? Was the entire company completely unstable, or was this just a change at the top?

We arrived at the cafeteria and took our seats in front of a podium on which rested a microphone and a Red Sox baseball hat. I figured that somebody had just left it up there—this space was used by lots of different groups within the larger company. Then the head of HR stepped up to the podium and explained that we were all gathered to meet our new CEO, a man I will call Greg B. He ran the office in Albany, NY and would now be overseeing both the Albany, NY branch and our branch in Boston, MA.

Out of the cafeteria’s back entrance walked a 50-something man in a New York Yankees baseball hat. We all sat in silence. Huh? What was going on here? I immediately assumed that he must be some random asshole who was cutting through the cafeteria (a common occurrence) and his timing was just sucky. That couldn’t POSSIBLY be our new CEO, as nobody is stupid enough to try and win over a staff of Bostonians while wearing a Yankees hat. That would be wholly moronic—to wear a Yankees hat in a building where they literally FILMED “The Departed” (the abandoned building off of which Martin Sheen falls to his death—that was literally the cafeteria of this office) and attempt to ingratiate yourself to a staff who just lost their real CEO. No way, right?

Wrong. This was our CEO. We sat in horrified silence as Greg B. walked up to the podium, slowly removed his Yankees hat, and dramatically put on the waiting Red Sox hat. This insane strategy to “win over the Boston office” was akin to taking a dump on an acquaintance’s front stoop in hopes that she will somehow then become your best friend forever. It boggled our collective, Red Sox loving minds. If no baseball hats had been involved at all, we all would have been sad for our former CEO, but willing to move on. But for this new CEO to flagrantly showcase such a turncoat mentality left the entire staff fuming and upset.

He didn’t last long though, as the FBI caught him with child pornography on his laptop and he is currently serving a jail sentence of 72 months in jail. So I guess that being a Benedict Arnold of baseball teams was the least of his defects.

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