SO WORCESTER, IT HURTS…#6 by Steve Siddle

July 7, 2011 § Leave a comment

So Worcester, It Hurts… #6

The Bulger Files

by Steve Siddle

James “Whitey” Bulger was the bogeyman to young hoods in the Tri-City. Like the Keyser Soze of South Boston, Whitey’s name was a ghost story told in the corner booths of all night diners, in smoky social clubs and in shadowy parking lots. Whitey stories came with the warning given or promise made that: “This is between you and me.”


There once was a man I called “the Pope.” He was one of the last real bookmakers. A professional man in the now lost meaning of the phrase. He was trustworthy, wise as a fox, and “in the know.” He was old school in a way that had nothing to do with hip-hop.

I was with the Pope one night at the end of the bar. We were in Worcester, the summer of 1999. It was past last call; the sign was off, the stools were up and the bouncer was sweeping the broken glass. The Pope was always good to me and more than once he gave me advice that was right on the money. He was one of the first guys who really encouraged me to keep writing.

One of the last times I saw him I was walking into Mahoney’s Bar on Park Ave in Worcester, he was walking out. He hit me on the shoulder to stop me in my tracks and he stood there holding his hand up for a minute as if he were trying to recall something important. Then he said, “try to get home with no blood, or piss, or puke on your sneakers.” It was the first time anybody had ever quoted something I had written. It blew my mind to think that the he had taken the time to read one of my stories in Blank Canvas Magazine. Knowing that he would keep reading it made me a tighter writer. I did not want to waste the Pope’s time.

I asked him that same night about Whitey Bulger. He looked at me and said as matter of fact-ly as he might have said “a dollar is four quarters”, “that guy is a scumbag.”

I promised to never forget that


It is always tempting when writing about criminals to romanticize their lifestyle. As we learn more and more about Bulger’s legacy and life on the run, we must remind ourselves that this man allegedly threatened, tortured, and murdered women. He poisoned the neighborhood he claimed to protect and was a snitch.

In looking back on the Pope and researching the Bulger case the last few days, I believe that there are some lessons to be learned; lessons about who we are, where we come from and the ways in which we must choose between right and wrong.

Some folks say that Whitey’s arrest closed the book on a dark chapter of the Tri-City’s history. I suppose some have even finally found peace and closure in the knowledge that he is behind bars. But for some of us, Whitey’s arrest has shone a light into the dark, abandoned alleyways of our lives. Reminds us of who we once were, and how easy it would be to backslide.

Whitey remains a monster under the bed. The unseen presence that makes us look over our shoulder and remember, “This is between you and me.”

I never told the Pope why I had asked him that night about Bulger. I never told him what had happened two weeks prior. I never told anyone…

Learn more about STEVE SIDDLE


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