Pope's Memoirs: Working With Whitey

Growing up in the state of Massachusetts is hard. Mostly because at some point, Whitey Bulger is going to come up to you on the street and tell you that you work for him now. And you, being five years old, will presumably be fine with this.

I vividly remember the day of my induction into the Winter Hill Gang. It was a bright, chilly morning in November, and I was playing in the middle of the street outside our house in Springfield, the Micro Machines set I had just gotten for my fifth birthday sprawled across the pavement. One of my tiny trucks did a sick-ass flip off the side of a parking garage ramp and landed a few feet away, slowly rolling to a stop against a man’s shoe. I hadn’t noticed him there until now. He bent down to pick up my incredibly bitchin’ diminutive dump truck and its spilled cargo. He handed just the truck back to me with a confident smile, saying, “Here ya go, ked.”

“Um, thanks,” I replied and quickly returned the truck to the depot where the damage it suffered in the incident could be repaired, returning it to its task of delivering pico-pallets of an unknown orange solid to the other side of the road. There were puny people there desperately awaiting those containers, and my dump truck and I had been the only ones who stood between them and an untimely demise from a lack of orange stuff, until this man showed up.

“So you like playin’ delivery man, do ya?” He looked like a nice guy. I mean, he was smiling. Bad people don’t smile that much. It was the first time I had ever heard a Boston accent, but I didn’t have time to think about that. The villagers needed me.

“Yeah, but it’s not playing. These people need those orange crates.”

His face became very serious. “Oh, I’m sure they do.” He rolled the crates between his fingers like dice and smiled again. “Looks like we’re at a bit of an impasse here.”

I had no idea what impasse meant, but I needed those fucking crates. “Can I have them?” I said and quickly remembered to add, “…please?”

He crouched down and looked me levelly in the eyes through those thick glasses. “Well, sure. What are they worth to ya?”

This question made no sense to me. Was he indifferent to the suffering of these innocents? How could this man be so cruel and heartless as to ask such a question amidst the cries for help of the poor villagers? “I don’t know. A lot?”

“Good.” His smile spread, and I learned that this was not the smile of a friendly man at all. This was a sneer. He stood up and dropped one of the five orange crates into my hands below.

“You can pick up the rest when you’ve earned them,” he said as I quickly brought the crate into the loading bay, just seconds after the truck was exiting from the repair depot and ready to make its urgent delivery. “We’ll see you down at the old match factory on Monday morning.”

As he walked away and I steered the truck at a dangerously high speed through a number of infinitesimal intersections, I hoped that just one crate would be enough to save everyone until I could get the rest. And I wondered about what kind of work I would be doing for the balding man.

Just a few months after that I was busting down doors and kneecaps in Southie. I knew what I was doing was illegal and immoral. But I couldn’t stop. The microscopic men and Lilliputian ladies of the village would need as many orange boxes as possible to make it through the winter. Twelve had already died painfully since that first meeting with Whitey. I could live with the things Whitey had me do, but I couldn’t live with the deaths of any more villagers.

Sixteen years later, I came to the realization that the villagers didn’t actually exist and I had been paid to do terrible and criminal things in puny plastic pallets painted poorly to look like wood for most of my life. I decided it was time to quit and get a real job.