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Chapter 14

Students of Thievery; In Flagrante Delicto.

The day after our disastrous first tries at stealing in Five Points, Dugan gave Jack and me lessons in big city thieving. He had come back from the church a changed man, ready to help us correct our errors rather than berating and punishing us for them.

“I had planned to come home and murder you both,” he said, “and drag the corpses into the hall to be discovered someday by someone else. But Father Flynn was so forgivin’ of me, happy just to have his statue back, that I thought I should forgive as well. After all, it was me own fault, sending a couple of farm boys out to steal in the city.”

He taught us then how to pick pockets. Putting on a coat and vest, he coached us on removing a wallet or watch from a pocket without being detected. We practiced doing a simple collision of pedestrians, taking advantage of the momentary confusion to dip into our mark’s pocket. Working in pairs was also effective, with one asking the mark for directions and the other stealing his goods. When Dugan thought we were ready—and it wasn’t long—he took us out to try it on the streets.

We boarded a Fifth Avenue streetcar—the car that carried the brokers and bankers between Wall Street and their homes uptown.  When we were positioned in the full car, Dugan would announce loudly, “There are pickpockets aboard; my wallet and watch have been stolen!”

The men on the car would instinctually feel for their own wallets and watches to make sure they hadn’t been robbed. With this information, Jack knew where to look for each man’s valuables. She lifted a man’s wallet, secretly handed it off to me, I got off the car at the next stop, and we were all safe from detection. Jack and Dugan got off then and took the next car back. I got on, and we played the trick again traveling in the other direction, this time with me stealing and Jack receiving. After several successful trips, Dugan took the wallets and left us on our own, satisfied that we were now competent thieves.

Jack and I soon became accomplished pickpockets, working sometimes together, sometimes alone. In addition to the streetcar, we practiced our trade at funerals, political rallies, restaurants, even outside the church on Sundays. Dugan had no problem with us robbing from churchgoers as long as we stayed out of the church itself. Whenever a crowd gathered, Jack and I would be there.

Dugan could not have been happier with us. We were bringing in so much money for him that he could let us keep a sizeable amount. We had earned his trust, and that of the other Dead Rabbits, and could now travel freely in and out of Five Points. Jack and I had grown close once more; we worked well as a team and also spent time together when not working. We would go to plays at the Bowery Theatre and sometimes the theatres on Broadway. Jack liked the Shakespeare plays best, but we saw melodramas as well, and variety shows that were little more than dancing and singing. They were just fine for me. Sometimes we would go for a drink in one of the big Bowery beer halls, or any of the Five Points dives. They provided plenty of entertainment, as long as we minded our own business and stayed out of people’s way.

Things were going so well that I had lost my urge to leave the city. I enjoyed picking pockets and felt no moral qualms about doing so. It was like flogging that poor sailor on the Eastern Star, I was not stealing from these individuals, but from the world of people who prospered while pushing me down.  I loved the danger of it as well. I was very careful about lifting the goods without getting caught.  But in the unavoidable cases when I was caught, I was never again without an escape plan. I would disappear down dark alleys where no sane man would follow.  I had become a professional thief, and it pleased me.

But if there is one thing I have learned from bitter experience, it’s that when all is well, and your life seems nothing but clear skies and sunshine, take warning. The winds are about to change and storm clouds gather just beyond the horizon.

I came back to the room one evening to find Jack lying under the covers on Dugan’s mattress.

“Jack,’ I said, “what are you doing? Where’s Dugan?”

“He’s out,” she said, “He won’t be back for hours. The Dead Rabbits are fighting the Plug Uglies tonight.”

The Plug Uglies were another Five Points gang, one of the toughest. They were all huge men, most over six feet tall, and distinguished by the tall plug hats they wore, stuffed with leather and rags, to protect their heads when fighting. They always went into battle heavily armed with clubs, brickbats, and pistols. Periodically they would fight with the Dead Rabbits, usually in Paradise Park, over some perceived insult or someone stealing a girl from an opposing gang member. The battle would likely rage for hours and, win or lose, the Dead Rabbits would spend the rest of the night drinking and recounting their exploits.

“Come lie with me, Pratt.” Jack sat up and revealed herself to be naked under the covers.

“I don’t think that is a good idea, Jack.”

“Come on, Pratt, Dugan is gone for the night. It’s been such a long time; don’t you miss it?”

Well, it had been a long time, and I did miss it. And if Dugan was out fighting the Plug Uglies, we were not likely to see him until the following day. I took off my clothes and got under the covers with Jack on Dugan’s straw tick.

Jack had been so thorough and studied in keeping her true gender a secret from Dugan that I, myself, had nearly forgotten that she was a girl. I remembered right quick. We had not shared a bed since our last night in Albany, and we went at it like alley cats. Jack’s screams of pleasure as the passion mounted were so loud and forceful that, had we been anywhere but the Old Brewery I would have feared alarming the neighbors. Then, just moments later, we lay spent and sweating, side by side.

“We have to get out of here, get our own room somewhere,” Jack said.

“Somewhere outside the Old Brewery,” I said.

“Somewhere outside of Five Points, Pratt, in my opinion.”

“I don’t think Dugan will allow that.”

“To hell with Dugan,” she said, “We’ve repaid our debt—fivefold at least. If we don’t leave him behind, he’ll have us here forever. We ain’t like those other idjits working for him; we’re smart, we know the ropes. It’s time to move.”

“It won’t be easy,” I said, “It will take some care.”

“I’ll show you some care.” She said, throwing a leg across mine and we were at it again.

Then, at the most inopportune time imaginable the door burst open, and Dugan bounded into the room. The sight of us lying together in his bed stopped him dead in his tracks.

“Jesus Chroist,” he shouted, “What’s this then? Me own men engaged in unnatural acts in me own bed!”

“It’s not what you think,” Jack said.

“I knew from the start there was something peculiar about you boys, but I didn’t reckon on this. Just a couple of buggerin’ sissies.” Dugan came towards us with murder in his eyes.

“It’s not you think, Dugan. It’s nothing unnatural.” Jack sat up then and threw off the covers. Dugan stopped short again, experiencing his second great shock of the evening.

“Sweet Mother of God, you’re a girl!” He stood there aghast. “Ya been a girl the whole time, hain’t ya? And I didn’t see it. This changes things. This changes everything.”

“It don’t change nothin’,” Jack said, “Tomorrow I’ll be the same person I always was. Nothing changes.”

“Shut up now, missy, I’m trying to think.” Dugan stared at Jack, stroking his chin.

“Nothing needs to change, Dugan. I’m as good as any of your men, ain’t I? Better in fact.”

“That’s what has me thinkin’.”

“So I’ll stay a boy; no one’s the wiser.”

“Lassie, will ya put your blouse on, please.” Averting his eyes now,  “We’ve business to discuss.”

“I’m not whorin’ for you, Dugan.”

Oh, there’s plenty of ways for a smart lass bring in money short of whorin’.  Plenty of ways.”