Dugan was the epitome of a Five Points gangster—words that meant nothing to me when I first heard them but which soon took on great significance in my life. As Jack had told me, Dugan was a member of the Dead Rabbits, a gang of rowdies who controlled Five Points, the neighborhood where we now lived. He wanted us to call him “Slasher,” an appellation he earned by slashing a rival’s face with a razor, but everyone else just called him Dugan, and soon Jack and I did likewise. Dugan was about twenty-five years old, with side whiskers nearly to his chin. He wore a soft hat, cocked at an angle; his sleeves were always rolled to the elbow as if too narrow to house his massive forearms. Red suspenders held up his trousers and on his feet were hobnailed boots. Tall, strong, and quick to anger—as I can readily attest—Dugan liked nothing more than a good fight and would indulge in that pastime quite frequently, either man to man, or in gang fights joined by other Dead Rabbits.
He told us we could live with him, until we got settled elsewhere, in a building known as the Old Brewery. If there is any structure on earth more filthy, more vile, more vermin-infested; with more degenerates, thieves, and libertines calling it home, I pray that I will never see it. In earlier times the huge three-story building had served as a brewery, but now it was divided into single, windowless rooms. Sometimes three or four families would inhabit one room, their cook fires filling the halls with smoke, and their wailing babies interrupting our sleep. Young men ran wild through the halls, entering any unlocked door, and stealing anything not clutched tightly by its owner. From fights, beatings and rampant promiscuity, screams would resonate through the halls at all hours. Dugan had one room to himself and even had a straw tick to sleep on, making him part of the Old Brewery’s aristocracy. Jack and I slept on the floor of his room.
When in a bright mood Dugan was not such a bad fellow. He shook my hand when I returned to his room with Jack, and he forgave me for putting up a struggle aboard the ship. Jack had convinced him that we were notorious pirates from the Erie Canal, and he was duly impressed by our reputation. It was clear that he hadn’t the slightest notion that Jack was a girl, in fact, he no doubt thought her more a man than I was.
“Jack tells me you’re a good man to have in a tight spot, Jonathan.” Dugan said to me, “I don’t see it meself, but I’ll take Jack’s word.”
Dugan explained his business to us. He had a crew of four or five thieves, tough as he was, but not as smart, who would bring him a cut of everything they stole. Every week he or one of his men would visit the local merchants and offer them the opportunity to pay him tribute rather than have their businesses destroyed. He also managed three prostitutes.
“You’ll see ‘em stopping by at odd hours to pay me my due.” He said, “You boys keep your hands off of ‘em unless you’re payin’.”
“What about the cider?” I asked, wondering where that fit into his business.
He laughed. “The cider was but a whim. I got a cravin’ one night for cider, having not tasted a glass since I left Ireland, but nary a dive nor tavern nor grogshop in Five Points offered cider for sale. I sensed an opportunity so arranged with some men upstate for two deliveries. Well, you’ve seen the second delivery, and we haven’t yet drunk up the first. Sure they’ll take the barrels as a favor to me, but there is a limit even to that. It was me own mistake, I’ll admit. The city has thirteen breweries and at least three distilleries. When yer aflood with barley who wants apples? Still, if I ever gets the cravin’ again, I’ll have me cider.”
He had somewhat less forgiveness for the mistakes of others.
We soon got down to business and Dugan explained what he expected of Jack and me. We were both in his debt for the rescue and for the privilege of sleeping in his room. We were to repay him by stealing and bringing him the proceeds; it was only natural, robbery being our professed occupation.
“How much must we steal to be out of your debt?” I asked.
He scowled at this. “Oh, you don’t want me putting a number on it, boyo, it may be higher than you can count.”
I could tell he had little faith in me and I was trying his patience. He proposed that Jack and I go out the following day but go our separate ways, each stealing what we can, then at the end of the day he would be better able to assess our worth. I’m sure he wanted to see what I could do without Jack’s help.
So the following day Jack and I separated outside the Old Brewery and began our lives as Five Points thieves. It seemed an odd place to begin thieving with everyone in the neighborhood so poor. I thought of improving my chances by looking for a more prosperous neighborhood, but I remembered what Jack had said about the Dead Rabbits. If even half of the idle fellows standing on street corners, who eyed me suspiciously as I passed, were Dead Rabbits, I stood little chance of leaving Five Points.
I was not sure where to begin. Though by this point I could honestly say that I was a thief, my experience was really rather limited. In fact, the only thing I had ever taken from someone against his will was the money I took from Lucas Ramsey’s vest. And that wasn’t even his money. There were shops along Canal Street which had money and goods I might be able to grab. Occasionally I saw a well-dressed man walking down the street; I considered the prospect of snatching a watch chain and running. It all seemed too dangerous to undertake without a little planning.
I decided to start small, just to get the feel of the thing. As Jack had described so long ago when we first planned this trip, there were men selling vegetables and fruit from carts on the street. Crowds of people were everywhere, shopping or just walking briskly up and down the streets. I saw a cart piled high with apples and I thought it would be the easiest thing in the world just to grab one of them and blend into the crowd. I snatched an apple and turned away quickly, hoping to move unseen into the passing crowd, but I had not looked where I was going and bumped into a large man who pushed me away, into another man who knocked me back toward the cart. I lost my balance then and stumbled into the applecart, pushing the whole thing over, spilling apples into the street.
As I lay on the pavement, the owner of the cart began beating me with a cane and yelling at me in some foreign language. This got the attention of a police officer who had been chatting with a young lady by a dry goods store. He had a stick as well, and I was afraid he intended to take a turn at beating me. Instead, he pushed the vendor away and poked me in the ribs.
“On your feet, boy.” He said, and I complied. “Did you do this?”
He pointed with his stick at the overturned cart. The apples on the ground had attracted the attention of dozens of barefoot children who grabbed as many as they could carry and rushed back into the alleys.
“He steal my apples!” the vendor shouted, with a thick accent.
“I’ll take care of him.” Said the policeman, and with an iron grip on my arm, he marched me to the police station.
“What have we here?” asked the desk sergeant when we entered the station.
“Stealing apples and me not five feet away.” Said my captor, “Do you recognize him?”
Of course, the sergeant did not recognize me, nor did any of the boys in blue who seemed to be lounging idly at the police station.
“We’ve new ones arriving daily; brazen thieves, all of them,” said the sergeant, “We should make an example of this one, thinking he can do his thieving within eyeshot of an officer. Take him to The Tombs.”
They put me in a black police wagon, and we traveled just a few blocks to The Tombs prison. The Tombs was a huge building of grey stone, with four thick columns in front, looking like an ancient temple to a vengeful god. The policemen took me in a side door, signed some papers, and left me with a man of a different uniform who walked me to the second floor and down the aisle. The cells were against the walls of the building, and the narrow hallway in front of the cells had railings on the other side and overlooked the vast empty center of the building. The arrangement was such that a guard standing on the first floor could look up and see activity on any of the floors above him.
The guard took a ring of large keys from his belt and unlocked a cell door, shoved me inside and locked the door again. The cell was already occupied by a man in rags, sleeping soundly on the only bunk. I sat on the floor, my back against the cold stone, and waited.
Through it all, I had kept my mouth shut. I thought of asking the guard how many days I must stay in the cell, but I was afraid that, like Mr. Dugan, he would quote me a number higher than I could count.