As I have mentioned, Dugan had three prostitutes under his control. Red Maggie, Lily, and Bridget were all very nice girls, but each one was as different as imaginable from the other two. Red Maggie, plump and jolly, and so named because of the mass of wild red curls on her head. In the right light, you would swear that her head was on fire, and (as I would learn later) when her drawers were down you would swear the fire had spread between her legs. Lily was petite, under five foot I would say, with black hair and dark eyes. It was impossible to determine Lily’s true age. She was probably at least as old as me but would dress as a schoolgirl or a flower girl on the street, appearing no older than twelve years. A surprising number of men—and wealthy men at that—are attracted to girls of that age. The third was Bridget—blonde, slender and stern to a frightening degree (there are men who fancy this as well.) Bridget was the oldest and managed the other two in Dugan’s absence. She had known him back in Ireland and was the only person in Five Points to call him by his given name, Eamon. She saw herself as Dugan’s girl, and would sometimes share Dugan’s bed, sending Jack and me into the hall to sleep. They say Bridget had been very pretty before Dugan broke her nose, but I never learned the story behind that.
There was no fanfare when Jack’s true gender was revealed; one day there was Jack the boy, the next there was Jackie the girl. The whores were more upset about this than anyone, not knowing exactly how this change would impact their lives. They had always been sweet to me, but cool towards Jack, as if they sensed something was not right. Now that she was a girl, they were openly hostile towards her and even friendlier to me.
The night Dugan caught us in his bed was soon filled with shouting. Now that he had a new woman in his crew, Dugan began formulating plans for her. But Jack would not listen to any of his ideas; she was sure that whatever he proposed, however clever, would result in her ending up a whore and she would have none of it. Dugan pressed her to listen, but he had other matters to shout about as well. Now satisfied that no unnatural acts had been performed in his bed, Dugan became angry that we had used his bed for our natural sex acts and he wanted to slap us down again for even thinking of it. But in the end, all of these arguments led nowhere, so, leader that he was, Dugan suggested we all go to sleep and resume the discussion, with clear heads, in the morning.
The next day Dugan asked Jack if she had any female attire. Reluctantly she showed him the dress I had bought her in Albany. It had been balled up in her haversack since the steamboat.
“That will do nicely,” he said.
“I ain’t whorin’,” Jack said.
Dugan patiently explained that what he had in mind was beyond the ability of an ordinary whore because it required intelligence and deception—qualities he knew Jack to possess. It was called the “badger game,” and it involved a woman pretending to be a whore, and bringing a man back to her room. But before anything transpires, another man bursts into the room claiming to be the woman’s husband. He threatens to expose the man to the police, or expose him to his wife, or just to beat him to death on the spot.
“Faced with those alternatives, you’d be surprised how receptive the man becomes to the notion of a large financial settlement,” said Dugan.
“But I wouldn’t do any actual whorin’?”
“Of course not, Jackie darlin’,” Dugan said, “I’ve regular whores for that. What I need for this is a girl with brains.”
Jack continued to resist, but Dugan was relentless. Finally, Jack agreed to try it once.
“Brilliant.” said Dugan, “Now take that dress to the Chinaman to get washed and pressed. We’ll get started tonight.”
That evening Jack put on the dress, and we all went to a grogshop on Orange Street called the Diving Bell, where Dugan explained the details of the badger game. The game was very simple, but the hardest part for Jack was getting beyond her boyish ways. Though wearing a fancy dress, she would lounge in the most unladylike positions. Dugan had to school her on keeping her knees together and adopting a more feminine attitude.
“You don’t have to be a proper lady, Jackie, but you don’t want to scare them away either,” he said.
Jack told him she had her own way of doing things and guaranteed she would have no trouble getting a man interested. In Dugan’s plan, she was to find a man in Pete Williams’s dance hall, further down Orange Street and bring him back to a room he had arranged in a nearby house of assignation. The dance hall was a popular spot among men who came from uptown to experience life in Five Points; “going slumming” they called it, and to Dugan, they meant easy money.
Dugan took me to a small and simple room on the second floor with just a bed, a chair and a little table with a lamp. In one of the walls was a sliding panel and Dugan showed me how to hide behind it to watch all that happened without being seen. Then he went downstairs to wait for Jack.
Jack was right; it wasn’t long before she entered the room with a man. He appeared to be clean and well-dressed, at least by Five Points standards, and probably about fifty years of age. No sooner did he shut the door when he started embracing and kissing Jack. He had his hands all over her and was lifting her skirts, trying to get his hand under them. Then the door burst open and in came Dugan.
“What’s this? What the hell are ya doin’ to me wife?
The man jumped in fright and pushed Jack away from him. “I didn’t know she was your wife, mister.”
“Did ya think she was your wife, the way ya were handlin’ her? Maybe your wife would like to hear about this, or maybe I’ll just kill you meself.” Dugan raised a fist, and the man cowered in fear.
I think it was the gentleman who first mentioned money, offering Dugan a hundred dollars to forget the incident.
“I’ll take all that’s in your wallet.” Dugan said, “Consider yourself lucky ya got off so easy for molesting a man’s wife.”
The man gave Dugan his money, showed him that his wallet was empty, then ran out of the room. He must have been a traveler, come to the city on business, for he left Dugan with at least two hundred dollars. Dugan had high praise for Jack’s ability to hook a fish of this size. But lucrative as the game was, Dugan had no intention of spending his nights playacting; that time was already committed to drinking, fighting and carousing with the Dead Rabbits. He wanted to try the game with me playing the husband.
So I waited outside the house, and, once again in a surprisingly short time, Jack returned, arm in arm with a high-toned gentleman. He wore a tall hat and the diamonds on his watch fob sparkled in the light from the streetlamp; I could already picture the size of the man’s wallet. But when the time came for me to play the cuckold, I had neither Dugan’s acting skill nor the imposing threat of his height and girth. I feigned anger and said all the same things that Dugan had, but rather than bargaining for his life and reputation, this man opted to shove me aside and bound down the stairs. I followed after, but by the time I reached the street, the man had disappeared, and I had no idea in which direction he had run.
“You just ain’t got the stuff, Jonathan,” Dugan said to me when I was back upstairs. “And there’s nothin’ more pathetic than watching a man attempt a job he ain’t suited for. I’ll get one of me other boys to play the husband.”
“No,” said Jack, “I won’t work with any of them idjits.”
Since revealing herself as a woman, Jack had been receiving unwanted advances from some of Dugan’s men. She wanted no part of a venture that might encourage them further.
“Alright, we’ll try another game,” said Dugan, “Not so elegant as the badger game, but just as profitable. And well within Jonathan’s ability.”
Dugan taught us the panel game. I would hide behind the same panel in the wall that had shielded me before and wait until the man removed his clothing and got into bed with Jack. Then I would quietly sneak out of the wall, find his wallet, remove the contents, and return to the hole in the wall, sliding the panel back.
The game proved quite easy for me when we tried it; I came back with a nice wad of bank notes. But Jack did not like the panel game at all. In order for me to steal his money without being seen, Jack had to distract the naked man in the only way that made sense. And once my work was done, Jack would not be done with hers until her partner was done with his. What Dugan had failed to mention was, there is no way to play the panel game and avoid confrontation and violence unless Jack allowed the man to have his way with her—completely.
“I ain’t doing that again,” Jack said when Dugan came in to pick up the money.
“I don’t know why not,” Dugan said, “we’re makin’ some big scores here.”
“You’ve got me fornicating with strangers, Dugan, and if that ain’t whorin’, I don’t know what is.”
“It ain’t whorin’ Jackie; it’s stealin’.”
“Well, they’re still fuckin’ me for money and I ain’t doing it again.”
“Sure,” said Dugan, “I’ll get Jimmy to play the badger game with ya.”
“No,” Jack shouted, “I told you I ain’t working with any of your men. I want to go back to picking pockets. What do you say, Pratt?”
“I think it should be up to you, Jack,” I said.
Dugan gave me a smack in the side of the head and said, “It’s never up to the woman, Jonathan, you should know that. We’re makin’ too much money to stop.”
“I ain’t doing it anymore,” Jack said.
“You are. That’s final.” Dugan said.
Jack gave me an imploring look as if I should stand up to Dugan and put a stop to this. Then Dugan looked at me too, standing with his fists on his hips, waiting to see what I might try. But what could I do? If I put up a fight, Dugan would just knock me down again and get what he wanted anyway. I just looked at the floor.
“Fine.” Jack said at last, “But I’ll do the stealing myself. I don’t want you or Jimmy or Pratt or anyone else in the room with me.”
And that was how it started. Though she always called it stealing, and she never associated with any of Dugan’s prostitutes, Jack had become what she had vowed she would not. Dugan had made her a whore, and I had done nothing to stop it.