Tommy Gerolli: Millionaire, Playboy, Gangster

In this story, we see through the eyes of "Tommy", an innocent kid turned gangster and his rise to power. It's a story of sex, drugs, guns and betrayal... and Tommy loves every minute.


1. My Father

My father was a great man. I remember every detail of his face, his crooked nose, his dull eyes, every rough patch and wrinkle he had, the man seemed like an old geezer but he was built like a brick shit house.

 He taught me everything I know today, from how to shoot to how to respect women, the big man knew it all, it seemed he had this infinite book of wisdom he had stored away. If I had a question, he’d answer it, and no matter how vague or confusing his answer was, he’d always find a way to make me understand.

 My father was involved with the notorious gang: “The Tortelli family.” He never spoke his past but it wasn’t hard for me to find out. After all, the Tortelli Family was the talk of the town, anybody who was remotely involved with them was thought of as a local hero.

Although he never made much of a name for himself within the mob, he was trusted enough for the family to allow him to be involved with some big-time weapon deals, leading him to make some serious cash… And some serious enemies.

I don’t remember much of my mother, from what my father told me, she was a gorgeous woman, long blonde hair, piercing blue eyes, and a voice like velvet. He always told me that my mother had died giving birth to me, but I knew the truth. All the other kids on the block told me the rumours that their parents had told them, she had died because some sick scumbag had wanted to teach my father a lesson. I had always wondered if this is why my old man quit the business.

The earliest memory I have of my old man was when I was about three years old. He had left me with a buddy of his in our apartment so he could “run some errands”. After about an hour he came bursting through the door, sweat poured from his face and I distinctly remember a great sense of fear in the room.

“Teddy!” he shouted to his friend. “Grab the fucking piece and take Tommy in the bedroom.” Teddy looked at me and took me and took me by the hand and led me to the bedroom.

“Wait here, kid.” He said. “Don’t move.”

I sat on the floor and stared at the door. After about five minutes I heard the door slam and shots went off. The shouting and gunshots seemed to go on forever and finally, they stopped. My father came into the bedroom and stared at me, blood on his face, out of breath, and trembling.

“It’s okay Tommy, everything’s going to be okay...”

He kept me in the room for another couple of hours while I assume Teddy was clearing up. When he finally let me out the three of us sat in the living room in silence, nobody said a word, until my dad burst out in laughter.

“Shouldn’t have fucked with us, eh Teddy?”

“You can say that again, boss.”

I mentioned my father taught me how to shoot. On a hot summers day, we were getting ready to go out when he kneeled in front of me.

“Tommy.” He said “You’re growing up now, almost twelve years old.”

“That’s right, dad.”

“Well, I’m not going to be around for all of your life. You need to be able to take care of yourself.”

“I can take care of myself!” I said with a grin.

“I know you can, son.” He laughed and ruffled my hair. “I’m talking about really being able to take care of yourself. You know, if you get in some deep shit.”

He lifted his shirt and tapped a gun he had tucked into his waistband.

Me and my dad then left the apartment, he took me to a seedy looking bar that sat in the middle of a rough neighbourhood. The nylon sign read: “Johnny’s Watering Hole.” Half of the letters’ lights had gone out.

The inside of the bar was completely different, the place was absolutely packed. Men in expensive looking suits filled the place along with their expensive looking wives. My father led me by the hand up to the bar, shaking hands with everybody he came by, sharing a quick word of two with them.

When we got to the bar, the bartender asked my dad what he would like.

“I’ll have a whiskey on the rocks.” He said “Also, me and my kid here need to use the basement.”

The bartender nodded and gave my dad his drink, without taking any money. He then passed my dad a set of keys and we moved toward the back of the bar through the crowd of people.

We eventually came through the back door and into an alley, on the far end, beer bottles had been set up on top of some crates and smashed glass covered the floor surrounding them. My dad positioned me behind a chalk line about ten feet away from the bottles.

“Hold this.” He said as he produced a Colt 1908 from his inside jacket pocket. I took the gun in my hands. I remember the way my hands shook from sheer excitement at the thought of holding my first pistol.

My dad kneeled behind me, took my hands into his and rested his chin on my shoulder.

“Hold it steady now, keep your chin up.” He whispered, bringing his hand under my chin and propping it up slightly. “Now, close one eye and bring the sight level with that middle bottle.” I did as I was told, he cocked the gun back for me. “Now, take a deep breath.” I inhaled deeply. “Pull the trigger.”

I squeezed the trigger, the gun gave a little kick and I heard the bullet whizz through the air, a loud bang filled the air along with the smash of a bottle.

My dad looked at me impressed.

“Well done son!” He cheered with a huge grin on his face. I smiled a little too.

This became routine for a few weeks. We’d go to the bar, my dad would order a whiskey, we’d go to the back alley and shoot a few bottles and then we’d go home. I became decent with the pistol after a month. I’ll never forget those few weeks I spent practising my aim with my father. Although our bond was strong, our little hobby brought us closer together than ever.

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