Michael gathered himself sitting at the edge of the bed in the tiny motel room. As Sports Center shouted out morning updates on an old box TV, Michael tried to visualize the next twenty-four hours ahead of him. The day before, he had talked to Jennifer and learned everything he could about the riverboat casino, located outside Chicago, where he was headed to next. As was the case when Michael went to the Pfister, he knew that he was stepping out of his element and he was nervous. The anticipation killed his appetite as the nerves gnawed at his stomach making Michael briefly stop to think about what to eat at the train station on his way to Chicago.

 

Michael had fond memories taking the Amtrak and the nostalgia almost made him feel safe. Of course those warm thoughts quickly gave way to the frigid reality of the situation, but this was the part of the journey Michael wanted to believe would be easy. After all, he figured that the groundwork had been laid and that he had done enough convincing, on both sides that he could relax for the moment out in a public setting. He wanted the local outfit to see that he was playing ball and following their orders. And after talking to Cas last night, who reluctantly agreed to Michael’s trip, Michael knew that he had set it up as best he could and that he had better odds of pulling this off without interference from Milwaukee PD. That thought brought calm to him when suddenly the phone rang, his ride was out front.

 

Passing by a sign for I-43, a highway he had taken a thousand times with Rory, Michael recalled a conversation he had with his friend. Rory was a true hustler and entrepreneur and was making more money than anyone at the high school that had all but given up on him by his senior year. By the time Rory stopped showing up to class, Rory was supplying his school and a dozen others with alcohol, weed, pills, cigarettes, jewelry, electronics, pretty much anything illegal, or legal and cheap, one could want. He was even breeding dogs and ran a landscaping business, mostly a front to grow weed. Rory gave Michael a wealth of street knowledge. Michael, in turn, introduced him to books, music, culture, and turned him into a more refined criminal in the process. Michael thought about how their personalities complimented one another as he rode in the backseat of a large Lincoln sedan on the way to the train station. Michael recollected stories Rory used to tell, passed down to him from elders in his childhood neighborhood. He used to talk about how drugs infected old mob organizations, destroying a longstanding code of honor and loyalty, and how you had to be out for yourself now, the golden days of the mob were long over. Michael liked to remember Rory at his best, before drugs eventually destroyed him as well.

 

Having arrived in Chicago, Michael jumped off the train and wormed his way through the crowd at Union Station. He walked up a final flight of marble stairs before exiting onto bustling Canal St. Hopping into a waiting taxi, Michael gave the name of the riverboat casino to the peppy driver as the cab lurched out into traffic. Jennifer had wanted to meet up with Michael immediately upon his arrival to Chicago, but it was decided that it would be too risky in case someone was watching. Michael had lost enough loved ones to the underworld and the last thing he wanted to do was get Jen caught up in his mess. She had gotten away from a lot of bad influences back in Milwaukee and was now working at a chic clothing store and attending night school. Still, she had jumped at the chance to help Michael when he called to inquire about Milwaukee’s outfit doing business in Chicago. She still had an ear to the street and had connections to the casino where Michael was ordered to go from the boss at the Pfister. Jennifer told Michael to look for an Asian bellhop with black, slicked back hair, but he would probably be wearing a kitschy hotel outfit and cap. Jennifer said that he would be expecting Michael and would be giving him instructions on where to go next.  

Michael: Gangland Chicago