Michael: A Dangerous Game

Michael zigzagged his way through Milwaukee’s eastside. With a pleasant breeze at his face, he walked with an air to his step. He figured that it was maybe twenty blocks to “Checks Cashed” where he was going to make a call to Jennifer to update her on how the meeting went. That would give him plenty of time to shake any tail as he cut through alleys and parks and down side streets. Whether it was members of the outfit and the boss he had just met with, or members of the law and Cas who he had struck a deal with at the police station earlier in the week, Michael knew he was being closely watched.


Jennifer, or Jen as Michael affectionately called her, was the longtime girlfriend of Rory, who was Michael’s old friend and running partner. After Rory passed years earlier, their crew had splintered and it was around that time that Michael decided to leave Milwaukee and head out west. In their heyday, Jennifer was an asset to their crew with her Sicilian roots, good looks, and an ear always to the street. She had dark features and a bright captivating smile that could bring down the defenses of the hardest men. While Michael and his fair-skinned boys had distinctly Irish and eastern European ancestry, Jennifer kept a year-round tan even during the dreariest Wisconsin winter months. She could easily pass as having Latin blood, South American roots, or ties to a slew of other foreign nations.


After ducking into “Checks Cashed,” Michael picked up a phone off the wall and turned to face the dingy lobby. The room was largely empty aside from a row of chairs and a few ragtag people making their plea to the ladies behind the bulletproof glass in charge of the money services. Opposite the counter, Michael could see that outside Brady Street was buzzing. Groups of tipsy revelers hopped from one bar to the next and couples walked in tandem, others with their dogs, soaking in the last remaining rays of sunlight.


“Hello?” a chipper voice said from the other line.


“Hey, Jen, it’s me.” Michael said in a deep, muted tone.


“Well, get it out! It must’ve gone okay, right?! Jennifer fired back.


“I’m still here so that’s something.” Michael replied. “Looks like I’m working for both sides now. I’m going to need some help though.”


“Anything, you know I’m here, Michael.”


In the criminal world, as in poker, you must never reveal all the cards that you hold. In order to best your opponent, you have to keep them guessing. Michael grew up around shadowy figures, many gamblers in their own right, so at an early age he learned to read past the crocodile smiles and friendly eyes. No matter what the stakes were, whether playing for chips or gambling with your life, the people who came out on top displayed the same qualities; patience, discipline, fearlessness, and of course the right amount of luck.


Michael knew that his dad’s old acquaintance, now a police sergeant, understand games of chance. After all, you don’t get the name “Big Casino” without spending enough time in smoky poker rooms grinding it out with other players. Michael knew that Cas applied those lessons learned from his gambling days to his career in law enforcement. When Michael was down at the police station following the incident at the apartment, Cas used his leverage to get Michael to agree to help him build a case against the local outfit. While he may have pitched it as a way for Michael to save himself, Michael knew better; Cas was out for a promotion and early retirement.


Before Michael went to the Pfister, he had contacted Jennifer and told her about the dilemma he was in. He knew that time was of the essence after he had shot the intruders back at his apartment. Cas told him in the interrogation room that night, that the two men had ties to the local outfit. He promised to keep the police report sealed while Michael helped to infiltrate their organization. But Michael knew that everyone had cards they didn’t want to show and he didn’t know how much Cas actually knew or whether or not he could actually protect him.


Knowing he had to act fast, Michael wanted to get in as close as possible so he had went straight to the Pfister after talking with Cas, not knowing if he was going to make it out alive. He kept Cas at a distance so he had no back up. Only Jennifer would’ve known the last place he visited. Michael was shocked that he was given sit down with the boss, or at least a close underling. He could have been killed immediately at the wave of a hand, especially if Cas wasn’t able to seal the report and the boss found out Michael killed two of their members. Fortunately, at least on the surface, the meeting went well and now Michael was on assignment from both sides of the law. This was the ultimate dangerous game and Michael knew it was going to take more than luck to come out on top.

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