When I was in Holy Cross School, I had several paper routes and I really enjoyed delivering newpapers. My best friend in the fourth grade was Patrick McDonnell. One day he asked me to help him deliver newspapers on his paper route. One of his older brothers had the paper route, but when he got tired of delivering newspapers, he gave the paper route to his brother Patrick. In those days, it was almost impossible to get a paper route on your own. True to Chicago tradition, you even needed clout to get a paper route.
I helped Patrick deliver his newspaper, The Chicago American, for a few days. One day, he asked me if I knew who all the customers were. Of course, I did! “That’s good,” he said. “Because you can have the paper route!” He had gotten tired of delivering papers and couldn’t quit the paper route until he found a replacement. Well, I was extremely happy to be his replacement because I loved delivering newspapers and I especially loved having some spending money. I’m not sure how long I had that paper route, but it was long enough to see the Chicago American become the Chicago Today. I loved reading the newspaper as I walked door to door delivering it. Then one day, the Chicago Today folded and I was out of a job. But it was fun while it lasted.
Months later, my friend Patrick asked me to help him with his paper route again. He had found another paper route and again he was tired of delivering newspapers on his bicycle. He immediately thought of me as his replacement. This route had many more customers than the other one and you needed to deliver the papers on a bicycle because this route covered our entire neighborhood. This paper route was the most memorable one for me. Paper route number 9! I really learned a lot about life while delivering newspapers on this route. And, I also truly learned a lot about the Back of the Yards and its residents. On this route, I delivered the Chicago Daily News, the Chicago Zgoda, and the Chicagowski, the last two were newspapers published in Polish. I tried to read the Polish newspapers, but they seemed be written in a foreign language to me. And most of the Polish subscribers hardly knew English, but we always understood each other.
There were two facets to delivering newspapers. One was the actual delivery of the newspapers. Some subscribers wanted it delivered a certain way. Folded without a rubberband, or with a rubberband. On the front porch, or on the back porch. Between the screendoor and the door. There were considerate customers who didn’t mind if I just rode past on my bike and threw the paper on their front porch. And my aim was true, most of the time.
One day, as I was approaching a house next to the alley, I was about to throw the newspaper on the porch when suddenly a car sped out of the alley. I was shaken a little and when I released the newspaper, it broke the glass on the storm door. I was so scared that I kept riding and delivering papers. When I returned to the newspaper agency, the subscriber had already reported me to my boss, Ernest Pressman. I swear. That was his real name. She knew it was an accident and she only wanted me to pay for the broken window. I remember I had to pay about four dollars for a new window, roughly my weekly salary before tips.
Sometimes delivering the newspaper could be downright dangerous. One customer wanted the paper delivered in the rear hallway. What I didn’t know was that somethimes she kept her German Shepherd there. One day, I open the hallway door and saw the German Shepherd lounging at my hand that was attempting to drop the newspaper in the hallway. I quickly shoved the newspaper in his mouth and slammed the door shut. I was waiting for another reprimand from Mr. Pressman when I returned to the newspaper agency, but I was never reported for this.
The second facet was collecting the money for the subscriptions. Collecting money from some customers required an excellent memory, ruses, and strategems. All this just to collect a measly fifty cents! I had to remember what day they got paid so I could go collect the money that day before they squandered it away on rent, food, utilities, and other such nonsense. And I also had to make sure I had enough change so they could pay and I could give them change. They wouldn’t pay unless I gave them correct change.
One woman once asked me if I had change for a five. Of course, I did. So then she upped it to ten dollars. I told her I had change for a ten, too. Then, she said for a twenty and I said yes. She then told me she had a fifty dollar bill and I showed her that I had enough change. I was ready for her because she had tried this before. She then paid me in exact change and gave me a nickel for a tip. I mean I got to know all of my customers very well. One woman told me to collect the money on Saturday morning at 8:00 a.m. and then wait for about ten to fifteen minutes until she opened the door. Not a problem, I told her. All I wanted to do was collect my money, and hopefully, a small tip. The reason she wanted me to knock on her door so early was that I was her Saturday morning alarm clock. And she took so long to open the door because she went to the bathroom first. I always hoped she washed her hands.
I delivered the Daily News to a bar on the corner of 43rd Street and Wolcott. When the bartender paid for the subscription, he would tip me fifty cents and tell me to take a bag of Mrs. Vitner’s potato chips, any candy bar of my choice, and a pack of gum. One customer I never saw. She left me a note on her door in the rear hallway saying she would leave the money hidden in a crack in the wall. I was pleased by this arrangement because this mystery woman tipped well.
One little old Polish lady always wanted me to deliver both the Zgoda and Chicagowski directly into her hands. So I had to get off my bike, go knock on her door, she would say something in Polish that I didn’t understand, I would say I was the paperboy, and then she would open up the door. I did this everyday! Actually, I didn’t mind doing it, either. Of course, she wasn’t a big tipper, either, even though she considered herself extremely generous. On the day I had to collect the money for the subscription, she would tell me to enter her apartment and lock the door behind me. She would give a crisp brand new dollar bill to pay for her bill of 99 cents. I would then give her her change of one cent, which she would give back to me immediately as my tip and insist that I put the penny in a different pocket because that penny was for me and not the newpaper agency. Most subscribers would tip a nickel or a dime and that was extremely generous in all reality. But I really loved going through this weekly ritual for my one cent tip! Sometimes I had to run out of the apartment so she wouldn’t hear me when I couldn’t contain my laughter anymore. I really loved this little old Polish lady!
There was another little old Polish lady on paper route who received the Chicago Daily News, the Zgoda, and the Chicagowski. Her bill was about $1.50 per week. She wasn’t as demanding about her delivery, either. When I went to collect the money for her subscription, she would tip me 100%. I told her that $1.50 was way too much money for the tip, but she insisted. Well, being the polite Mexican boy that I was, I would pocket the money, in a different pocket, of course, so the Mr. Pressman wouldn’t get my tip. Sometimes, she would feel really guilty about the tip and slip me an extra nickel or dime before I walked out!