The Chicago Paperboy

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Status: Finished  |  Genre: Thrillers  |  House: Booksie Classic

Eighteen year old paperboy Charlie Montgomery gets a job promotion and begins delivering papers in a rich Chicago neighborhood, where he meets the love of his life, and the story goes on from there.

Chapter 1 (v.1) - The Chicago Paperboy

Submitted: April 12, 2013

Reads: 144

Comments: 2

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Submitted: April 12, 2013




"Get your papers! Big headlines today!"

Eighteen year old Charlie Montgomery stood on the street corner hard at work at his part time job: selling newspapers. The tall and black haired young boy worked two jobs to help support his medium sized family of four. Three days a week, Tuesday, Thursday, and Saturday, he stood on the busy Chicago, Illinois street corner selling papers. On Mondays, Wednesdays, and Fridays, Charlie worked in the Smith Pencil Factory where he ran the wood cutting machine. With the help of the money that Charlie himself earned from his two jobs added to the pay that his mother, brothers, and sister brought home, the family had just enough to get by.

The Montgomery family was not the richest in the Illinois city, nor were they the poorest; they were somewhat in between. The high classed and sophisticated of the city looked down on people of the Montgomery family's kind, and the poor looked up to them for help moneywise.

Charlie's father, Daniel, had been killed in a terrible house fire when Charlie was only three years of age. The Montgomery family had suffered a loss of two during that tragedy, not only Daniel, but a newborn daughter, Catherine. The other members of the family had barely escaped. Henry, who was only seven at the time of the fire, smelt the smoke early in the morning, and despite his young age, knew exactly what was going on. Bravely, he awoke his younger brothers, Jack and Charlie, and they made their way to wake their parents. Claudia Montgomery, who soon was going to have a baby, was told by her husband to take the boys outside, and that he himself would get Catherine and follow shortly. Claudia did as she was told, but after a long time of waiting in the hot, dark, and sticky July summer morn, knew something was wrong after not seeing her beloved husband and baby daughter exit the burning house. Daniel and Catherine Montgomery were gone, to be seen no more 'till the family was reunited in Heaven.

Claudia took the boys and they moved to a run down apartment building in the heart of town, and there they tried to rebuild their lives. Never remarrying, Claudia raised her children alone, schooling them the basics of mathematics, reading, spelling, writing, and superiorly, above all, teaching them the Bible. From the story of Noah's Ark to the Good Samaritan, she wrote out quizzes for her children to take, then, once completed, graded them, always finding the result that her children had mastered the Subject.

The Montgomery family grew to be close-knit, promising to always stick together through thick and through thin, helping those less fortunate along the way, doing good duties, and spreading the News.

I hope you will enjoy my book,and have fun reading it. -G.A.W.

Cast of characters in the Montgomery family: Claudia, the mother, and the children, Henry, Jack, Charlie, and Elaina


Chapter One: A Step Up Into Society

"Charlie! Charlie!"

Jimmy Dylan came running up to Charlie who was standing on the street corner. 

Charlie, startled by the suddenness of Jimmy's arrival, turned around and asked his business companion, "What is it, Jimmy? You got me there for a minute, running up to me like something was wrong."

"There's nothing wrong," Jimmy answered enthusiastically. "In fact, everything's right! The boss told me to come and get you to take you back to the office. He's got some great news for the both of us!"

Charlie smiled. Great news was exactly what he needed. He stood there wondering what it could be. Time after time had received bad news, about his job, his family, his surroundings, his everything. Not often did he hear good news, so that made this moment a special one.

"Well, come on, then!" Jimmy exclaimed. He grabbed Charlie's arm and began to pull him along, and Charlie had no choice but to follow. 

Jimmy was a quite energetic thirteen year old boy who took up the job of selling newspapers as did his friend, Charlie. He had red hair and green eyes, and his parents had emigrated from Northern Ireland. Jimmy spent most of his free time roaming the streets of Chicago with a group of boys from his neighborhood. That was what he did until he became a paperboy: playing marbles and jacks in the alleyways, mistakenly noted for the 'trouble rouser' kind.

When the two boys walked inside the office, they rushed to the boss' desk.

"Mr. Lowry," Jimmy said, out of breath, "and I brought Charlie with me."

Mr. Lowry sat up from his reclined position in his swivel chair. "Yes, Jimmy." He rummaged through a pile of papers on his desk, pulling out bills, letters, papers, calendars from years past, until he found what he was looking for. He scanned the thin sheet of notebook paper, then said to the two boys standing before him, "Jimmy, Charlie, you two have now been assigned to deliver papers to the suburb of Niles in the south eastern part of the city."

Immediately, Charlie knew what Mr. Lowry meant. Niles was one of the richest suburbs in the city of Chicago, and neither he nor Jimmy ever dreamed of going there. Without thinking, Charlie yelled, "Whoopee!" and his stack of undelivered papers flew into the air. As soon as he realized what he had done, he apologized to Mr. Lowry, who only laughed.

"I'm sorry, Mr. Lowry," Charlie said nervously as he began to pick up the papers that had fallen 'round him.

"I understand your enthusiasm, Charlie," replied the boss. "If I were in your place I would probably have done the same thing."

"Thanks," Charlie replied.

Jimmy thought of a very important question. "Mr. Lowry," he asked, "when do we start delivering to Niles?"

Mr. Lowry answered after clearing his desk, "Tomorrow morning."

"That soon?" Jimmy asked excitedly.

"Yes," Mr. Lowry answered. "And I expect you two to be on your best behavior. No fooling around or pranks, nothing to make a bad impression on you, your families, or the paper office."

"Yes, sir!" Jimmy answered, standing staunchly and saluting his boss.

Charlie, who had just finished clearing his papers, also said the same.


"I can't believe it! Ma, can you? How about you, Henry? What about you, Jack? Can you believe it, Elaina? I'm going to Niles!"

At dinner, Charlie informed his family of his new paper route.

"It is sort of unbelievable for someone in the family," Elaina said after clearing her plate of mashed potatoes and peas.

"I think it's great," Jack said.

 "So do I," added Henry. 

After not hearing a comment from his mother, Charlie asked her, "Ma, what do you think about my going to Niles?"

Claudia looked up and answered her youngest son. "I think it's just wonderful, Charlie. I think it's just wonderful."

"Thanks, ma," Charlie replied. 


Once through with dinner, Charlie brought in the washtub and got a bar of lye soap from the cabinets. He planned to take a bath before he went to bed so that he could make a somewhat decent appearance when he went to Niles. He was very excited about his journey the next day, and of course, he wanted everything to be perfect. After his bath, Charlie made sure he brushed his teeth and cleaned his ears, the two things he managed to 'forget' every time he took a bath. Charlie finished with his bath, then kneeled by his bed and said his prayers.'

"Dear Lord, thank You for everything You've done for me and my family. Please be with us in the future as you have in the past, and please, Lord, please be with me when I go to Niles tomorrow. In Jesus' name, Amen." Charlie opened his eyes, assured that God would take care of his needs. With that, he crawled into bed and drifted off to sleep, anxious for the morning to come.


Rather than Charlie, Elaina was the first to wake the following morning. She checked the time on the old pocket watch that hung over the doorway, and the time was seven in the morning. Immediately she realized that her brother wasn't awake, knowing that if he didn't reach the newspaper office by seven thirty that he would be too late. Elaina hurried to the Murphy bed where Charlie slept and shook him gently. "Charlie," she said, "it's time to get up. You don't want to be late for your job."

Charlie opened his eyes quickly at the thought of what his sister just said. He jumped out of the bed and scurried to the dresser that he and his siblings shared and pulled out his best sweater and pair of trousers. Snatching a striped red and green tie down from the coat rack, he pulled the privacy curtain to and changed clothes. Charlie then rushed to find his newly sewn pair of black woolen socks and his freshly shined shoes to put them on. And finally, as he rushed to the kitchen, grabbed his hat from the couch post.

Claudia had just woken up as Charlie hurriedly searched for something to eat. "Charlie," she said, "why the rush? Sit down and I'll fix you some eggs and toast."

"I can't, ma," replied Charlie, who had just found two pieces of day old bread in the bread box. "Look at the time." He pointed to the pocket watch, which now said seven-fifteen. "I've got to be at the office by seven thirty, so I've got to hurry. By the way, these two pieces of bread will hold me over for now." He swallowed a mouthful and added, "I'll see you later. Bye!" He ran out the door, which slammed behind him.

Charlie ran as fast as he could down the busy Chicago street, and as he rushed at top speed through the office door was relieved at the sight of the clock. Seven twenty-five. Charlie sighed as he leaned against the wall. He surely was out of breath after the long run, but he couldn't wait to go to Niles. Jimmy Dylan would be going along with him, along with another boy, fifteen year old James Hankey.

Charlie walked to the boss' desk where Jimmy and James were, and where Mr. Lowry was directing them to go in Niles. When Mr. Lowry saw Charlie, he said to him, "Hi, Charlie. In Niles you're to go the area of Waukegan Road and deliver papers there. When you're done, simply come back here, and don't linger around there. We don't want anyone getting suspicious."

"Yes, Mr. Lowry," Charlie replied. He took the stack of papers that his boss had set on the desktop, and found that they were labeled with his name, the streets he was supposed to deliver to, and Niles. Charlie was proud that he could now say he had taken a step up into society, and now, yes, now, could he have the feeling that he would somehow get his family out of poverty.








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