How to Be the Worst Paperboy

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Like this. Only in color. And with a stolen scooter. And macking on the neighborhood chicks.
Like this. Only in color. And with a stolen scooter. And macking on the neighborhood chicks.

I grew up poor.

In a Catholic school with uniforms and predominantly wealthy classmates.

We weren’t, like, destitute. The lights and hot water always worked, and there was always food in the refrigerator, so I don’t want to insult people who truly know poverty.

But, relative to my life experience and most of the people I know, I was poor.

Free lunches at school. Low-income neighborhood. That sort of thing.

We all wore Navy-blue pants. Every day. Had to.

The only way we could express ourselves was to wear cool sneakers, though I used to call them tennis shoes despite never playing tennis once in my entire life.

I grew up in an awesome era of sneaker design. Air Jordans were the Holy Grail.

I never had any.

Best. Shoe. Ever.
Best. Shoe. Ever.

But there were shoes worn by other great athletes, too. Bo Jackson. David Robinson. Dominique Wilkins. Ken Griffey, Jr. Charles Barkley.

These shoes ranged from $75-$130 in late 1980s’, early 1990s’ dollars.

My parents couldn’t afford them.

“Mom, I at least need Nike Air or Reebok Pumps. I can’t go to school in crappy Jordache and L.A. Gear. Honestly. I’ll get made fun of.”

“You’ll wear Jordache, and you’ll like it! No one can tell the difference anyway!” she said.

But everyone could tell the difference. We were sneaker experts at that age.

Eventually, the money situation loosened up and I got to wear relatively cool shoes.

But between my Poor and Just Kind-of Poor stages, I had a paper route to help supplement my vanity.

The Paper Route

I don’t even remember how it began. But begin, it did.

One day, the papers started showing up on my front porch. Huge piles of free weekly newspapers strapped together, with a ton of little plastic bags.

One night per week, I would have to cut the straps off these huge newspaper piles, roll up several dozen, and individually stuff them into the plastic bags.

I got pretty good at it. If they were the right size—not too thin, and not too thick—I could do it rather quickly.

Roll, stuff. Roll, stuff. Roll, stuff. Over and over and over again.

I would then stuff those individually wrapped newspapers into brown grocery bags.

If the papers had a thick insert—like you see in the Sunday paper—this process was BRUTAL. Took forever, didn’t fit in the bags, and was extraordinarily heavy on my young shoulders while carrying them on my route.

I had three streets to cover.

I became a crack shot tossing newspapers. If I wanted to hit the welcome mat, I could do it.

If I wanted it on their steps, I could do it.

If I wanted it in their bushes, I could do it.

I don’t think anyone read this paper. It was little. It was free. And people didn’t care. In fact, people would yell at me sometimes for putting an unwanted newspaper on their porch. They didn’t care that I was a little kid.

I guess I was spamming before spamming was cool.

I wish I could remember what I thought about walking up and down those streets week after week. Just 11 or 12 years old. Delivering unwanted newspapers to the same people I bilked for extra baseball card money running my school candy-sales scam.

A miscreant.

Testing my moral limits. Pushing my moral boundaries.

Walking up and down those streets grew tiring. So, I started to find shortcuts. And take them.

I’d deliver to every door. Some houses had more than one door on their porch, but weren’t necessarily a duplex. Some houses had visible side doors. If I saw a door, I’d throw a paper in front of it. I was in a hurry. I had little-kid shit to do.

I’d steal scooters. I only did this once. And yes, I feel bad about it. I took some kid’s scooter. It was just laying out in the grass. I grabbed it, went super-fast through my paper route, and left it in someone else’s yard at the end. Like a car-theft joyride.

I’d stop and flirt with cute girls I knew from school or from the public school. One of them was really cute and I kind of had a crush on her. She was a year or so younger than me. I’d just stand on her porch and talk to her for 15-20 minutes sometimes. She transferred to our school when I was in junior high, and when I was in 8th grade she wrote me a poem telling me how much she liked me. That took guts. And instead of being flattered and respecting her privacy, I showed a bunch of my friends to look cool and acted like I didn’t like her.

“You’re walking on air. I’m walking on steam. Together, we’d make a great team.” That was one of the lines in her poem we used to snicker about every time we’d see her in the halls. Dick move.

I’d pit stop at my stepdad’s brother’s place which was on my route and play Nintendo for an hour with my cousins. I was older than them, so I was always showing off my video-game chops. How to beat Super Mario Bros. with one guy. The best weapons to use to quickly beat Mega Man 2. Where the secret caves and staircases were hiding in The Legend of Zelda. To make up the time I was spending playing video games, I had to do something about all those pesky newspapers that weren’t delivering themselves.

I started throwing them away. A few in a trash can here. A few in a trash can there. Until I started just dumping the entire load into local businesses’ dumpsters behind their buildings. Then, I’d go hang out with friends, or I’d go flirt with girls, or I’d go play video games with my cousins to hide the truth from my parents.

I grew up in a small town. Just over 20,000 people. So, I should have thought through the possibility of one of my parents driving by my paper route once in a while.

One day, not 10 minutes after leaving the house with a couple hundred newspapers, my stepdad drove by me walking down the sidewalk—with no papers in my paper bag.

Oh. Shit.

He was pissed.

Made me crawl into the dumpster and fish out all the papers and then go deliver them.

I probably got my ass beat a little when we got home. And I probably deserved it.

My parents couldn’t believe it.

“But they’re free!!!” I protested. “No one reads them anyway!!!”

And that’s when my stepdad explained to me the concept of the newspaper advertising and how all of those companies had paid money to the newspaper to have readers see the ads—the driving force behind that news getting written and the employment of a group of people with families. A business model that was ironically responsible for every paycheck I received between 1998 and 2009 during my newspaper reporting career.

I had to write a mea culpa letter to the newspaper.

They graciously let me keep my paper route, accepting my apology and my promise to do better.

And I did.

I probably still flirted with the girls.

I probably still delivered papers to every possible door.

I probably still pit stopped for a quick video game session every now and then.

But that was the last time I ever stole anything.

My career as a thief, short-lived.

And thank God for that.

I wasn’t very good at it anyway.

15 thoughts on “How to Be the Worst Paperboy”

  1. I grew up in a similar state of poor. I wore hand me downs and thrift shop clothes and yes everybody knew. I worked on our farm no opportunity to work away from home until I was 15. Man that first summer job paycheck was incredible!

    Awesome story Matt thanks for sharing 🙂

      1. Nope, about the same except there weren’t any cute boys to flirt with or video games, we had a swimming pool though and a dog which I got distracted with all the time! I did a lot of the ‘women’s’ work keeping house and preparing meals as well. I would dance in the lounge when I was meant to be vacuuming or peeling potatoes. Sometimes dinner was quite late. Sometimes I would wander off and lose track of time and I would steal money when I was in charge of the cash box for the gate sales. But I never got caught. I knew it was wrong and quietly made my own amends.

        The worst time I think was Christmas, our busiest time of year (we grew berry fruit and had large hothouses of tomatoes etc and mandarin orchards) we would work like crazy leading up to it so that we could have part of the day off. Christmas morning often wouldn’t start until 11am because everyone was too busy sleeping. Most years the berry picker would come in the night and we would be getting up at 2am or whatever time they were coming to grade berries on the machine under lights. No wonder I am a night owl.

    1. I could! But then I’d just be running around dunking on people all the time and making people feel bad. Which is not what I want to do.

      Yeah, I have no idea how that popped into my head about the girl. She was very cute. And we used to chat on her porch. Then a couple years later she wrote me a poem. And I was a dick about it.

      Bad form. I’m not proud. I promise.

  2. I had more time today, so I read up on more of your posts. This is probably my favorite. I think it helps that we’re the same age. I had L.A. gear Regulators, and a pair of Andre Agassis… because apparently I was obsessed with anything neon.

    Keep posting, I’m a big fan.

  3. I had a paper route, too, around that age. I got so sick of those ‘circulars’ (the advertisement inserts) I disposed of them …. down the sewer. Oops. Not only did I get busted, I had to go fish out many a soggy glob of pulp from those catch basins. Ahhh .. all memories now. Nice post, great blog!

  4. This is a cool story, fun to read. Sounds like a great script for an episode in a coming of age sitcom like ‘The Goldbergs’…which is totally rad, btw

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Matt Fray

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