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[Short Story] Jillian the Gumshoe

In honor of my roving store venturing forth into the ether I present a free story for anybody who manages to stumble onto my plateau. Enjoy!




Jillian the Gumshoe


Jillian Trachtenberg is a typical fourteen year old girl. She goes to school, hangs out with her friends and enjoys working the occasional case to help local law enforcement solve a crime. Okay, okay, so she is more a-typical of teens her age, but the other kids would do it too, if they were capable. Regarded as a prodigy in her middle school she is allowed to attend the high school for certain classes which gives her a lot of unsupervised time to herself. When she’s not in class, probably ditching, she is usually sitting cross-legged under a tree diligently taking notes in her black and white notebook. Jillian keeps to herself most of the time unless she is hanging out with her best friends, Bernard and Courtney.

Jillian is so focused on taking notes about a potential future case she doesn’t even notice the football currently flying at her face.

WHAM! The ball hits her between the eyes, “Ow!” Jillian cries out, rubbing her forehead.

“Sorry, Jill!” Bernard, runs up, “I said ‘heads-up’. I thought you were paying attention.”

“But I was looking down,” Jill says, handing his ball back to him.

“You okay?” Courtney jogs up, “That looked like it hurt.”

“Only a little,” Jillian gets up and starts to leave, “I gotta go anyway, my mom said she needed me to come home a bit earlier today.”

“Alright,” Bernard says, “Sorry I hit you in the face.”

“Don’t worry about it, I’ll get you back!” Jill jokes and waves to them as she walks off the field, “Bye!”

“Bye!” Courtney waves, then Courtney snatches the football from Bernard to make him chase her.


Jillian and her friends play at a big, local football field open to the public on the weekends which sits at the end of the long main road that housed the majority of the businesses running through the heart of their small town of Pipaskua, South Dakota.

Jillian always enjoys taking a stroll through her home town, going down the main street always felt warm and comfortable to her. Shop owners setting up their stores and greeting customers as they pass, the smell of freshly baked bread wafting from the bakery on the corner of the T-junction in the center of town, jovial and upbeat music emanating from the most popular outdoor eatery in town, friendly faces everwhere, nice weather and a tight-knit community all led Jillian to believe that her town just might be the best town on earth. So, she made it her duty to protect it and that is why she decided to do her best to collect as much information to help prevent any crimes that may occur, or solve the ones that do. She has taken a lot of notes on just about anything throughout her town, mostly independent work so far, but Jillian hopes to truly assist in real case someday. Finally, that opportunity arises…

Jillian makes her way down Main Street, leaving Zerini Field, rubbing her forehead, when the local produce owner comes running by, almost knocking Jillian on her butt!

“Excuse me!” Jillian calls out to him, but the man doesn’t hear her and continues to sprint down the street, “That’s strange, I wonder where Mr. Hillibrand is going in such a hurry.”

Jillian continues walking until she finds Mr. Hillibrand standing outside of his local produce market in front of a small box sitting on the ground outside his store with a few people gathered around it. Jillian inspects what all the ruckus is about, poking her head between the small crowd to take a look at the box. The semi-circle of people stand around the wood box sitting upside down on the ground, seemingly nothing unique or special about it. Just then a police car pulls up and two officers get out.

“Alright, folks, let’s disperse,” Officer Oenesco waves his hands to break up the crowd, “Nothing to see here.”

“That’s right there’s nothin’!” old Mr. Hillibrand shouts, “Bertha has been stolen right off this here box!”

“I’m sorry, sir, Bertha?” Officer Oenesco asks.

This is when Jillian butts in, “Bertha is Mr. Hillibrand’s prize watermelon.”

Officer Martin’s face contorts, “Prize watermelon?”

“Mr. Hillibrand won first place for the biggest watermelon in the region during the Harvest Festival, Officer,” Jillian informs them.

“Yes, exactly!” Mr. Hillibrand confirms, “Thank you, Jillian! Will you be able to get my melon back before anything awful happens to it?”

“Like what, they’ll eat it?” Officer Martin says facetiously.

Officer Oenesco chuckles, “We’ll do our best, Mr. Hillibrand.”

“Bah!” Mr. Hillibrand waves them off as the Officers leave and the crowd disperses. Jillian follows Mr. Hillibrand into his shop.

“I’m sorry to hear about Bertha,” Jillian says sincerely.

“Would you look for it, Jillian?” Mr. Hillibrand asks, “To be honest, I trust you more than the boys in blue, and I’d bet know this town better than them.”

“I’m on the case, Mr. Hillibrand!” Jillian gives him a thumbs up, and with that Jillian races out of his store, leaving Mr. Hillibrand feeling better already.

After Jillian leaves the store she takes out her notebook and reviews her notes:

Mr. Jason Hillibrand, sixty-seven years old, friendly widower, wife’s name was Gertrude.

Owner of local supermarket simply called “SUPERMARKET”, sells fresh produce and other groceries. Drives a navy blue Ford pick-up truck.

Won first prize for largest watermelon in Harvest Festival 2020. Watermelon named ‘Bertha’.

Won first prize for largest pumpkin in Harvest Festival 2010. Pumpkin named ‘Hampton’.

Owns two parakeets, Samson & Delilah, unsure of coloring for either.

Interests include: visiting Gertrude, managing store, birds and growing food.


Jillian ponders over the few facts she had about the case as she walked. Who would steal a giant watermelon? Why would someone want or need one? Perhaps an angry contestant didn’t like the results at the fair? Was it about the melon at all, or was it to spite Mr. Hillibrand? Maybe a jealous, old lover of Gertrude’s? Jillian thinks without any strong ideas all the way until she arrives home.

Upon entering, her mother breaks her concentration, “Hello, dear! How are you?”

“Uh, good, Mom,” Jillian responds, half-aware of her mom or what she said, then she goes into her room and closes the door. After a few seconds Jillian comes back out with sheepish look on her face, “I’m sorry, Mom, I was thinking. Bertha was stolen and Mr. Hillibrand put me on the case!”

“Is that so?” Her mom replies, “Any hot leads?” she says, giggling.

“Mom,” Jillian whines, “This is serious.”

“I know,” her Mom says, innocently, “That’s why I find it so humorous. My little girl is turning into the detective your father always wanted you to be.”

“Mom…” Jillian starts to get annoyed.

“If I’m going to be letting you taking on cases while you should be doing your homework then you’re going to have to put up with my telling you how proud your father would have been of you,” her mom says with a big smile, knowing Jillian must comply. She kisses Jillian on the cheek, “Now, run along, solve your little mystery. And remember, no homicide cases, that’s the deal.”

“I know, I know,” Jillian groans as heads back into her room, “Nothing interesting.”

“Excuse me, what happened to ‘the thrill of the case’ is enough for me?” her mom reminds her.

Jill rolls her eyes, ignores her, and closes her door then gets to work.

After researching more about the Harvest Festival, its contestants, Mr. Hillibrand, his watermelon and watermelons in general, Jillian believes she has a lead.

First, she decides to visit the runner-up of the Harvest Festival prize and ask him a few questions. Thankfully, he happens to live on a farm close enough she could ride her bike to.

“And you weren’t jealous of Mr. Hillibrand for beating you?” Jill asks.

Mr. Hosea shakes his head, “No, I thought Bertha was more than deserving of the prize that year. In fact, I was surprised when Melvin requested a recount, I thought the decision was an obvious one.”

“You’re referring to Melvin Armstrong, one of the judges, correct?” Jillian flips a page in her notebook to confirm.

“Yes, Melvin seemed to be the only hold out,” Mr. Hosea shrugs, “But I guess he was overruled.”

“Thank you so much, Mr. Hosea,” Jillian shakes his head, “Have a good day.”

“Good bye, young lady.”


Jillian confronts Melvin Armstong inside his town hall at his job as comptroller for the town, “No, I don’t know anything about any watermelon, please leave.”

Melvin forces Jill off the premises and now, unsure of how to proceed she sits on the long steps outside town hall.

“Jillian!” she looks up to see Bernard tossing his football to himself as he walks up, “Long time no see.”

“Hey, Bernie,” Jillian smiles, “Where’s Court?”

“She had to go run some errands with her Mom,” Bernard tosses his ball in the air and catches it, “Watcha doing?”

Jillian announces proudly, “Mr. Hillibrand put me on my first real live case!”

“No way!” Bernard forgets trying to catch his ball, letting it fall to the ground and bounce into the grass haphazardly, instead he hurries to sit next to Jill and starts reading over her shoulder, she doesn’t seem to mind.

“Bertha was stolen and I’m starting to think Mr. Armstrong stole it,” Jillian says, thinking out loud.

“Why?” Bernard’s simplicity cuts to the heart of the matter.

Jillian is at a loss, “…that, I don’t know.”

“So, it might not have been him?” Bernard ask innocently.

“No, it might not,” Jillian groans, “But he’s my only lead.”

“What’re you gonna do next?” Bernard asks.

Jill smiles and shakes her head, looking at Bernard, “Thanks for keeping me on track.”

“Oh, uh,” Bernard smiles back, “You’re welcome.”

Just then Jill gets an idea, “Hey, you wanna help?”

“Yeah I do!” Bernard says, enthusiastically pumping his fist in the air.

“Great,” Jill replies, “Follow me”


Later in the day Mr. Armstrong is leaving work, he exits his office and is about to lock up when Bernard runs up to him, “Excuse me, Mister, I was wondering if you’d like to buy a candy bar to support our local football team?”

Mr. Armstrong stops and looks at him, seeing only the football in his hands, “Where is the candy, son?”

Bernard hadn’t thought out his lie but thinks fast, “Oh, uh, because I got tired of carrying it around since nobody is buying. It’s over there,” He points to a generic direction down the hall, “I’ll go get it if you want to buy some, did you want some?”

Mr. Armstrong tries to resume locking up, “No, thank you.”

“Wait, are you sure?” Bernard’s persistence stops him again and Mr. Armstrong turns to face him as he listens to Bernard politely, “We got milk chocolate, and dark chocolate and toffee and the kind with nuts, I think they’re almonds, and we got…”

While Bernard provides a distraction Jillian carefully and quietly sneaks behind Mr. Armstrong into his office.

Once inside the dark room Jillian starts to look for any indication that he may have taken the watermelon. She rustles through papers on his desk, rummages through his drawers, examines documents on top of and inside nearby cabinets but finds no clues. She is just about to give up and leave when she accidentally bumps the mouse of his computer on his desk which turns off the computer’s screen saver, lighting up the room forcing Jillian to quickly switch the monitor off before Mr. Armstrong could see.

Seeing the flash of light Mr. Armstong peers back into his room for a moment but sees nothing, then he shrugs, closes the door, and locks it while Bernard desperately attempts to get his attention.

Mr. Armstrong cuts him off, “Thank you, son, but no thank you. Now, I must be going.” Then he leaves Bernard standing next to the locked door, unsure of how to proceed.

Inside, Jillian gets up from behind the desk when she hears the door close and Mr. Armstrong’s shoes squeaking on the linoleum fade into the distance. She switches the monitor back on and sees on the desktop a file labeled “HARVEST FESTIVAL WINNER.pdf.” She double-clicks and it opens to find a picture of Mr. Armstrong and Mr. Hillibrand standing between the largest pumpkin Jillian ever knew was possible, standing more than two heads taller than both men.

Jillian prints the picture, restores everything to how it was and then exits the room to find Bernard sitting and waiting.

“Check it out,” Jill shows him the picture.

“Mr. Hillibrand and Mr. Armstrong are friends?!” Bernard asks.

“Seems so,” Jill states, “Thanks for the distraction, come on.”


Jill and Bernard find the same picture in a local newspaper printed at the time and shows it to Mr. Hillibrand.

“Ah, yes, I remember that Harvest Festival,” Mr. Hillibrand smiles reliving the memories, “You don’t think Melvin had anything to do with this, do you?”

“Why did Mr. Armstong want a recount when Bertha won?” Jill asks.

“Oh, because that old fool said Bertha wasn’t on a regulation mount,” Mr. Hillibrand waves it off, “He says that altered the scores in favor of my melon. He’d never do such a thing as this.”

“To be honest,” Jillian says sincerely, “I believe you.”

“Good,” Mr. Hillibrand says earnestly, “Melvin Armstrong is one of my closest friends and I know he’d never do such a thing.”

“Then we’re out of leads, right Jill?” Bernard says.

“Looks like my first case ever is gonna be a bust,” Jillian says with a distraught, forlorn sigh.

“Now, now,” Mr. Hillibrand shakes his head with disappointment, “Jillian isn’t going to give up so easily, is she? And on her first case too, tsk tsk tsk, I had such higher hopes for that little gumshoe and her notebook.”

Hearing his words gives Jillian determination and courage, “You’re right, Mr. Hillibrand, Jillian the gumshoe ain’t no quitter.”

“That’s right!” Bernard says excitedly.

“Now, that’s what I like to hear,” Mr. Hillibrand says with a smile, “I haven’t lost faith in you, dear, don’t lose faith in yourself. Now go on, find me my melon and solve your first case.”

“Thank you, Mr. Hillibrand,” Jillian says with newfound determination, “I will.”

Jill hurries out of the store followed closely by Bernard, “Where do you wanna go now?” he asks.

“I think I know who did it,” Jill says confidently.

“You figured it out from two seconds ago until now?” Bernard asks, confused.

“No,” she says, confusing him even more, “But I know how we can figure it out.”

“Oh,” Bernard says, not sure what she means but goes along anyway, “Okay, well, great. We should have done whatever it is sooner.”

“I didn’t think of it sooner,” Jillian admits.


Jillian and Bernard poke their heads up from behind a bunch of trash cans.

“Look,” Jillian points.

Following her finger he looks over to the docks to see a boat is just arriving and being tied off by a man in a black coat and a hat. A few sailors climb off and start to load large crates that are sitting on the dock onto the boat, the man with the black coat starts writing on a clipboard.

Jillian motions for Bernard to follow and they approach the man with the black coat, “Excuse me, Master Jackson?” Jill waves to him as they approach.

The man starts to light a pipe but looks up and smiles when he sees her coming, “Well, hello, little Jilly,” he lights and puffs his pipe, “How are ye this fine day?”

“I am well, thank you, how are you?” He nods in recognition then she motions to her friend, “This is my friend Bernard.”

“A friend of Jillian’s is a friend of mine,” Mr. Jackson smiles and nods at him, “How can I help the both of ye?”

“Have you heard or seen any very large shipments going out?” Jillian asks, “I’m thinking… very large wood box storing something delicate.”

“No, I’m sorry, young miss,” Mr. Jackson says, causing the children to turn away in disappointment, “Oh, wait, come to think of it we did have a large shipment scheduled, but it was cancelled last minute. It came from the large super market chain, the big one that got built recently, eh, what’s it called?”

“Green & Healthy,” Jillian informs him.

“Right, right, I’ve never actually been there,” Mr. Jackson admits.

“Me neither,” Bernard states flatly.

“It has nice air conditioning,” Jillian says, “Thank you for your help, Master Jackson.”

“If it was of help to you then I am glad, little Jilly,” Mr. Jackson tips his hat and the pair leave.

“How did that help?” Bernard asks.

“Now I know who did it,” Jillian says with a cocky smile.

Bernard stops in his tracks scratching his head, “You do? How?”


“Mr. Hosea?!” Bernard, Mr Hillibrand, Officer Oenesco and Officer Martin all cry out.

“You can’t think he stole the watermelon!” Mr. Hillibrand declares in disbelief, “Why would he? Him and I have no issue with each other.”

“No, you and he don’t,” Jillian confirms, “But Mr. Hosea and Mr. Armstrong hate each other’s guts.”

Mr. Hillibrand stops for a moment, “That’s true, ever since that darn pumpkin all those years ago!”

“Exactly,” Jillian says, nodding her head.

“Someone wanna fill us in?” Officer Oenesco asks helplessly.

Jill shows them the picture of Mr. Hillibrand and Mr. Armstrong standing on either side of their prize winning pumpkin, “This is the winner of the harvest festival ten years ago. The runner-up was Mr. Hosea,” Jillian continues to drop photo after photo of the next winners, “and every year since, Mr. Hosea has been the runner-up to Mr. Armstrong. I believe Mr. Hosea’s loss to Bertha was the last straw and he stole it out of his anger and jealously towards Mr. Armstrong. That’s why he was able to admit Bertha was better. Then he tried to ship the watermelon, had second thoughts and I think you’ll find a very large crate in Mr. Hosea’s barn.

Once confronted Mr. Hosea confesses to the whole thing and returns the prize watermelon, “Nobody cared when my second place squash was eaten by cats, so why should anybody care about his dumb old watermelon?”

“We don’t care about the watermelon or the first place prize, Mr. Hosea,” Jillian informs him, “We care about Mr. Hillibrand.”

The officers take Mr. Hosea away.

“Thank you for everything,” Mr. Hillibrand gives Jillian a big hug, “Now you really are Jillian the Gumshoe.”


Look for more kooky capers solved by the infamous Jillian the Gumshoe in more volumes of Menagerie Mysteries!


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