Submitted to: Contest #318

The Criminal Mastermind’s Mastermind

Written in response to: "Center your story around someone who’s secretly running the show."

Crime Fiction Funny

This story contains themes or mentions of physical violence, gore, or abuse.

I was venting to my therapist today, when he asked me a kind of personal question, “Do you enjoy your line of work?”

My Job..

Mhm..

I love it and hate it.

Honestly, I take genuine pride in my work. The issue is my boss.

His demands can kind of be too much sometimes. Just like last week, I sent him a simple email explaining how we are running low on funds and are going to have to find some way to make profits fast.

This guy almost tears down the door to my office as he storms in. He literally kicked it open, breaking the door frame, then slammed it shut behind him.

Seriously! Dramatic much? I mean, I guess that’s his whole shtick, but he could have at least knocked or something instead of scaring the hell out of me.

Then he goes hollering off at me, “What do you mean we are low on funds!”

Dude, come on. I thought I was clear in the email.

Regardless, I had to put on that friendly facade, I am a professional after all, “Sir, we’re basically broke.”

He started twirling around, pulling at the hair under that ridiculous hat of his, “Now that can’t be! Our last gig should have been enough to cover us for at least two months!”

Clearly he’s forgotten some major details, “Yes sir, it should have been. The issue is that we are still paying the henchmen that Daring Man apprehended from that last gig.”

He scoffs and jerks his head like I just said the most ridiculous thing ever. Then he continues on, mocking the concept, “Oh, so we provide workers comp now? Why are we paying henchmen to sit around in a jail cell?”

Honestly, I’m surprised I’m not numb to it at this point. Still, he wears his mask and I wear mine.

So I continue on with that cheerful but stoic persona of mine, “It’s to keep their mouths shut sir. They know where the lair is, and at least half of them have been to your housewarming party, so they also know your secret identity.”

Guy acts like a light bulb just turned on above his head. He went on in this giddy tone he gets whenever he is proud of himself, “I just finished this episode of my favorite show, and they had the exact same issue. We could just pay someone to kill them!”

I actually caught that episode he was talking about last night. Honestly it was pretty cool.

“Sir, I'd probably advise against that. If the other henchmen found out, they’re not going to want to work for you anymore. Also there is still the issue of funding. We don’t have money to hire hitmen right now.”

Here comes the part I really hate. I don’t know why in these circumstances do I ever expect anything different when he’s always going to say the same thing.

I swear to you he’s a cartoon character. Every time he gets red in the face, he starts breathing heavily, and acts like steam is shooting out of every orifice of his body.

The thing is about Mystro Sinclair, he hates resistance and not getting his way. I hear it from henchmen all the time. They’ll tell me how in the middle of a job, Daring Man swoops in, starts to foil Mystro’s plans, and the guy will begin to throw a tantrum about it.

Not surprising though considering this is the same guy who blew up the break room because we ran out of coffee pods.

This guy is a sore loser. He doesn’t even want to stand the idea of losing, before he can get out on the track. So with these tasks that seem impossible to achieve, and when I explain to him just how impossible to achieve they can be, he always has the same thing to say.

“Then get us some money, get us some hitmen, kill us some guys, and don’t let the henchmen find out! We are criminal masterminds here! Figure it out!”

The guy didn’t even give me a chance to speak. He just stormed off slamming the door behind him. Jerk.

We are criminal masterminds.

Sure. More like, Hey Shannon! I have a list of absurd things I want done, and I’m too lazy to think as to how to accomplish them. Here’s a pile of work stress to deal with.

At least it wasn’t as bad as the time when he wanted the lair filled with snakes, sharks and alligators.

Still, it’s the part of the job that I hate, but weirdly enough, it leads to the part that I genuinely enjoy. Which is getting this stuff done son.

First I had to look at what I was working with. Five guys in the penitentiary that needed to get iced. Fifteen guys ready to move in on a job, and barely enough money for next week’s pay period.

We got a van and a few guns. I thought maybe we could rob a bank, but I didn’t want any extra heat from Daring Man. Plus if the heist went south, which it did, we really didn’t have the resources to accommodate that.

So the best place to start was getting some resources. That’s why it’s always good to track the activities of other crime syndicates in Morgue County.

The Vipers were moving a shipment of arms and munitions down at the harbor last Tuesday. Easy pickings right?

Right. One issue though. The Vipers are one of the biggest factions in Morgue County, and I’d prefer not to start a war with them.

It’d be nice if they were at war with another faction though. Which they are. The Kingsnakes, a small sect of The Vipers that branched off to start their own dealings. The two sides have been at it for months now.

Now I could have started a line of communication with The Kingsnakes, but I’m pretty sure that would have gotten messy down the road.

Instead I had a better idea. A bit of a Boston tea party, a valentine’s day massacre idea if you will.

I got the henchmen to go to the harbor in Kingsnake’s attire; Black baseball caps with yellow shiesties. Now the biggest thing about this stunt was to have the element of surprise while also being seen.

I was honestly scared the whole plan was going to fall apart at this stage, but it’s always good to work with people you can trust.

The henchmen knocked out some guards, took their clothes, and made off with some guns, ammo and an armored ATV. All while setting off some fireworks off course.

Obviously The Vipers were pretty ticked. I don’t even think they cared to recover their stolen goods as they were too busy trying to get retribution from how The Kingsnakes embarrassed them. What made it even more funny, is that the Kingsnakes, being the blood thirsty little monsters they are, didn't even care to try and explain that they were being framed. They just went straight to shooting. A perfect diversion for Daring Man to deal with.

There was one issue though. The ATV. I honestly didn’t think the henchmen would be ballsy enough to steal one. They were so proud when they returned with it, boasting how it would be the perfect getaway vehicle for the bank job.

I was pretty ticked off. While they were celebrating at how cool they were, I was over there hoping that a giant armored vehicle didn’t raise any suspicions as it was driven around town, straight to our lair. Also I was trying to figure out just how we were going to sneak this thing across the city so we can use it for the bank job.

I worked pretty late that night, making phone calls, and cashing in favors. I was able to get some old colleagues on board, and I coordinated a plan to have the ATV towed by a semitruck discreetly around the city to a storage unit just down the street from the bank.

That raises another issue though; More accomplices, and more mouths to pay shut.

So came the time for the bank robbery. Now I would have considered this the magnus opus of the whole operation. I send in five muscles inside the bank, to act as crowd control, and to move the money for the look out team. The look out team keeps the outside just clear enough so there is still an escape route. They also help load the getaway vehicle. Everything was to be done in less than five minutes.

At least that is what was supposed to happen.

These absolute maniacs took the ATV on a joyride, crashed it into the building, then proceeded to turn the ceiling into Swiss cheese, and spent at least ten minutes just hanging out in the bank, terrorizing the poor folk.

Like come one, everyone knows banks are insured. Those check slotters wouldn’t even put up resistance if you came in with a water gun.

Thank the stars that Daring Man was busy dealing with that Vipers and Kingsnakes war I orchestrated. If not, that’d be more people behind bars I’d have to get rid of.

See, I think the henchmen got a little confused during the mission briefing. I told them, “And as you guys make your escape, cause as much chaos and havoc as you physically can without getting shot.”

They heard chaos and havoc and decided to treat the whole job like a rave. By the time the ATV was loaded, police barricades already surrounded the whole building.

Honestly, I think these maniacs did this on purpose so they could have more fun with the ATV, as they used this five thousand pounds of bullet proof military engineering to just blow through the barricades before doing donuts in the middle of the road and speeding off.

Crazy right?

I’m still surprised they were able to get away, even with the extra planning I did for their get away.

Not too far from the bank was a safehouse for the Vipers. Now you’d think, seeing a couple of crooks pulling in with a vehicle that was recently stolen from them, with a trail of police behind them, would cause some concern for The Vipers, right?

Nope, wrong. Remember those clothes the henchmen stole off the back of some poor unconscious Vipers? Well during the bank job, they disguised themselves in those outfits.

The Vipers are a big faction. So big in fact, that most of them don’t even know what operations are going on at any given moment. So when they saw what they presumed to be their own comrades coming in, all they knew what to do was help.

It was hilarious. I’m laughing under my breath now just thinking of it.

Man, I really wish I was there. To watch The Vipers transfer our money to one of their vans for us to ride off with. All while Daring Man finally makes it to the scene. Then to watch The Vipers hold Daring Man off, all while the henchmen make their final escape, and get away Scot free.

When I saw the henchmen knocking on my door, I almost exploded in excitement. Even with all the hiccups, I couldn’t have asked for better results.

Their little stunt increased the pressure on The Vipers and Kingsnakes from the authorities and Daring Man. With all that chaos, it leaves so much easy pickings for vultures like myself.

So I did it. I successfully coordinated an operation to keep me employed for another month, and to fix some other “issues” the syndicate is having.

Some real great inspiration from that T.V. show last night. I’m probably going to orchestrate a riot in the prison to take care of our little problem. We also got some extra money left over. Might just use it to shut some other mouths I dragged into this conspiracy, for good.

See that’s what I really love about this job, is to see everything play out. To have a plan for a sticky situation, and to see it through. I did that. Just like how I’m preparing a meeting for Mystro Sinclair to congratulate the henchmen on a job well done. Pretty sure he’s going to gawk around like he actually did something for once.

Which he did. Boasting the whole time like he was there every step of the way, leading the charge. Honestly in moments like this it’s quite entertaining to watch.

Though he’s a bit of a jerk and hot head, he’s got spunk.

Posted Sep 06, 2025
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