Criminal logo

The Man In the Pinstriped Suit

And other games of chance

By Craig HesterPublished 5 years ago 8 min read

He wore an ill-fitting, brown pinstripe suit and careworn wingtip shoes. The pit stains of his threadbare Oxford were permanent, even past the miracle of bleach, which would have surely disintegrated the shirt if used undiluted. He kept his hair glued to his head beneath a dark, twelve-year-old fedora. His ears stuck out just a bit too much, like handles on a three-quart pot, and his teeth were yellow from lack of any real regimented care.

Despite all this, upon initial inspection, he would appear to be a respectable businessman. And that is all any pickpocket needs – to pass an initial inspection. He wasn’t looking for long-term relationships. He just needed to be barely seen, deemed trustworthy and then forgotten after the encounter.

Lunch hour brought much of the downtown crowd out onto the sidewalks where he idled, scanning for his next mark. The street vendors were busy serving up hot dogs, hamburgers and the like as they would do every single day a throng justified their existence. He was hungry and thirsty but decided both could wait. These were rich hunting grounds, and his snares hadn’t been that worthy of the trophy room recently.

Then he spotted him: A middle-aged something or other of import. He would know what the guy did (at least usually) after getting a hold of his wallet. This one had clearly lost significant weight in recent memory. His suit hung on him as if he were a hanger. Perfect.

The finger-smith stepped out from the alcove he had been haunting and headed straight for his mark. Of course, the casual observer would never be able to tell this was his goal. He weaved in and out, keeping a keen eye, while not looking like he was keeping a keen eye. They were feet apart. Then it happened – the “bump and grab” like his father had taught his older brother and his brother had in turn taught him.

But this time he was thrown off just a bit. It was nothing he couldn’t compensate for on the fly. It was only that something else resided in the breast pocket of the thin man. The pickpocket decided to pull both, which made the encounter last just a few seconds more than it should and allowed the mark to register his face more than he preferred. Apologies followed. The victim was none the wiser and the pickpocket was on his way down the street.

The thief meandered a bit more downtown, glanced up at the incomplete Gateway Arch project and shook his head. He had to admit that even unfinished it was an amazing structure, though he really failed to see the point of it. He made his way back to his car – a 1955 Bel Air in similar condition to the rest of his countenance.

He slipped behind the wheel and pulled the two items from his own breast pocket. One was a weathered wallet. He pulled the cash from the fold and found a $20 bill. Not a bad haul. It would get him through the next couple of days. The rest of the material was standard fair – a driver’s license, misc. photos, a library card, etc.

The other item was a bit more interesting. He had lifted what could only be described as “a little black book”. It was leather bound and clearly expensive. The owner would for sure miss this more than the wallet or its contents. The pickpocket flipped it open and found rows of names, dates and descriptions all written in a tight, neat handwriting.

“J. Waller – Friday, May 1, 8 am – follow up on broken arm”

“M. Wilson – Monday, May 4, 10 am – mole removal.”

The list went on for pages like this. He must have been a doctor, despite the legible handwriting.

The pickpocket continued flipping through the book and a slip of paper fell out and landed unceremoniously on his lap. A chronic gambler, he instantly recognized it as a lotto ticket. “Hmmm,” he thought, “maybe there is even more value here than I realized.”

He looked at the timestamp on the ticket and noted the first chance anyone would have to know if this were a winner would be the afternoon paper, which was due to be on the street soon. He got out of his car and glanced around at the rusting newspaper vending machines on the street -- all empty.

Thirst was eclipsing curiosity at this point and he knew the odds of this being a winning ticket were extraordinarily slim. He cranked up his jalopy, sent up a plume of carbon dioxide and headed out of town. He needed a bar where he could clear his head, get a drink and figure out where to stay for the night.

Just as urban was giving way to rural, the pickpocket found the kind of place he was looking for to get a second wind -- “The Lucky Strike.” Not a bowling alley, as the name would imply, but a pool hall with a traditional bar. Well, just barely a pool hall with only four tables, all with felt looking one game away from becoming completely unraveled.

As he walked in he realized the entire place was one “lucky strike” away from falling apart. The cracked and faded leather bar stools, warped hardwood floors and broken mirror behind the bar could, no doubt, tell countless stories.

The place sat nearly empty with only two people at the bar, the tender behind it and two older fellas playing dominoes at the table nearest the door. The pickpocket went up to the bar and ordered a beer with his most recent score. He was just about to pull out the little black book to look and see if there was anything else of value. He had it clear of his pocket when his heart came to a screeching halt for a good five seconds.

This couldn’t be possible, he told himself. And yet, there was no mistaking the sagging suit of the doctor two bar stools down. He wasn’t sure what to do. If he just bolted that could look suspicious. He could try to avoid eye contact. What to do? Instinct of the trade finally sunk it. Order your beer, drink it and then leave casually. There is no reason to think he would recognize you if you just stay cool, he thought, almost at a whisper to himself.

The man next to him was a good 75 pounds overweight and the bar stool groaned as he shifted on its axis. This is what made what happened next such a shock to the pickpocket. He would never have suspected that a man of his girth could move so fast. But in an instant, he was off the bar stool, leaned down to the floor and then popped back up.

“Look what I found!” Everyone snapped out of their reverie and looked at the man.

“A lotto ticket!”

The man in the pinstriped suit froze. If someone struck him at that moment he would have surely shattered. What immediately followed wasn’t planned but unfolded with lightning speed.

The pickpocket reached up and snatched the ticket out of the overweight man’s hand and matter-of-factly stated, “that’s mine.”

Within seconds of doing so he was staring down the barrel of a Westley Richards and Company twelve gauge that was clearly in its second century of use.

“Mister, I don’t know you. But I’ve known Ralph here for 20 years. If he says he found that ticket, then that’s damn well what happened. Unless you got proof that is yours you better hand it back.”

From frozen to fast talking in forty five flat, the pickpocket called on one of his other talents – persuasion. Knowing full well that ticket was most likely worthless, he still wasn’t going to just give it up. Too bad he hadn’t memorized the numbers.

“I understand your position,” he said more coolly than anyone could have anticipated.

“But that is indeed my ticket,” he stated.

By that point, the entire population of the bar, as small as it was, stood in rapt attention to see where this was headed. The finger-smith stole a glance at the doctor to see if he had been recognized and it didn’t seem to be the case.

“And as I don’t have an afternoon paper, I have no idea if it has any value,” he went on. “Now you aren’t going to let me walk out of here with this. That’s obvious. But I also know it doesn’t belong to this gentleman here. I dropped it on the floor and he picked it up.”

Everyone listened without interruption.

The phrase “winging it” was coined for what the pickpocket was doing right then. But, in truth, the whole thing was barely underway before he knew exactly what he was going to do. He was good at a few things in life beyond being a quick-witted thief. And one of those was hustling pool.

It was his least favorite way to make a living. You had to spend a lot more time with the mark and as they realized they had been hustled, they would get increasingly cranky. Often you end up with no money, or worse, a bloody nose. But today it was his only obvious refuge.

Then it came.

“You know, I had a lotto ticket too,” the doctor said. “I thought it was stolen earlier today, but maybe that is mine and I dropped it here yesterday. Too bad I didn’t memorize the numbers.”

Still no look of recognition.

The thief loved it when people did what they were supposed to do right on cue.

“Well then, that makes my proposal even more appropriate,” the pickpocket said. “We have three people laying claim to this ticket. I propose that we split into two teams of two and play a game of pool for it.”

Even the fellas playing dominoes had stopped their match to pay closer attention.

“We agree to do this before we look up whether it is a winner. My suggestion is that the bartender and I here make one team and, Ralph, was it? Ralph joins the other claimant.”

The pickpocket let the ensuing silence grow louder. The tension slowly left the room. The bartender lowered the shotgun but kept it handy. There was murmuring and then agreement.

The bartender came around and took the ticket from the thief. He didn’t protest.

“Okay, Joe and Andy here playing dominoes are going to watch this ticket.” The bartender pulled out a pocket knife and then stabbed the ticket right into the table between the two men.

“Ralph, if you will reach around the bar there, you’ll find the evening paper.”

Ralph riffled through the pages.

“Okay, the lotto is twenty grand right now,” Ralph let out a sharp whistle. “The numbers are 56-72-18-13 and 12.”

All the color drained from the bartender’s face. The numbers were an exact match.

With palpable tension, the match managed to go off with little fanfare or conversation until the pickpocket found his moment. Keeping his back to the door, he sent the cue ball sailing off the felt right into two of their beers on an adjacent table. It shattered one of the glasses, knocked another to the floor and caused everyone to look that way.

In that instant, the thief turned, headed to the domino table, pulled out the knife, snatched up the paper underneath and sprinted to his car.

He was about a mile away when he looked down to see he was holding a scrap of paper with the initials “J and A” at the top and domino scores on both sides.

fiction

About the Creator

Craig Hester

Being a husband and father come first. Then I make my living in the watch business to provide for them. Writing is a sideline passion since youth. Hope you enjoy my musings.

Reader insights

Be the first to share your insights about this piece.

How does it work?

Add your insights

Comments

There are no comments for this story

Be the first to respond and start the conversation.

Sign in to comment

    Find us on social media

    Miscellaneous links

    • Explore
    • Contact
    • Privacy Policy
    • Terms of Use
    • Support

    © 2026 Creatd, Inc. All Rights Reserved.