Infinite Jest: The Story of Jackie O’Rourke


Keeping his hands away from what wasn’t his had always been a problem for Jackie O’Rourke.

Jackie worked for Boss Harrigan, a shady Boston pol who had managed to amass a fortune in ways best contemplated in silence. Jackie was good at silence, and quickly became part of Harrigan’s inner circle. Liking the Boss’s flashy style, Jackie took to wearing fancy diamond cufflinks and an expensive pinky ring.

Whatever the Boss had, Jackie wanted, too. That included Harrigan’s wife, a tall, raven-haired beauty with a frosty attitude.

One night at the Boss’s brick mansion, the old man was holding forth about a new construction project in South Boston.

“Now listen to me, boys. I arranged for the contract to go to the Flaherty group. They’ll work hard, nights if they have to, and they’ll finish the job quickly, no questions asked. They’ll make money and so will we. Even better, we’ll make some new friends; it’s always good to have friends in the construction business. Remember that.”

Jackie’s attention had wandered when Harrigan’s wife entered the room. She gave Jackie a look that raised, among other things, his temperature.

“Hey, Jackie! Am I boring you?” thundered the old man.

Jackie quickly returned his attention to the Boss. “No sir.”

Harrigan said nothing, but his shrewd blue eyes regarded Jackie with interest.


Jackie started feeling a pain in his gut. He tried ignoring it, but one morning he woke up feeling like someone had punched him in the stomach. That’s when the doc told him it was cancer. Reeling from the news, Jackie ended up in an unfamiliar part of town and walked into a small bar devoid of patrons. That suited Jackie fine; he didn’t feel like being social.

“Hit me hard,” he told the bartender, a dwarf who stood on a platform to serve drinks.

“You’ve got problems, brother,” the man said.

“I’m not here for tea and sympathy – just pour.”

The dwarf obliged, but then looked into Jackie’s eyes. “Maybe I can help.”

“Can you cure cancer?”

Jackie spoke roughly, wanting the man to leave him be. Instead, the dwarf smiled. “How bad do you want it?”

His face grim, Jackie smiled unpleasantly. “More than I want the cancer.”

“How’d you like to live forever? Disease, injury – nothing could kill you.”

“Pal, I got a tumor the docs can’t do anything about, but you’re gonna make me live forever, huh? Little man, you’re the limit!”

“Think about it: eternal life. Never grow old, never get sick…”

Jackie finished the shot and sat the glass down. “You’re nuts.”

“Maybe… maybe not.” The dwarf held out his hand. “Shake my hand, Jackie.”

“How do you know my name?”

“I said, shake my hand!” The dwarf gabbed Jackie’s hand and held tight. “You’ve just been given a gift. Use it wisely.”

Sudden heat coursed through Jackie’s body, and he took a step backward, closing his eyes. When he opened them, he saw the room was empty. The dwarf – and the booze – were gone.

Dazed, he wandered out into the street, still thinking about the dwarf. He never saw the truck coming…


“Hey, mister, you okay?”

Jackie looked up into the worried face of the truck driver.

“I thought you were a dead man! Your neck, it’s at a funny angle. Hey, mister! Don’t get up! Wait for the ambulance!”

Jackie wasn’t listening. He touched his neck with both hands, made a slight adjustment, and went on his way.

He remembered the dwarf and smiled.


“Baby… baby,” moaned Jackie into Mrs. Harrigan’s raven tresses. “Why’d you make Jackie wait so long?”

Smiling, she draped a silky thigh over his. “It was worth it, wasn’t it?”

“Baby, you know it.” Hot and hard, he was about to enter her when he heard the sounds of gunfire. Pain ripped into his back and buttocks and he collapsed atop the screaming woman.

Sliding toward oblivion, Jackie heard Harrigan say, “Get the body outta here. You know what to do… they’ll be pouring the concrete tonight…”


His mind foggy, Jackie slowly came to, aware that something wasn’t right.

His face… something was all over his face…

He struggled without success to move arms and legs. He tried to open his mouth, but something was clogging it.


And lots of it, packed tight.

The irony then stung him and he wanted to laugh; instead, tears leaked from his eyes.

Harrigan was right: it was good to have friends in the construction business.

As for Jackie, he had immortality.

Beneath concrete and six feet of dirt.

Word Count: 762
Photo: James Cagney, Movie Actor

Author’s Note: This story is written based on a challenge issued by ThainInVain to write a flash fiction based on the prompt ‘Infinite Jest.’ I certainly went over 500 words, but the story was inspired by the prompt, so I’m crediting ThainInVain for the inspiration. ThainInVain’s weekly challenge can be found here. Be part of the challenge!

About Kate Loveton

Aspiring novelist. Avid reader of fiction. Reviewer of books. By day, my undercover identity is that of meek, mild-mannered legal assistant, Kate Loveton, working in the confines of a stuffy corporate law office; by night, however, I'm a super hero: Kate Loveton, Aspiring Novelist and Spinner of Tales. My favorite words are 'Once upon a time... ' Won't you join me on my journey as I attempt to turn a hobby into something more?
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30 Responses to Infinite Jest: The Story of Jackie O’Rourke

  1. Lucy says:

    How did I know he would have an ironic eternal life? Cause he’s Cagney that’s how. Smartass with a spiritual gift. Good one Kate my sister Grime. Lucy

  2. markbialczak says:

    Be careful what you shake on, hey, Kate? Wonderful lesson in your little morality play. Well done, my friend.

  3. speedodoyle says:

    Gave me a shiver, or more than a shiver, a proper wiggle went down through me just at the end! Thank you!

  4. What a story! Jackie scares me… You’re good, Kate, dang good.

  5. Helen Espinosa says:

    Brilliant! The atmosphere you created was dizzying… (I was going to say ‘everything’ but it sounded so wrong coming from me. I’m not sure dizzying sounds much better, but it’s all I had) 😉

    You have a fabulous way with words, Kate. I always look forward to reading your posts.

  6. I wonder if the Hamlet-esque theme through this story was something front and centre in your mind when you wrote this. ‘Infinite jest’ is part of a line from Hamlet, and I found myself drawing comparisons between Jackie’s story, Hamlet’s Uncle Claudius who covets King Hamlet’s wife and eventually marries her and the ghost that visits Hamlet (the dwarf at the bar.) Jackie, as in a similar vein to Hamlet, meets an untimely demise in the end!

    Superb stuff as always, Kate! ❤

    • Kate Loveton says:

      I am familiar with the line – it’s a great one! That guy, Willie Shakespeare… he sure had a way with words, didn’t he? 😀

      I didn’t make a conscious decision to craft a story around Hamlet. I was going for something that was ironic and, at the time, had been reading something about Boston politicians in the early part of the 20th century. The first draft of the story, which I had to severely truncate, was more about Boss Harrigan and his doings.

      Having said that, I’m intrigued by the comparisons you’ve mentioned. Maybe I was more influenced than I thought!

      Thanks for the kind words, my friend. ❤

      • You’re more than welcome Kate 🙂

        I did pick up on several similarities between your story and that of Hamlet, so perhaps Shakespeare influenced the direction of this story unconsciously for you. Either way, it’s a cracking story! 🙂

  7. Pingback: Flash Fiction Challenge – Week 37 Submissions | Thain in Vain

  8. Pick your own superlative, Kate — a good one, of course. I’m with John; although you packed a great deal into a small space, there is so much potential with this story. Well done.

  9. That was killer good, Kate! And OMG buried alive! I totally enjoyed the dwarf with the powers to dole out drinks, and immunity! Great work, Kate! TiV

  10. M. C. Dulac says:

    I love the film noir feeling throughout this piece and the great twist! The builders who excavate that site in 100 years will get a big shock!

  11. Kaleiyah-P says:

    Ahh, my goodness. What a super tight-knit piece—“packed tight,” I should say. Right from the start, I know Jackie gets himself into trouble, but the build up was so worth it. Awesome, awesome work 😀 !

  12. willow1945 says:

    Kate, you are master of the surprise ending–I SO didn’t see this one coming! Very well done, lots of twists and turns packed into a short story; very entertaining!

    • Kate Loveton says:

      Hi Willow, glad you didn’t see it coming. I wanted to write something that had a bit of irony to it. When I started writing about ‘Boss’ Harrigan, I saw him as an old wheeler-dealer ward politician who could dispense contracts at will, which then gave me the idea of the construction company – run by some fellows who wouldn’t ask questions. That sparked the idea of poor Jackie buried forever beneath the dirt. 🙂

  13. Fun post. Nice job as usual 🙂

  14. This flash fiction, Kate, of fewer than a thousand words could easily be a full-length novel if you cared to flesh (without padding) because there is just so much good material here, material that holds from top to bottom and is a genuine pleasure to read. Yes!


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