An interview with Paul Ryan O'Connor

Author of "Whitey's Elephant"

Hello, Callers! Thank you for being here.

To close out 2025, Paul Ryan O’Connor sent us the perfect story for the holiday season. In Whitey’s Elephant, a group of mafiosos attempt a white elephant gift exchange. But these wiseguys might not be the right crowd for a game built around ritualized theft and backstabbing…

O’Connor joins us today to talk about his writing process, influences, and why the first rule of being funny is “don’t try to be funny.”

Be warned, there are spoilers ahead.

COLD CALLER: Tell me a little about your path as a writer. When did you first start writing seriously? How did you come to focus on the crime and mystery genre?

PAUL RYAN O’CONNOR: I’ve always made my living as a writer, but I’ve never been a writer for a living. I spent forty years in the video game business, and that meant writing every day — design documents, property bibles, interstitial scripts, excoriating emails, and endless pitch presentations. But no prose writing.

I’d be disappointed in myself if I died without publishing a book. When my 60th birthday came around a couple years ago I figured I’d better get started.

I settled on genre fiction because I “wanted things to happen.” I’m not confident I could write literary fiction about an existential suburban crisis. Add a murder, then, sure, I can do existential crisis all day. Mostly I’m interested in how characters behave under pressure, and crime fiction gets me there quickest.

The transcript format made your story stand out immediately as I was reading submissions. It also turns out to be a central piece of the plot; the transcript itself is an artifact of Sonny’s betrayal. I’d love to hear more about how those elements fell into place. Where did this idea begin, and how did the story change or grow over the course of revision?

“Whitey’s Elephant” came by working backwards from a since-forgotten market call for holiday mystery stories. I thought of holiday traditions, then of white elephant gift exchanges, and then naturally of Whitey Bulger (as one does).

The title pushed the story like a rocket. I knew the elephant would be central to the story, and flashed it would contain a surveillance device. The conflict would come from some dumb mobster trying to fob off the elephant onto his boss through a white elephant game.

Telling the story as a wiretap transcript puts our attention on dialogue, where the life of the story resides. It also lets me conceal the duplicity and interiority of the characters — not that these mooks have much of an internal life — and I liked the serpent-swallowing-tail structure of a transcript being an artifact of its own story. I read some John Gotti wiretap transcripts and went from there.

The other thing that made this piece stand out is how funny it is. What advice do you have for writers who want to use more humor in their own writing?

My advice is don’t try to be funny! If your story wants to be funny, it will tell you. Once I had these knuckleheads doing a Secret Santa routine it was obvious the story would be comedic.

I tried to not tip over into farce. Like with any writing, you need to take stuff out. Service your tropes, but don’t become trope service. None of my guys say “Fuggetaboutit,” and that’s deliberate.

Who are your big influences? Were there any writers who influenced this particular story?

This story springs from television and film. I’m a 1960s kid from the San Fernando Valley. Where am I going to meet wiseguys? “Whitey’s Elephant” comes from watching too much Sopranos and Goodfellas. I don’t pretend that it has the slightest authenticity. These are pop culture gangsters.

More than any other story we’ve published, your dialogue is doing a ton of work to establish character, relationships, and background. How do you strike the right balance of weaving that information into your story while still making this feel like a real conversation?

It’s a rhythm. You have to hear it while you’re writing it, and it has to sound right when you read it out loud. My neighbors heard my bad Jersey accent all day when I was writing this.

The transcript format lets me cheat by identifying who is speaking on every line, which means the guys can talk alike without the reader getting too lost. Mostly I just tried to know the guys, know who liked who, understand the hierarchy in the room, know who was a hothead and who was stupid. That gave me a kind of chorus where I could pick the right guy to say the right thing at the right time to push the story along.

You’re also a very prolific writer. What’s your writing routine like? Do your writing habits differ from fiction to nonfiction?

Thanks for calling me prolific! I’m ruled by insecurities, as writers often are. Writing has been my daily job now for about 3.5 years, and in that time I’ve sold fifteen short stories. I’m negotiating a contract on my first novel, and I have a second novel going out early next year. Is that prolific? I feel I should have done more.

I’m driven by routines. I work five days a week, mostly take weekends off. I get 1500 words a day, rain or shine, which usually takes an hour or two, but it can take all day to get that hour. My word rate used to be lower — I had to build up to it. I used to endlessly revise as I went, which limited me to hundreds or dozens of words a day.

Now I do an outline, followed by a machinegun first draft with no looking back. I let the first draft sit for weeks or months, then do a new outline while re-reading. The second draft is a full re-write from a blank page, treating the first draft as a kind of 1:1 map of the project, as Matt Bell put it in Refuse To Be Done. My third draft is where I put everything under the microscope.

I don’t write non-fiction outside of my blog, which publishes a couple times a month, and which I write on the margins of my “real” writing time. A lot of my blogging is about routines, tools, techniques, word rate, and the endless angst of tracking metrics — https://www.paulryanoconnor.com/by-the-numbers

Did you have any mentors or particularly influential teachers that helped you find your footing as a writer?

I’m a high school dropout. I patched together an AA degree years later, but I don’t believe my formal education influenced my writing in a substantial way.

My teachers were writers. Hammett, Chandler, Ross Macdonald, Robert B. Parker for detective fiction. Elmore Leonard. I gravitate toward opinionated and voicy writers like James Ellroy, Hunter S. Thompson, and Joseph Heller. I read a lot of science fiction and fantasy as a kid — I obsessed over Roger Zelazny’s Amber books, which kicked off my love of hardboiled first-person narrative. I love pulps.

I spent 2025 as an Edgars judge, which meant I had 200+ books shipped to my house. Plenty of good books, but I found vanishingly few comps for my own unpublished novels. I try not to dwell on whether that’s a good thing or not. Am I fatally out of step? This job requires a certain indifference to results. I give everything to my work, but once it is submitted, it is out of my hands. I can’t control if editors will buy it or readers will like it. That’s up to them.

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Paul Ryan O’Connor is a frequent contributor to Ellery Queen’s Mystery Magazine, where his debut short story — “Teddy’s Favorite Thing” — was voted a 2023 Readers Award, and earned a Derringer nomination from the Short Mystery Fiction Society. He has also been published by Cold Caller, Mystery Magazine, Pulp Asylum, and Shotgun Honey. Before turning to a life of crime (writing), Paul spent decades writing for video games, most recently as Game Director for Amazon's Lord of the Rings MMO. Paul is an active member of the Mystery Writers of America, and lives in Carlsbad, California, where he perpetually re-writes his first novel.