A conversation about the writing journey of Penna and Silbrith.
Current projects: Penna is writing a Caffrey Conversation story.
Silbrith will post Dances with Dinosaurs (Caffrey Conversation) on May 23.

Banner: Will Quinn

Tuesday, September 24, 2019

A Win-Win-Win Situation

In Night Music, the demon Crowley obsesses about a threat to his well-being. He's convinced that Winston-Winslow, a private investigation firm usually abbreviated to Win-Win, is actually a front for the Men of Letters and that Henry Winslow is a cousin of the Winchester brothers. I'm flattered when readers ask if I'd planned Crowley's Win-Win-Win nightmare from the beginning. I wish I could say I was that farsighted but it was a case of sheer serendipity. The more I thought about it, though, the less convinced I became. Could supernatural forces have played a role? In my search to discover the truth, I decided to interview the creative genius behind the Caffrey Conversation AU, the one and only Penna Nomen.


Me: Did you have any ulterior motive when you chose Winslow and Winston for the names of the two ex-FBI partners who founded Win-Win in the early 1960s?

Penna: No, I was trying to think of a new alias for Neal that was distinct from the ones in canon. I wanted something that started with "win" and Winston and Winslow came to mind. I'd picked Winslow for the slow-but-steady connotation of "win slow," but later struggled to remember which last name I'd chosen, so as I would need to write the name, I'd be thinking, is it Winston? Winslow? Winston Winslow sounded like a company, and it felt natural when I wanted to name the family company. And of course Win-Win was such a fun shortened name to use for them. I wouldn't have picked Winchester because with Neal's dislike of guns it didn't feel right for an alias he'd use.

Me: Henry Winchester, Dean and Sam's grandfather, is a canon character who first appeared in Supernatural on January 30, 2013. Your first Caffrey Conversation story was published in December 2013. Crowley insists on knowing if you intended to torment him by giving two Winslows the given name of Henry.

Penna: Nope. From a timing perspective, I chose the name Henry Winslow in the spring of 2013. I didn't start watching Supernatural until at least a year later. The fact that Henry was named after his great-grandfather was inspired by Robert. His obsession with taking over Win-Win led to the realization that, of course, he would have named his son after one of the company founders. At the time I chose the name Henry, I also didn't realize that Matt Bomer has a son with that name.

Me: What about your choice of Jensen Ackles to play Henry?

Penna: After changing my mind many times about the actor to cast as Henry, I thought I was safe with Jensen as someone who hadn't been on White Collar and that Dean wouldn't be joining the cast. I was more inspired by Jensen than by Dean—the actor's sense of humor and love of music were big factors in the choice.



Having laid to rest the notion that Penna deliberately chose the names as foreshadowing for a possible future story arc, the question remains if an unknown entity was guiding her subconscious. How else to attribute all the parallels? All those "Win"s? Three men named Henry? A private investigation firm known for its secretive methods and reliance on psychology and technology? The headquarters of the Men of Letters was destroyed in 1958. Less than five years later, Win-Win was founded. Simply a series of random coincidences? Crowley thinks not.

It's been my pleasure to take those seeds and grow a nasty conspiracy theory to haunt Crowley's dreams. My original intention was not to carry it any further. I also didn't initially plan to actually write Arkham Files stories. I assumed Diana would simply reference them. Now, I've published six stories and am editing three more with the end nowhere in sight. So much for intentions. Henry and Crowley have unearthed a common ancestor—Seth Winslow/Winchester. Will Crowley's fear of the Men of Letters being involved turn out to be true? If history is any judge, he shouldn't relax his guard.

Night Music on Archive of Our Own
Night Music on FanFiction





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