When I decided to turn the Caffrey Conversation into an AU series, I wanted to make my AU a little more upbeat than the TV show. For instance, I wanted Neal to have options beyond working for the FBI or going to prison. One way I accomplished that was giving Neal immunity for his crimes. Another was by giving him a friend who was neither FBI nor criminal: Henry Winslow.
Warning: Spoilers for stories in the Caffrey Conversation AU.
Creating a recurring Original Character (OC) was a risk, as I'd heard that many fan fiction readers don’t like OCs. I countered that by first teasing the Henry character for a while, not actually introducing him but making references that would have readers puzzling about who Henry is. Next, I gave him a role many White Collar fans would appreciate, that of someone who would look after Neal and make sure the FBI wouldn’t take advantage of him. In fact, he represented another option for Neal, the one of holding on at the FBI just long enough for Henry to rise up in his family business and be in a position to offer Neal a stable and interesting job. Lastly, I tried to make Henry a lot like Neal. Twice as much Neal is twice as good, right?
Neal describes Henry as an “alternate me,” someone Neal might have turned out to be if he hadn’t gone into WITSEC as a child. Their mothers were identical twins. Their fathers were both cops with a dark side. Both Neal and Henry felt a need to run away or escape their home life in their late teens, and they spent some time together getting by through cons and playing music. I tried to make them equals in terms of skills. Henry teaches Neal to pick pockets and hot wire cars and play poker. Neal teaches Henry about fake IDs and being a con artist and hustling pool. Henry’s a better musician and an expert in psychology, Neal is an artist and multi-lingual. It’s really a lot like the balance I try to maintain between Peter and Neal – two intelligent men with different experiences and skills who take turns being the smartest guy in the room.
By making Neal and Henry close friends during the time right after Neal ran away from home, I was able to share with readers some information from that time. It’s not something Neal discusses often, but Henry can raise the topic and decide to share information with Peter. In fact, throwing Henry into the mix makes Neal and Peter talk about things they might otherwise keep quiet or not even think to bring up, like in By the Book when we discover the extent to which Peter reciprocates the feelings Neal has for his father figure.
When Henry was embraced by most readers, I was able to use him as a stepping stone toward bringing more family back into Neal’s life. First there are phone calls with Henry’s mother. Then their grandparents visit Neal in the hospital and attend his birthday party, and cousin Angela joins them in a long con. And of course Henry’s father takes his role as a villain.
Henry also made it possible to tell the story Caffrey Disclosure. After Neal faces some of his demons in Caffrey Flashback, I wanted him to help a friend going through something similar in Caffrey Disclosure. The plot I had in mind had this person disappearing and needing to be rescued. I didn’t want to put Peter in that role of the missing person, because then we wouldn’t get many scenes with him. Henry was the perfect character to be rescued, and as Neal’s “alternate me” we could say that Neal was growing up and learning to rescue himself.
Henry likes to complicate things, and often throws me for a loop when I include him in scenes. The most notable example of this was when I tried to give him a romantic interest. I’d thought it would be fun to make him a rival for Sara. Suppose Sara knew Henry first, before she met Neal. Whether or not Sara and Henry ever dated, would Neal be jealous, maybe wondering if she preferred the older, wealthier cousin? But when I threw Sara and Henry together in Caffrey Flashback, there was a distinct lack of sparks. It was the first time Silbrith as my beta told me an entire chapter simply didn’t work, and I rewrote it several times. (Silbrith assures me she did NOT make me rewrite the full chapter. It just felt that way while I was flailing around trying to figure out what to do.) At that point it was in the back of my mind that Henry might be gay, but there was so much going on in the story I decided not to bring the question up. As I outlined Caffrey Disclosure there were a lot of single female characters, and again Henry resisted being attached to any of them. That’s when I decided to start leaving hints of his orientation, which some readers did guess ahead of the big reveal in Caffrey Aloha.
Currently I’m writing a short vignette in the AU about Neal going on spring break and celebrating his birthday. Henry will be there and again he is adding layers of complexity beyond what I initially imagined. Fortunately Neal is able to keep up with him, especially with Peter on his side.
I’ll be posting the story as the first chapter of what I’ll call Caffrey Vignettes on Fanfiction.net and AO3. You’ll see that first chapter, titled Spring Break, in early June.
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