So I’ve been thinking about this for a while (see initial post) and I actually had these conversations with my moot @elderawesome plus a 3 week old dm I sent @emptyingthespiral that never really went anywhere
Personally, I don’t think the background you’ve given Simon as it is would be something that Fitzroy would approve of for the Sierra program, let alone the CIA and Golf Sierra. Setting a domestic terrorist loose to do basically international terrorism and assassinations is generally not something that would get approved by anyone, deprogrammed from a cult ideology or not.
I propose: third gen military brat Simon. Now, this is definitely more book canon than movie canon, but putting Simon in Golf or Whiskey Sierra via the military -> CIA sad team pipeline feels the most on brand for him. (Especially if you wanna bring the COI into it.)
Why military brat? Because the US military is a cult in and of itself; Simon would be under a tremendous amount of familial pressure to enlist as soon as possible, especially if you set it in the 2000s/the Second Gulf War/the Iraq war like it is in the books.
So Simon grows up in the middle of ass nowhere America (I like Montana for the Eden themes, Texas is a close second, but the entire agrarian midwest would work fine with their “God, Guns, and Grain” ideals) with his vet father and nurse mother teaching him how to shoot, and stab, and dress wounds—ostensibly for hunting, but he knows better. He enlists in the Army and ends up training as a field medic.
This, more than anything else, teaches him how to lie convincingly. It’s also where he could get the nickname Butcher, but I haven’t explored that idea much.
He gets shuffled onto Golf Sierra in 2004, a handful of months before Court gets burned and they’re ordered to hunt him down. Simon, loyal to a fault but seeing the writing on the wall, also flames out.
Maybe they both end up at Fitzroy’s, working parallel to each other but not together, or maybe they end up in completely different places.
Simon goes into intelligence gathering and long term ops that require pretty deep cover. It keeps him from thinking about his parents and how furiously disappointed in him his father must be. He becomes a man of many names, but never his own.
The CIA gets to him in 2008, and tell him that he can do this op for them and they’ll rescind the shoot on sight or they’ll, ya know, shoot him. He does the op because he really doesn’t have a choice. It’s a long term op that takes him basically a full year to complete—intelligence gathering in an international prison, he nearly dies, maybe he loses his arm?—but he recovers from his injuries and get shuffled onto Whiskey Sierra just in time for them to basically do the same thing to Court (see: book 2 On Target).
To answer the question you posed in phmcord, Simon would be a navigation, optics, infiltration specialist. (<- which also wouldn’t work if he was previously a domestic terrorist, but I digress). He has a preference for knives because they’re lower profile than guns, but he is proficient with guns and he knows his way around poisons.
