#1 COURTLAND GENTRY APOLOGIST

COLTLAND TWINS + OLDER BROTHER COURT

imagine, Six is kinda the best of the best in the Sierra Program so he often gets ops that are harder/more time sensitive or important than the other Sierra agents. not to say he gets slack from anyone higher up — quite the opposite actually since he’s so good at his job — but he’s also the youngest of the Sierra agents. ergo, he gets a bit more time with like Fitz or his teachers during his early years training to be an asset.

Six is insanely good at his job. he likes the thrill and he likes that he’s good at it and he likes being out of that damn jail doing something even though he’s trapped by the CIA in an invisible prison of his own choosing— because at least he’s out. he’s never really gotten over killing his dad for his brother in however many years it’s been since he was put away, but at least it’s easier to push aside when he’s taking out targets that are downright Bad with assurance from the government at his back.

and then there’s Fitzroy and Cahill. i imagine them to have worked together for years as both coworkers and now trusted friends to where Fitz would’ve let Cahill in on the Sierra Program as off the books as it is. she’s almost Fitz’s unofficial right hand when it comes down to it, and the same goes for him when it comes to Cahill’s jobs too. it’s Fitz who ends up introducing Six to Cahill, likely during some big op or something.

in front of authority (especially strangers) Six is pretty straight laced and no-nonsense, ready for whatever is thrown at him. a lot like Cahill is on a normal day. once she becomes more of a common fixture in Six’s life through ops and other directives he starts to open up and get more comfortable snarking and dishing out pointed dry humor to her much like he does with Fitz after they got close.

Fitz and Cahill have been (more or less) trading off being Six’s handlers. they know him intimately as an asset and even more so as a human being. they see no problem forcing Six to take a breather or an underground mini-vacation when Six starts looking rough around the edges. they know his tells, like when he gets caught in bad memories or when he starts to spiral over how he became a Sierra. they like him, so what?

the weird relationship bit comes in right about now: it dawns on Fitzroy and Cahill during one of these off-mission episodes that they have, in the simplest terms anyway, been co-parenting Six.

it’s not on purpose, really. Six is fucked up enough and traumatized enough that sometimes he just… breaks a little. and when Fitzroy and Cahill notice those rare Bad Days where Six Court can’t keep a lid on everything and it feels like he’s a little kid again and his dad is here he’s coming Court did something bad and dad is gonna make him pay for it—

Margret and Donald see it all and step in and for a moment, and the kid is okay again. just a little. (Court is a kid to them, i swear. he probably wasn’t born yet before Fitz and Cahill hit their twenties.) Court coming down from and resetting after one of these breaks is often slow and difficult, not that Court himself ever really remembers the process. he gets jumpy, spacey, extra quiet, and tired — all normal things during and after traumatic breakdowns — but he also gets… clingy.

Maggie and Don wouldn’t call it “touchy” mostly because Court can barely handle gentle physical contact on a normal day, but “clingy” is more than accurate. Court will follow them around, sit closer than usual to them, and (if he’s in a stable enough headspace) will occasionally act as their gopher (fetching things) or assistant (paperwork) without being asked. but if it’s a Bad Break Maggie and Don will find themselves with an unresponsive less coherent Court. a wet puppy kind of Court. a 15 year old kid still learning himself and family and love who never truly went away.

Maggie can count on one hand the number of times she has taken charge during Court’s breakdowns to stick him in comfy clothes, force him to eat, or sit him in front of a screen to watch fucking Animal Planet like it’s Cocomelon. she can count on two fingers the number of times Court has fallen fully asleep on her person without realizing it.

Don, as Six’s direct handler and boss, doesn’t get that soft-sleepy post-break Court as much as Maggie does. instead Court gets stiffer, more robotic, and a wandering-lost like he is constantly forgetting he’s not on an op right then. so Don gives him one. he tells Court what normal clothes to wear and where Court will be accompanying him through the day. he gives Court simple instructions and step-by-step directions. more than once Don has taken Court out shopping or for meals (undercover, obviously) to get the kid what he needs without needless pushback while the movement from boring task to boring task wears Court’s body down until he’s more of a relaxed-tired than jumpy-exhausted.

Court is the very last of all of them to realize how caring Maggie and Don have become to him, and even then he refuses to believe it’s out of anything but up-keeping a friend-like asset. Maggie and Don on the other hand have already worked out a schedule and funds for who gets Court and when between Six’s missions.

yeah, Six is an asset and almost 40 years old or whatever but Fitzroy and Cahill like him too much to stop caring now and quite frankly it would be a pain in the ass not to keep him close by and tempered— especially once Claire meets Six and has him wrapped around her finger.