Josh: ☆ - happy headcanon
This man cried tears of joy holding his firstborn for the first time. Could barely make out her perfect little face because he was crying and it was blurry and Donna's mom has an adorable picture of the two of them with the baby and a fully red-eyed Josh. It's Donna's absolute favorite picture to show people when they ask to see a picture of the baby. Sam and CJ tease him about it, but only because they find it really cute actually. (And when they get a chance to hold babygirl themselves, they lose all right to mockery cause tears are flowing all around.)
Josh: ☮ - friendship headcanon
There is no time and there is no distance that can actually fundamentally change the relationship between Josh Lyman and CJ Cregg. After the Bartlet administration, she can hide out in California as long as she needs to, and when she comes back to DC Josh is right there and it's like no time has passed (other than the grey hairs they're both gonna be teasing each other about). Josh could fail to keep up any sort of contact for the entire time he's Santos' COS, and if he calls her again after missing a few birthdays, it's like picking up the phone to an old high school friends and feeling like everything is right as is used to be. They are simply never not going to be them, even to others it seems like they haven't been for years. They really are like siblings that way; doesn't matter what's gonna happen or how long it's gonna be until the next time they see each other, when they do it's just okay again. (Preferably it never lasts very long.)
Josh: ൠ - random headcanon
This got sad but. His father got him a nice tie when Josh told him that he was going to run a campaign with Leo McGarry. Nothing that special or anything really, just a nice gesture and a little teasing "if you're gonna work for McGarry, you gotta dress better than this" knowing Leo's peculiar about his suits. It's a very nice tie. Josh was planning to wear it for the DNC that year fully convinced from the start that Bartlet would be accepting the nomination there. Instead, he thought about wearing it to his dad's funeral, didn't end up doing that because that's not what it was intended for. The tie's in his office in the west wing still, among a few other spare ones he keeps there just in case he spills things or sleeps in the office yknow, but he always finds any excuse to pick any of the other ties. Never ends up wearing it while working for Leo. (But he wears it to Leo's funeral. Cause you know, you gotta dress nicely for McGarry. He cries when Jed compliments the tie just to be nice.)
Leo: ☯ - likes/dislikes headcanon
This is the silliest thing, but Leo doesn't like the President's chili. He is too much of a food snob to actually love the taste of the chili Jed brags about but that Zoey and Charlie are haphazardly adding spices to in the kitchen when he's not looking. He loves the evening, he loves the moments where Jed's serving it, he loves Jed (and it's a testament to the friendship that he will never say this thought out loud), but he does not like that chili. He does in fact kind of look down on Josh and CJ respectively for genuinely thinking it's like incredible food. It's not. It's very average chili and that's pushing it. He's going to take this opinion to the grave (but Jenny knows).
Leo: ☮ - friendship headcanon
He and Angela Blake have stayed in pretty regular contact over the years. Even though they rarely work together anymore, he really does appreciate all she did for him during his time at the Labor department. Specifically, when he was secretary of Labor and she was his 'second in command' I'm assuming she was his COS or something? And given this was the exact period of time he was first still actively drinking and taking valium, and the time in which he went to rehab without anyone finding out, I think she (and Margaret) played a big role in that. That's not the kind of thing she can ever get public credit for, and they're not the kind of people on dwell on these things and get emotional; they rarely if ever as much as mention it. But she's one of the few people who he remembers writing and buying something for Christmas without Margaret reminding him (an honor not extended to both sisters LMAO), I headcanon she made sure to check in both personally and to make sure if there was anything he needed her to say/not to say when Lillianfield outed him as an addict, and this is a key reason why she was his first call during Zoey's kidnapping and when he needed someone trustworthy to take over part of Josh's portfolio on a whim.
Leo: ▼ - childhood headcanon
He's the middle child between his two sisters, with one being a few years older than him and one being just a year younger, but his dad instilled that idea of the man of the house in him from a very young age. He was his dad's favorite (and the only one of the kids who knew about his dad's affairs before their mother eventually told them after his death), even though Leo's feelings about his dad were Complicated at best. He loved him, and he was always closer to his dad than his mom, but he hated his drinking and was sometimes scared to see him that drunk (and never stopped thinking about the irony of watching Mallory have exactly these feelings about him later). He never actually held the affairs against his dad? It wasn't a particularly big deal to him? But he hated his dad sometimes for the drinking. But also he was his favorite parent, and always stayed it. When his dad died, Leo took that mantle of the man of the house very seriously, even though he wouldn't even live at home for much longer, and even though especially his older sister had her problems with it both for his sake and hers, and just !!! It was a very complicated family dynamic. But he loved his dad, dammit, and he hates that he became him.
