#were they more drawn to the exoticism of caroline's british aristocracy
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do you think stewy used kendall when they were kids? or did they mainly just fuck around until stewy actually grew up and became a "vampire locust fuck." and realistically, do you think stewy is someone actually capable of love or is it just a complicated mixture of nostalgia and self-interest which manifests in "the friend card"
No, I don't actually.
I think that for a few reasons, first because they were likely very young when they met, and second I think that when they met, the disparities in their family wealth and power likely weren't as extreme as they became when they were older.
A lot of this comes down to timeline. I've been working on one for the show overall based off of all the bits of context and firm dates that the show drops on us, which I promise I'll actually post one day in its entirety, haha, but I think there are a few bits of information here that are important to your ask.
Firstly, we know that Kendall and Stewy went to Buckley together, which is likely where and how they met. Buckley is a real place – it's an elite Manhattan private boy's school which starts in kindergarten and goes up to ninth grade, so assuming that they started in kinder together, they likely met when they were only four or five years old.
(The rest is below a cut because this got a bit long!)
Meeting at that age, and particularly in a space of relatively-equal privilege such as an elite private kindergarten, is, I think, a pretty protective space. They're in a bubble together, and it's one where they have the same resources, the same sorts of toys, the same sorts of homes to return to. At that age, in a space of shared wealth, I think they would've felt their differences in other sorts of ways – Kendall had lots of siblings! I think it's kind of implied Stewy's an only child! Kendall has a much older brother with a different mother! They both have parents who are immigrants, but from very, very different backgrounds in terms of race, culture and class! In particular, Arian has spoken about Stewy having a level of generational wealth in his own family, where as Logan's come from poverty and Caroline aristocracy.
Of course, they're not going to be thinking all of those things in that many words at elementary school, but they do inform their characters, and I do tend to think that Stewy's more comfortable around wealth and the wealthy because of that background, while Kendall has inherited some of his dad's nouveau-riche insecurity.
The other big factor is that I think Logan's empire was really still growing when Kendall and Stewy were kids.
In terms of my timeline, I think we can generally guess that Kendall and Stewy were born in 1979/1980. This comes from the fact that s1 is explicitly set in 2018 and each season seems to be around four to six months, meaning Kendall's 40th birthday was likely late 2019 or early 2020. This would put Kendall and Stewy in kindergarten at Buckley in 1984/1985, and 1985 is a year with a significant canon mention. It's the year Logan took out the large debt to expand into cruises and parks.
To me, that's a pretty significant marker of the broader Waystar expansion that saw the company (and Logan) develop their cultural and political monopoly. It was likely that there were some teething years as the business stabilised too, so we can probably assume that business wasn't really booming until - - let's say - - 1988, and how that was received by the broader New York elite aka the other parents at Buckley, is anyone's guess.
My point is, is that while I think Kendall was always a little prince, Stewy was one too, and for most of their childhood and adolescence, they were in a little bubble where everyone had their family kingdoms, and it was likely not until college when they were faced with a greater mix of people from different social classes and background that they really felt their own, and each other's, social power. By that point though, I think they had twelve years of real friendship and history that meant any way they might've used each other was something that was mutual.
And I do think there's real love there between them. Arian has said so himself after all, but I think we see it in the show too where there's really human feelings beneath the business machinations for both of them. There's Stewy's guilt after abstaining from the vote of no confidence, as seen mostly in the Prague episode, but also I think in the way he watched Kendall during the vote, and the next time he was present with Logan confronting Kendall, he put himself between them. Don't forget after all, that Stewy tried to get Kendall out before he pulled him into the deal with Sandy, something that Kendall pretty clearly needs to do.
I think there's been real hurt a lot on both their parts too, and that's all tangled up in that history and that idea of what a future could look like, and I don't know! They both always keep the door open for each other, and I don't think that's just professional. If it was, Stewy's shown he can't really be trusted and Kendall's shown he's unreliable and manic at best, and yet they both seem to keep the other high on their call list, as s3 reiterated again with the trojan horse and the stakeholder vote, and I don't think nostalgia or self-interest is enough to keep that path to one another clear.
Is it a pure love? No, I don't think so, but I do think it's real. Stewy wanted Kendall out of a business he knew was killing him, he offered to be a friend first in a moment that really mattered, he refused to take Kendall's board seat when Logan offered it as a sort of vindictive prize – all of those choices are being driven by something deeper than professional self-interest, and I love it and them in all their complexity and messiness.
#this actually really got me thinking about how caroline and logan were seen by the other parents at buckley#because these are all rich kids right?#were they more drawn to the exoticism of caroline's british aristocracy#and the sort of appeal in romanticising that and seeing it as a validation of logan's self-made man?#or do they see logan as an embodiment of the american dream#a rags to riches story#and feel more drawn to and curious about him?#i kinda feel like it would be the former?#like there's a snobbery from old money around new money#and i can kind of see that as adding to the chip on logan's shoulder#he'd never socialise with them anyway of course#but i can see it as being the kind of thing kendall shiv and roman would all internalise too#kendall x stewy#kendall roy#stewy hosseini#speculation#timelines#hbo succession#succession meta#welcome to my ama
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