Put “📓” or some other version of a book emoji into my inbox and I’ll explain the plot of a fanfiction that I haven’t written but daydream about.
From what I see of CR fandom there's ... well frankly, not a lot of thoughts about Cassandra de Rolo, which is a shame because she's fascinating, but there seem to be a few specific trends for her. Some people want to give her a chance to be awesome and adventure on her own, which fine, I kind of get but also I think after the five years she had she'd want to unwind and relax and be safe more than a lot of things. Even when dealing with anger and all (with Percy's help, given some of the Wrap Up comments) I don't think that's necessarily the route she'd go. The other trends I see for her are often specifically romantic - and there's two trends I see there. People who ship her with Kynan, due to some of the Wrap Up comments from Matt, and people who ship her with Kaylie for... I don't know what reason. Some combo of Lesbians and, from what I could tell "it'd piss off Percy and that'd be funny" which I don't necessarily believe and certainly do not find encouraging ship motivation.
Sufficeth to say, I do not find either of these particularly compelling.
I've written a small fic about Cass before (here) and one day I'd like to write something that builds on it. Specifically, I want to explore how she might interact with Desmond.
No, not the mapmaker, that's Tyriok.
No, not the person they saved outside of Westruun from the orcs.
The carriageboy Percy maimed.
See, there's a few things I think that have the potential to make that interesting. Firstly, we're told Desmond is around 18 - which is to say, older than Kynan, around the same age as Cass, and likely around the same age Percy was when the Briarwoods attacked.
(Percy's last words to Desmond before knocking him out, "I want you spend the rest of your life making up for what you allowed to happen", suddenly take on a whole load of other meaning when you consider that, imo.)
He's a Whitestone native, he's not an inherently bad person. Percy attempts to apologise once they return, but gets repeatedly spoken over because he pauses, presumably trying to find the right words to apologise ("I'm sorry I maimed you, I was not entirely myself and may have been under the influence of a demon but that's no excuse and I do not know that I can ever make amends to you for the wrong I have done you" is not an apology that's likely to fall easily from anyone's lips, let us be honest here). He does ultimately try to ensure Desmond gets a position of work - which he may otherwise struggle to find, given his maimed hand, and again, which it is only fair Percy attempt to rectify given his responsibility.
But ah, this is all Desmond and Percy, let me move on to Desmond and Cassandra.
They're of an age. They also both lived through the Briarwoods occupation in pretty close proximity to the Briarwoods - Cassandra as their prisoner and Desmond first as the carriageboy of one of their new nobles and then as their carriageboy. They've seen both the Briarwoods capability for kindness, for protective anger, and for their cruelty and brutality - including towards them. They murdered Cassandra's family; when she helped Percy escape they were shot at and she was shot down under their orders. They abandoned Desmond when Vox Machina attacked; on realising he was their prisoner they sent two invisible stalkers to kill him.
They also were twistedly parental to Cassandra and saved Desmond from Tylieri's treatment. These two undoubtedly have complicated, messy and often unclear thoughts and emotions regarding the Briarwoods. Desmond was offered a job as a courier between Whitestone and Emon but after Musician's Nostalgia he's never heard from again. He may have been killed during the Conclave's attack, if he was still in Emon - or he may have been sent off already. The wiki assumes he lives; we don't know for certain. But I like the idea he lives and I like this specific idea, so I run with the assumption he survived and either made his way to Whitestone or was part of the refugees VM evacuated to Whitestone.
And I like the idea that he ends up in service to Cass, basically as her manservant and personal assistant. Percy wants to see Desmond employed. Cassandra is being left in charge of Whitestone and all the things Percy, in his particular messy way, is not good at dealing with, which is to say the aftermath of so much of what he does.
So Cassandra, partially perhaps as a pointed comment, keeping Desmond as her personal servant - so Percy cannot forget what he has done and what he has left her to deal with.
I do not think Desmond would ever think particularly kindly of Percy. I do not blame him. No matter how much I love Percy as a character and think him well constructed and find him fascinating to explore - I would not blame Desmond in the least for being bitter and angry regarding the man who maimed him, never apologised, ensured he was given employment and just left the handling of that to his deeply traumatised younger sister.
There are many legitimate reasons to criticise Percy and Desmond, in this circumstance even more than canon, would have every cause to see those.
But I also think he'd have a lot of reasons to empathise with and understand Cassandra. I think their understanding of the complexity of their personal relationships with the Briarwoods would make them less judgemental of one another's difficult decisions during the occupation; their understanding of the pressures of the occupation and the grief Whitestone and the families within it bear for what happened - they lived in and amongst it as Percy did not.
I think they could connect on an interesting and deep way.
I also think neither is particularly prone to trusting, given everything. I think they'd take a damn long time to admit their trust for each other let alone anything else. If I wrote it, it would be a painfully slow burn.
But... I like to imagine it. I like to think up how they'd slowly be drawn closer just by working together and seeing each other every day and understanding one another's quirks. I like to think about the steady, quiet peace they build because neither has much care for sudden loud noises or explosive anger. For how their understanding of one another builds reassurance; for how that means they stand firm for each other in tentative friendship and empathetic loyalty. I like to think about the way they act towards each other, starting as the formal standard of ruling Lady and personal manservant and how that shifts as they use that to shield one another from things they know they dislike; Desmond given leave when Percy comes to speak to Cassandra, Desmond interrupting with some small important distraction when Cassandra gets caught in panic or anxiety or a memory. Quietly, persistently, helping each other, and it seeming only as work.
But it's too persistent for just work. It's too consistent for work.
But of course - they cannot just admit it. They have little reason to trust, for all they very clearly trust each other within their set dynamic.
This story, if I ever wrote it, would unfold slowly, small thing weighing upon small thing until the pressure is insurmountable and impossible to ignore.
It's not my usual style, that kind of steady slow pacing. But one day, I'd like to try it.