Okay, now I'm really curious to know who you think J.S. is (if you don't mind sharing that, of course)
I am thrilled to talk about this! So thrilled I waited to respond to this until I had a proper keyboard.
So. Much like ‘what is in the sugar bowl’ and ‘what is the schism’, ‘who is J.S.’ is different depending on the context and the person, but there is also clearly only one actual answer because there is a specific sequence of events that we’re particularly curious about. (This got really long! Actual answer below the cut.)
The ‘who is J.S.’ question is a little more complicated because it’s less clear which time the question is asked is the most valid. I always think it is when Klaus decodes the Verbal Fridge Dialogue, but it could be when Kit asks the Baudelaires to learn who J.S. is. Since this is what I think, I’ll go with the first question. And the answer to that (and while I think there is pretty good grounds for supposing this, also don’t really care) is Lemony Snicket.
I believe whomever (I’m going to continue to assume R/the woman in the diving suit over Kit, because I think it makes more sense, and I don’t believe Dewey was working only with Kit, but the way he phrases it does kind of make it sound like Kit, but there are other things that make me think it’s not Kit, but that’s not the point) through the sugar bowl out the window knew that Lemony Snicket (following VFD tradition as established by Sally Sebald) would pick up his older brother’s affairs, and left the message addressed to Jacques assuming Lemony would find it (why? maybe Lemony is presumed dead by too many people and it would look suspicious to leave a message for him, or actually, this is VFD, so I think it was a deliberate attempt to exploit the number of people with the initials J.S. to create confusion).
Further along those lines, I think Lemony was on Mount Fraught at the same time as the Baudelaires. He received the message that was meant for him, possibly as little as hours before the Sinister Duo burned the library, and did something to ensure that the passages Klaus would need to decode the message survived the fire, as he already knew that the Baudelaires were heading in this direction. (I worked this out for a fic I’m trying to write... I’m pretty sure it works.)
If we suppose the second question in the Penultimate Peril, the answer is still Lemony Snicket. Since Kit is in on the plot to get the sugar bowl, she already knows this. But I think she is also sincerely asking the Baudelaires to investigate because she knows there are multiple J.S.s and she doesn’t know how many of them are trustworthy. I don’t think Kit is in on what Justice Strauss and Jerome Squalor (they are valid and correct answers to ‘who is J.S.’ but not the actual answer). Primarily because the trial does not happen on Thursday, so it is not the why the volunteers are gathering at the last safe place. I’m not entirely sure what to make of the trial; I don’t know how early it was corrupted by the Sinister Duo and I don’t know what portion of V.F.D. knew that the Sinister Duo were the High Court, but I do know that the trial wasn’t on Thursday. I also believe Kit and Lemony (and probably Dewey and R, but that is less clear) would be far to jaded to confront Olaf in such a direct fashion, so it just doesn’t really add up.
We also know that Justice Strauss was the one following Kit when she drove through the hedge, so I think that is good evidence as well that they were not working together. Even though both Justice Strauss and Jerome Squalor seem to know about the sugar bowl and it’s importance, I don’t believe either of them know what is inside it. And I don’t believe they were working with Kit and Dewey (and Lemony and R (who may or may not be the woman in the diving suit)). (Also, Lemony was obviously the taxi driver--I don’t know why he said what he did to the Baudelaires. I’m certain he knew who they were. My most likely answer is that he did not want to encourage them to come with him--he did not want, and did not believe their parents would want, for them to be tangled up in whatever he had to do with the sugar bowl next. I’m not sure if he regretted it.)
How is this so long? What did I do?
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