August 16, 2025 11:35 PM (GMT+2) I never really got around creating this mystery and just wrote all of my thoughts in the event Passing / disappearance of Simon. However, I’ve been thinking about it enough to grant it a mystery entry. It really is something I’d like to see solved before I’m done with my adventure. For organizational purposes, I’ll be moving all the relations in the event to this mystery and will continue the speculation here. Below is all previous speculation.
July 16, 2025 12:20 AM (GMT+2) I actually have no clue when he died, but he must’ve died at minimum before Mary wins Herald literary honor.
This is due to the following text:

Perhaps he died before Passing of Clara. So far I’ve found no evidence of his death inside the manor, like a note mourning him like with Clara and Herbert. In reality, with my current evidence, he may as well have died anywhere between 1952 and 1985.
July 19, 2025 11:17 PM (GMT+2) Actually, after learning about the Birth of Mary, the year Simon died is now between 1958 and 1985.
August 16, 2025 12:27 PM (GMT+2) After new info from 6th red letter, the possibility now opens that he’s actually not dead, or at least that he was not necessarily dead at the moment of writing of that article (the one in News snippets at the archives). That’s because there’s a strong possibility he “disappeared” in a similar way to Mary Matthew Jones (Marion Marigold), since according to Herbert S. Sinclair she ”followed her father’s footsteps and made the same sacrifices he did”. I’ll be updating the title of this event to reflect this.
August 16, 2025 11:00 PM (GMT+2) Since Letters from pigeons are only addressed at Clara Epsen, I will say that Simon was already not around at that time. So that puts his death / disappearance between 1958 and 1974. For now, I’ll arbitrarily choose 1966, the middle point. This incidentally would make Mary 8 years old when he left, in the same fashion as Simon when Mary left.
August 25, 2025 8:58 PM (GMT+2) I still haven’t fully translated it, but according to Clara’s message translation, it seems possible that Simon H. Sinclair left to go live in her house in Eraja. Also, under the assumption that my interpretation is correct, she gifted him said house, and as such he must’ve still been alive by the time she passed. As such, this would put his death / disappearance after 1983, which would contradict my previous conclusion. There’s two ways to solve the contradiction:
I find (b) a bit unlikely given the tone of the letters, but if (a) is correct now I have more questions than before.
August 27, 2025 1:20 AM (GMT+2) In Clara’s sleep diary, she refers to him as her “late husband”, implying he is actually dead. So my crazy theories might’ve been wrong after all. I also probably misinterpreted Clara’s message on her tomb. I’ll be reinterpreting it with the new knowledge that Simon was dead.
In any case, none of this narrows down the date when he died more than I already knew.