Welcome to my insane conspiracy post about Grelle Sutcliff, her life and her death. This is mostly headcanon and speculation but if you want to read pure, distilled hyper-fixated bullshit, buckle on in.
So, I think the first thing we need to take notice of to place Grelleโs death is her conversation with Othello about the incident 70 years ago in which the Undertaker went rogue. Grelle was not yet a reaper as of this event, but Othello seems surprised to learn of this fact, and based on the fact that Grelle seems to be older than a lot of the other reapers, we know that her death could not have been that recent.
70 years prior to the main timeline of Black Butler would be between the years 1818-19. The incident that occurred mustโve been a very large a event, so for Grelle to know nothing of it means she mustโve become a reaper once enough time had passed for conversation of it to have died down, so to be safe Iโd place her earliest death date as about 1828-1829.
Now this is where it gets interesting. If we push back this date a little later, we get to a very interesting point in history. Grelle often refers to herself as an actress, has quoted Shakespeare and can sing quite well. If we assume these are remnants of her human life, that places her previous profession firmly in the arts.
Well, it happens to be that it was in the 1830s that the emergence of Burlesque began in England. Early Burlesque consisted of a few key elements: comedic parody of classic plays (such as the Greek Classics or, more popularly, Shakespeare), song and dance, and the striptease. Burlesque was considered a crass, scandalous and common art form, and theatres in which burlesque shows were performed were often in the East End.
The burlesque scene would have been a rare occupation in which crossdressing would not have been unheard of, and queerness would have been able to scrape by unscathed. Crossdressing probably would have been used for comedic and fetish purposes, but if in every other corner of society such expression would have been persecuted, it probably would have been a sort of haven for queer people in their day.
Which would make it the perfect place for a human transfemme Grelle to make her home. But this comes with an interesting caveat that I think reflects her relationship with and taste in men: most burlesque performers were probably prostitutes.
If Grelle spent her human existence as a burlesque dancer and sex-worker, she probably would have been used to men showing interest in her, perhaps in an intense and uncomfortable way. If this had left a lasting impact on her psyche, it would explain why she spends her years as a reaper finding men who are uninterested in her most attractive. It also perhaps explains her relationship with Madam Red/Angelina. Having been used by men in her life, it explains why she would find women less threatening to have attraction to her. Perhaps she even began to idealise her relationship with women, and when it happens that these women she finds herself attracted to fall flat of her expectations, she acts rashly. This is why she killed Madam Red/Angelina, disappointed in her failure to match up to Grelleโs hopes for her.
As a side note, we know all reapers must have committed suicide to have become a grim reaper. I think the most likely method of suicide in which Grelle died is that of blood loss in the bath. We know she finds red and incredibly beautiful colour, and what better way to go out than to bathe in the colour herself.
Anyways, if anyone reads this, that is my insane Grelle backstory. Thanks for listening to my ted talk?