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- "She's a wilful girl, not always the easiest of staff, but nevertheless, I don't want to see her suffer for her impetuousness."
- ―Caroline describing Rose, 1711.[src]
In 1711, Rose absconded from work to visit the Auld Shillelagh, where she was encouraged to drink heavily by Tom Cobleigh, his son Seth and their associate, Julian. Unaware of the men's dishonorable intentions, she drank herself into a stupor. As the men attempted to escort her from the establishment and have their way with her, Edward Kenway intervened, having caught on to their plan.
A brawl subsequently broke out, which was ended by the arrival of Caroline, Emmett Scott's daughter, who came to the tavern to fetch Rose home to the Scott residence. Later, at the market, Rose was asked by Edward, whom she initially did not remember, to assist him in his courting of Caroline. She subsequently began giving him valuable information on Caroline's habits and routines.
During her time as a housemaid for the Scott family, Rose saw Caroline get married and move out, then move in again due to marital troubles and eventually perish in late 1720 after she had contracted smallpox; Rose herself had been innoculated, along with the rest of the staff, and thus avoided being infected. Part of the blame for Caroline's death lay with her father Emmett, who had refused his daughter proper medicine, for which Rose resented him.
When Edward returned to Bristol in 1723, Rose met up with him in the market and revealed that Emmett, whom Edward planned to assassinate, would be in his warehouse that night, as she had been ordered to bring him fresh clothes at his offices. However, upon entering the warehouse, she was taken hostage and made to stand on makeshift gallows, with only Wilson's hold on her preventing her from being hanged. Edward subsequently came to her rescue, killing Wilson and Emmett.