キャロライン・スコット・ケンウェイ Caroline Scott-Kenway (1691 – 1720)はエドワード・ケンウェイの最初の妻であり、彼との間に長女ジェニファー・スコットをもうけた。エドワードとの関係を引き離そうとする父親と、アル中気味のエドワードの私掠船乗りになって金持になるという夢のため1713年から彼とは疎遠になった。
Caroline first met Edward Kenway when she rode up to the scene of a fight between him and three men who had attempted to take advantage of a young woman named Rose, one of the Scott family's servants.
Due to her influence, the three men left bashfully, and Caroline helped Edward up and thanked him for his assistance. While Caroline was originally cautious about getting involved with Edward, particularly due to her father arranging her engagement to Matthew Hague, she and Edward eventually fell in love and married some time later.
Two years Edward's senior, Caroline worried about her husband's privateering aspirations and soon grew tired of his inability to find steady work or take his responsibilities as a husband seriously.
His lofty ideas about sailing in the West Indies were the last straw that led to their estrangement; she left their home to live with her parents, much to the dismay of Edward's father and mother, who loved her as the daughter they never had.
Unbeknownst to Edward, Caroline was pregnant with their child, Jennifer, at the time of his departure. The two maintained correspondence, but it was far and fleeting, averaging once a year. Eventually, Caroline fell ill from smallpox and died in 1720, caused by her father's prior infection and his neglect towards medical treatment for her. Edward did not learn of her fate until two years after the fact.
- The dress Caroline wears in her concept art can be seen being worn by her daughter Jennifer, both as a child and a young adult, albeit in different colors.