Olivia was born in Manchester, United Kingdom to Matthew "Apollo" O'malley and Grace Belle Wilde Kenway in June 1727. Her childhood was spent at the family estate in the upper district of Manchester. At the age of 6, her father had begun to train her in combat and by age 8, she was using military-grade crossbows. The following year, on her 9th birthday, Olivia was gifted a hand-crafted sword made especially for her. Only 21/2 years later, she was on her way to becoming her father's protege, a diplomat.
On her 11th birthday, Olivia was forced, along with her mother and father, to leave Britain and move back to their estate in France after Mathieu stepped down from his position of Lord Diplomat of England, at the start of the Paradoxian War. By that time, she had already begun her training as a diplomat and a politician. Her father's friend, Josef Strom, had taken up being her combat mentor continuing the training her father had started with her many years prior. He began training her from a strategical standpoint; taught her how to plan and coordinate attacks, command units and eventually how to command entire armies. At age 15, she had become a princess of Switzerland and moved with her dad and mom to Berne. After only three years, they were on the move again back to France. On her 18th birthday, she was given her very own Kenway family armor set.
2 years passed by after her 18th birthday, and Olivia was on her way to making a mark as a very powerful woman in a man-run world for being the daughter of a highly successful naval strategist and renowned politician. On her 20th birthday, Olivia received a unique crossbow that was quadruple in power to that of a standard swiss military crossbow and triple in power to that of a Norwegian bow. The make was of gold plating and a strong cable. Only a few short months later, her father had ascended to emperorship in the Ottoman Empire and within a few months of her 21st birthday, he fled to France and retook his rightful throne. With only a month to spare before her birthday, her father and her planned an assassination of himself which went smoothly until other world leaders got involved and forced Olivia to step down, but not before she abdicated it to her second cousin Ryan. Shortly after the exchange, she went into hiding.