In 1718, Hornigold's Benjamin and Edward Thatch's Queen Anne's Revenge attacked a British Man O' War in order to obtain medicines for the settlement at Nassau. During the engagement, Benjamin was severely damaged and forced to withdraw.
One year later, the newly Templar affiliated Hornigold tracked Edward Kenway in an attempt to locate the Observatory. Though she managed to lure Kenway into an ambush of Royal Navy ships, Kenway's Jackdaw sank them all and severely damaged the Benjamin. Lost in the fog and taking on water, the schooner ran aground on the Santanillas islands and Hornigold was assassinated by his former protégé.
- The Benjamin was extremely powerful for a schooner, being more akin to a frigate in terms of damage that it could deal and take.
- During the memory "This Old Cove", Mary Read departed the Great Inagua on a vessel identical to the Benjamin.
- After the memory with Hornigold's assassination, the Benjamin will oddly disappear from the island if the player returns in free roam.