Jacoby was once a notorious pirate bombardier cursed to live as a skeleton for his part in the theft of Aztec gold. Jacoby served under Captain Barbossa aboard the infamous Black Pearl. After Will Turner sealed a grenade in Jacoby's chest and his body exploded, he prayed to the Aztec gods, who in a strange moment of charity allowed him to keep his skeletal form when the curse was lifted. After some time, Jacoby's scattered remains were washed ashore in a strange land where The Logging Company was in the middle of a massive deforestation project.

In need of a demolition's expert, The Logging Company quickly hired Jacoby as a lumberjack skeleton. Now Jacoby is a crucial member of the company where he puts his skills to use felling trees with explosive efficiency. He also enjoys playing Blood Bowl with his coworkers, where his knowledge of explosives and cunning tactics make him a valuable asset on the pitch. Despite his grim appearance, Jacoby is known for his cheerful demeanor and his ability to make explosive plays that often lead his team to victory.