The helmsman was once a sailor (likely a pirate) aboard a sailing ship in the 18th century. While sailing of the coast of Isla Tesoro's Hurricane Lagoon in the Caribbean, their ship was beached within the island's Ghostly Grotto. It was here that the helmsman would die in the wreck.
The helmsman's skeleton would remain intact for years to come, doomed to sail through an endless storm for all eternity. It is believed that like so many of the grotto's residents, the helmsman is haunted by the ghost of its mortal self.
The Skeleton Helmsman was designed by Marc Davis and slated to appear in Pirates of the Caribbean since it was being developed as a walk-through wax-museum in Disneyland. The helmsman would appear in the final ride and become one of the staples of the attraction's iconography.
Originally, the helmsman was to have dialogue play for his scene, recorded by Paul Frees, about his braving through the storm. According to this cut dialogue, the ship he was steering contained The Royal Fortune and was headed for the Spanish Main. The Royal Fortune being the name historically given to the ships of pirate Captain Bartholomew Roberts who was featured in old scripts for the Pirates of the Caribbean.
Originally it was represented with an authentic human-skeleton due to the lacking quality of fake skeletons of the day. The original skeletons were eventually phased out for more realistic props however it is noted that parts of the original bones are apparently still present in the current figures.
The helmsman was seen in the Dead Man's Cove sequence where he is seen controlling a helm hence his name on a stormy sea located on Hurricane Lagoon before guests pass through the Crew's Quarters.
In Walt Disney World, the helmsman is found nearby the Talking Skull before guests go over a waterfall and into the golden-age of piracy. When the skull's eyes flash red they are taking a photo of guests in-front of the helmsman which can be obtained after the ride ends. In Disneyland Paris, the helmsman is seen alongside an undead Captain Barbossa who chuckles and slashes at guests at they pass by the beached vessel.
The helmsman is one of the skeleton enemies in the Dead Man's Cove level of this video-game, attacking the player and Black Barty. The helmsman is seen in the cutscene introducing the skeletons and has the difference in adaptation of having a hook-hand.
Originally, the helmsman was to have dialogue play for his scene, recorded by Paul Frees, about his braving through the storm. According to this cut dialogue, the ship he was steering contained the Royal Fortune and was headed for the Spanish Main. The Royal Fortune being the name historically given to the ships of pirate Captain Bartholomew Roberts who was featured in old scripts for the Pirates of the Caribbean.
During development of the original Pirates of the Caribbean before it become a log-flume attraction, the helmsman was named, "Jolly Roger" according to Marc Davis and Walt Disney. However, the helmsman was not given a proper name in recent merchandise inspired by the franchise. "Jolly Roger" would later be the name of the main villain in the discontinued video game Pirates of the Caribbean Online.
It is sometimes theorized he might have been helmsman for the crew of the Wicked Wench due to their appearances as skeletons in the scene proceeding the helmsman's wreck. The truth to this remains a mystery.
The official poster of The Curse of the Black Pearl depicting the helmsman