Before he came to Sodor, Sailor John used to be in the navy. However, he was kicked out for unknown reasons, and he moved to Sodor afterwards. For many years he sailed up and down the coast of Arlesburgh in Skiff, his sailboat, trying to find the treasure of Captain Calles.
Sailor John was present near the construction of the Harwick Branch Line after Thomas fell into the cavern and discovered Calles' old ship. Following the discovery of the ship, Sailor John fitted Skiff onto a removable railway chassis, and began searching for the treasure on land. During his first night of searching, he met Thomas when the tank engine was eavesdropping on him, and quickly befriended him when he found out he was the one who had discovered the pirate ship. With Thomas' help, Sailor John managed to find the map to the treasure inside the cavern, but had to leave when the sun was coming out.
Together, Sailor John, Skiff and Thomas worked to try and find the pirate treasure. However, when they could not find the treasure, John immediately became suspicious of Thomas, believing that he had used the map to find the treasure before him. He confronted Thomas on the coastal cliffs, where he discovered that the Fat Controller now had the treasure in his possession and that he would be giving it to the museum. Sailor John demanded to have the treasure, but Thomas crossly shoved him and Skiff aside and left.
That night, Sailor John arrived at Knapford, where he destroyed the Fat Controller's office and the safe protecting the treasure. This woke up a nearby Thomas, who chased after him to try and stop him from getting away. In order to escape, Sailor John rigged the pirate ship as an escape vehicle, but the ship was stopped thanks to the help of the three small engines and Ryan. As they were approaching Arlesburgh, Sailor John tried to destroy Thomas with a stick of dynamite, but Skiff managed to stop him. Thomas tried to derail Skiff at a junction, but accidentally sent him onto a different line, much to John's delight.
Though it seemed as if Sailor John would get away, Thomas realized that his line crossed over Skiff's and ran into him at the crossing, but unfortunately ran into the sea. Sailor John was very close to escaping with the treasure, but the chest was too heavy for Skiff to hold. Skiff pleaded for Sailor John to throw the chest overboard, but he was too stubborn to do so and ended up losing it when Skiff capsized. Sailor John finally gave up, and was arrested for his crimes. (TVS; Sodor's Legend of the Lost Treasure)
Personality and Traits
Sailor John is a cold, greedy, ruthless and abusive man who only cares about obtaining the pirate treasure, no matter what it takes to get it. Though he can appear as a charming and friendly person at the beginning, he will quickly change his demeanour if he thinks that someone is interfering with his plans. He was also quite abusive to Skiff for many years, frequently kicking his face into the water or hitting him even in the presence of others.
Sailor John was prone to violent outbursts, and was not afraid of destroying property or harming innocent individuals. This was shown when he hit Thomas in the face with an oar, nearly came close to killing him and his crew with dynamite and threatening to break Skiff apart if he did not adhere to his orders. He seemed to favour dynamite as his main weapon, using it to destroy the Fat Controller's office and nearly using it on Thomas. He was also a skilled liar, convincing Skiff for years that he was going to give the treasure to the museum rather than keeping it for himself.
Sailor John was quite an elaborate and skilled engineer, and invented and used several different designs to use for his schemes. He managed to adapt Skiff to run on the rails with a removable railway chassis that could spin around, and managed to rig the pirate ship as an escape vehicle by fitting it on a railway flatbed and tying it to Skiff.
Sailor John is depicted as being a tall, elderly caucasian man. His hair is light grey, and he also has a beard of grey stubble. His eyes are blue.
Sailor John's regular attire consists of a white turtleneck underneath a dark blue peacoat, black pants and a pair of black leather boots. He also wears a white cap with a black and gold rim.