- “Treachery! Mutiny! I won't stand for it! I'll have you in the dry-dock, Skiff, and take away your sail!”
- ―Sailor John, Sodor's Legend of the Lost Treasure
Sailor John is a pirate that was in the navy for a while, and Skiff's former owner.
Before he was a treasure hunter, Sailor John was in the Navy, but was kicked out for unknown reasons. He then learned of the lost treasure of Captain Calles and travelled to the Island of Sodor, travelling up and down the coast of Arlesburgh, trying to find the treasure, but would leave by dawn so as not to be caught by the police.
After Thomas rediscovered the pirate ship in Calles Cavern, Sailor John converted Skiff to run on rails, meeting Thomas for the first time when Thomas was eavesdropping on him. John initially befriended Thomas and began working with him to find the treasure, but turned against him when they failed to find the treasure, believing Thomas had possibly taken it. When he found out that Sir Topham Hatt planned to donate the treasure to the museum and would be keeping it in a safe in his office at Knapford overnight, Sailor John blew up the office and took the treasure. Skiff did not want any part in the heist, but had no choice in the matter.
Thomas chased Sailor John and Skiff to the top of a hill, where he found that the pirate ship had been taken to the top via unknown means and that Skiff had been tied to it. When Sailor John released Skiff's anchor, the weight of the ship pulled him and Skiff down the hill. Thomas chased Sailor John, Skiff, and the pirate ship through Arlesburgh West, where Rex, Mike and Bert managed to stop the pirate ship by shunting a train of ballast hoppers onto the line and Ryan caught onto a rope tied to the ship, pulling it over. Thomas continued to chase Sailor John and Skiff through Arlesburgh, where John attempted to destroy Thomas by throwing dynamite at him, but Skiff stopped him. Sailor John managed to get out to sea with the treasure chest, but was defeated when Skiff capsized, causing him to lose the treasure. The following morning, the police arrived and Sailor John was subsequently arrested for his crimes. Skiff was then given to Captain Joe.
Kicked out of the navy, Sailor John retired to the Island of Sodor and became obsessed with the idea of finding the lost treasure. He can be quite a charmer, appearing both funny and likeable, but underneath his apparently friendly exterior lurks a ruthless schemer with no true friends apart from Skiff (his sailboat) and loyalty to none but himself. He is smart, energetic and practical, capable of elaborate planning and feats of engineering, such as adapting Skiff for the rails or commandeering the pirate ship and rigging it up as an escape vehicle.
- John Hurt (UK/US)
- Kōichi Sakaguchi (Japan)
- Fred Meijer (The Netherlands)
- Peter Weis (Germany)
- Óscar Gómez (Latin America)
- Gadi Levy (Israel)
- Sailor John is the first human antagonist in the series, excluding P.T. Boomer as he did not make it to the final cut of Thomas and the Magic Railroad. However, John's particularly dark personality and penchant for dynamite are somewhat similar to Boomer's.
- Sailor John refers to himself as "Pirate John" in the Sodor's Legend of the Lost Treasure book after he steals the treasure, but not in the actual special. However, he does say "You've got the wrong pirate!", indicating that he still thinks of himself as a pirate.
- Sailor John is the first antagonist in a special since Diesel 10 in Thomas and the Magic Railroad to not reform at the film's conclusion.
- Sailor John is easily the most dangerous villain in the series, as he goes as far as blowing up Sir Topham Hatt's office, and threatened to destroy Thomas with dynamite during the climactic chase scene.
- Sailor John: Where's my treasure?!
- Thomas: Sir Topham Hatt (The Fat Controller) has it. He's giving it to the museum.
- Sailor John: Museum?! What museum? I haven't been searching all this time to see that treasure end up in a museum! It's for me!
- Skiff: But you always said we were going to give it to the museum!
- Sailor John: (Stamps on Skiff's deck, growling) Oh, get my treasure back, Thomas!
- Thomas: No, Sailor John! That treasure didn't belong to you and it didn't belong to the pirates! It was stolen! So it's going to the museum, and that's the end of it. (Chuffing forwards)
- Sailor John: I will not be pushed aside! Hold firm, Skiff! (Shunted into a siding) Ahh!
- Skiff: Sorry, Thomas!
- Sailor John: (Jumping on Skiff's deck) I WANT MY TREASURE!
Thomas encounters Sailor John at the Coastal Cliffs in Sodor's Legend of the Lost Treasure.