When we first meet him, Sailor John is on the little Arlesdale Railway near Duck's branch line at the Sodor Dynamite Company. Bert first saw him and he introduced himself to Bert but the little engine had no time to talk to him and left him standing on the track.
Frank then met John and realized that he grumbled too much making the two good friends. He and Sailor John talked almost throughout the rest of the day...
Bert then wondered why Sailor John would be at the Dynamite Company when there is no dynamite to deliver. According to Sailor John, he said a clumsy crane from the Docks came over and knocked the dynamite off!
Bert and Mike had a delivery that day where the bigger engines were there to see them but Bert suspiciously saw Sailor John talking with the horrid lorries by the Brown Turntable, Bert shouted "no!" but Mike thought he said "go!" and the two set off causing an accident where Bert nearly fell off the rails.
Sailor John then ironically popped up and told Sir Topham Hatt that he has help for him on the railway and that help is Lorry 1, Lorry 2 and Lorry 3 who Sir Topham Hatt said were unwelcome to his railway. Duck wondered why the lorries were there, too.
Suspicions were everywhere as it is Sailor John's first day on Sodor and that he probably wasn't leaving any time sooner...
Later on, Sailor John's greediness kept spreading as Bert took Sailor John to the Ulfstead project to investigate the abandoned mine and he brought dynamite with him, as well.
Sailor John arrived at Ulfstead to investigate the problem with the abandoned mine, he told the Pack to cover their ears because the explosion will be loud. He blew up the abandoned mine to see what was inside for himself, inside were rubies, sapphires and golden doubloons blocking the entrance.
John then lies to the Pack that there's nothing in there and goes beside the abandoned mine as the Pack rushed away. Oliver then arrives because he was also said to investigate the abandoned mine but was scared away by Sailor John pretending to be the ghost of Captain Calles, a Sudrian folklore who buried his treasure somewhere on the island.
Sailor John laughs at Oliver's scaredness and tells him to never come back. He stayed behind the abandoned mine for quite awhile making it mysterious for the fact he wasn't doing his job at the dynamite shop.
Later, Logan was tricked by Gordon that there was no coal on Sodor and told him to go to the end of the line on Sodor to find the coal delivery, Logan met John by the abandoned mine and the devious pirate told him he was Captain Calles' ghost and he guards the mine leading Logan away from the Ulfstead project.
One day, Ivo Hugh was taking the Duke and Duchess of Boxford on a trip to the Sodor Zoo to see the animals perform tricks. When arriving, Skiff sails away with Sailor John onboard very speedy and off somewhere. The Duke and Duchess ask about Skiff and Ivo Hugh tells them it is a zebra and wonders why they were in such a hurry!
Ivo Hugh collects all the animals except the zebra which he sees at Ulfstead, he also sees Skiff and Sailor John sneaking into the abandoned mine. John jumps off and runs into the mine mysteriously.
The mystery between Sailor John and Skiff continues to every engine on the Island of Sodor. Logan sees it he overhears the engines talking about Sailor John at Knapford pushing Hector for Duck's goods train. The train was delayed as Duck is taking Sir Topham Hatt to the Arlesdale Railway to have a word with Sailor John.
On the other side of the railway, Duck arrives with Sir Topham Hatt at the Arlesdale Railway to see that Sailor John is not at his usual job at the Dynamite Company. Bert tells them that he hasn't seen Sailor John for a while now and doesn't know what to tell them.
Meanwhile, Logan and Hector investigate the mystery of Sailor John and his railboat, Skiff. He hears them talking as Skiff tells Sailor John that he wants to give rides to the children at Arlesburgh Harbor, Sailor John lies that it was part of the deal.
Logan and Hector are close to hearing more until Bill and Ben ruin the moment by telling him to get out of the way and that they can't be late. Sailor John overhears Bill and Ben and sees Hector watching them and sails away with Skiff.
Later on, Gator is tricked by Lorry 2 to take the presents and the Christmas tree to outside of Ulfstead Castle. When Gator arrives, there is no Sir Topham Hatt there...
Sailor John pops out of the mine where Gator hasn't seen that. He realizes it and asks who he is, Sailor John lies to Gator that he is Captain Calles and that he's here to pick up the presents for Sir Topham Hatt and the Earl. Sailor John tells Gator why they are not here and says that they are entertaining the guests and engines at the Christmas party.
He then lies that he was asked to take the presents out and prepare them for distribution when the time was right. Gator says that sounds okay and Sailor John removes everything from the cars, Gator huffs away to enjoy the party.
When arriving, there are no presents, Christmas tree and decorations at the party. Gator thinks he's ruined Christmas but Sir Topham Hatt tells them that they don't need presents to be happy. Meanwhile, Sailor John and Skiff are enjoying the presents and decorations deep inside the Ulfstead Mine, Skiff tells him that he shouldn't've lied to Lorry 2 but should be enjoying presents with everyone but Sailor John tells him it was miscommunication.
However, once the Christmas storm is gone: Sailor John says that he'll take his attention to opening the Christmas treasure. Sailor John says afterwards everyone will want the treasure knowing it's up for grabs, Sailor John tells Skiff that they are going to be more powerful and rich than Sir Topham Hatt and the two enjoy their Christmas night.
In the fourteenth season, the horrid lorries talk to him about trying to get the trees from Henry and he won't give the trees to them. Sailor John tells them Henry suspects something and tells them they'll need to find their own trees as he needs wood to hold crates for his dynamite. There are some trees in the forest that they won't notice that will be taken away and Sailor John tells them to get on with it as the sun will be rising soon and he doesn't want to be seen by one of Sir Topham Hatt's engines. The lorries rush away and Sailor John leaves with Skiff.
One day, George sees Sailor John and the lorries at the woodshop when stealing wood and immediately after leaving, George tries to tell the engines what he saw but the engines know George is famous for making up stories so no one believes him.
George then tells the lorries to send a message to Sailor John and to meet him later that night. Sailor John does so when he arrives on Bulgy.
Bulgy is back to being a useful double-decker bus again and Sailor John goes to make a deal with George because of no engine believing him, he bribes him by saying he can make him a really useful steamroller again and says that if he ever needs him to come by his usual residence in the abandoned mine at Ulfstead Castle. George accepts the offer thus becoming a member of his crew and Sailor John leaves on Bulgy.
Sailor John is greedy, evil, devious and has a bad attitude, he has a short fuse and grumbles a lot which would explain why Frank talked with him for a long time when he first met him. He's also sneaky and a deal maker as he bribes George into joining his group because he states he will make him a really useful steamroller again.
- In the Spanish version of Keekre24's series, Sailor John is called Maninero Juan.
- In the French version of Keekre24's series, Sailor John is called Marin Jean.
- Season 13: Bert's Arlesdale Fail, The Duke of Hazard (cameo), Rust or Bust (cameo), Oliver’s Fossil Fright, Who Stole The Coal?, Toad Gets Towed, Ivo Hugh's Day at the Zoo (does not speak), Hector and Logan's Hot Pursuit and How Gator Stole Christmas
- Season 14: Millie's Castle Hassle (mentioned), Henry Gets Stumped, Quarry Quest (mentioned), Double-Decker-Wrecker, Furious George, Dirty ‘Arry, James in a Jam, S.C.Ruffey's Sweet Tooth, Flat Stanley and Hatt Trick
- Season 15: Roundhouse Roulette (mentioned), Flash Gordon (mentioned; not named)
- Specials: Saving Pirate Ryan