Laughing Jack, also known as James Gant, was the captain of the gambling casino ship The Lady Luck. He is the brother of Tom and Ava and a servant of the Shadow Lord.
Laughing Jack was born in Plains territory, alongside his siblings Tom and Ava. The three of them had a psychic link that allowed them all to know the thoughts of the other, as if they were of one mind. When they came of age, the siblings split up, with Jack travelling the furthest from his home. His travels brought him in contact with the Shadow Lord, to whom he swore service in exchange for power.
Afterwards, Jack got himself a gambling ship called The Lady Luck, taking on the alias 'James Gant', and hired a crew to work it. They sailed along Deltora's west, cheating people of money and forcing them to row the oars when they could not pay it back. These slaves would then be turned over to the Grey Guards and taken to the Shadowlands. Jack also used his magic to enchant the games room, so that people could not escape until their debt had been paid.
Arrival at Bone Point
About a month before the seven gems were stolen, the Shadow Lord commanded Jack to put out the Bone PointLighthouse. He sought to achieve this by blackmailing the keeper of the light, Red Han. However, Red Han refused to put the light out. Jack kidnapped his daughter, Verity, and promised that she would only be returned when the light was put out.
Jack commanded The Lady Luck to remain docked outside the Light House, and had Verity tied to the prow of the ship so her father could watch her die from exposure. Despite this, not only did Red Han refuse to put out the light, but the seabirds provided Verity with food and water, and all clouds and wind left Bone Point. This essentially stranded the ship, as there were no slaves to row it.
Jack's crew began to grow restless, and suggested freeing Verity to break the curse, but he refused. One day, they attempted a mutiny and tried to free Verity by force, but Jack explained they no longer needed her anyways. By now the Shadow Lord had destroyed the Belt of Deltora and scattered the gems, which meant the ship could return to the River Tor. However, none of the crew were willing to go, as the chances of drowning at the oars was significant. Gant was able to change their minds by promising all the gold he currently owned, and should he take a single piece, he would take to the oars. In exchange, the crew would row the ship until new slaves could be acquired. The crew agreed to the deal (after killing those who did not), and Verity swore to them all that their words would condemn them.
After his crew went to the oars, Jack remained on deck with Verity. She taunted him about his failure at Bone Point, which prompted him to stab her through the heart. As Verity died, the ocean suddenly sprung into a violent storm that struck The Lady Luck, killing all the crew. Jack was only able to survive thanks to the Shadow Lord's intervention.
With his ship gone, Jack became a travelling nomad known as 'Laughing Jack'. He turned Red Han into a black horse, and forced him to pull his new wagon. As a nomad, Jack continued to scam people out of money, and even killed some people when he was not satisfied with the value of their belongings.
Laughing Jack's reputation had earned him the hatred of Steven, who would have killed him long ago if he did not use magic to hide his trail. Also, he came into the possession of Honey, Bella, and Swift after they were separated from Lief, Barda, and Jasmine. Using his magic, he turned them into black horses (or in Swift's case, made her larger) and hitched them to his wagon alongside Red Han.
Under the orders of Kirsten, Laughing Jack waited at the Riverdale Signpost for Zerry , who had stolen the Belt of Deltora from Lief under Fern's instructions. Once he had Zerry, he made his way to The Funnel to dispose of him and the Belt. However, the companions and Steven were able to deduce the code Kirsten used to contact him and Fern, and followed him. Steven distracted Jack while Lief and Jasmine searched for the Belt. He quickly caught on, however, and scrambled to escape — kicking away a sack in the process that held Zerry and the Belt inside. Lief realised this, and called for Steven to help him and Jasmine retrieve the bag before it fell into The Funnel, allowing Jack to get away.
Realising he had failed yet again, Jack tried to escape, but was confronted by the companions. He captured Jasmine and threatened to kill her if Lief or Barda followed him, before offering a deal. If they gave the Belt of Deltora to Ava, he would return Jasmine, then dispose of the Belt and his sister. Lief refused, and Ava warned her brother that she saw death in his future.
At that moment, Jasmine struggled wildly and a bag containing gold from the Dread Gnomes fell in front of him. Jack greedily claimed the gold without a moment hesitation. However, unbeknownst to him, Lief and Barda had been aboard The Lady Luck at Bone Point, and kept a gold coin from it, which Jasmine had hidden inside the bag. By taking the gold, he had broken his oath, and was transported onto the deck of The Lady Luck. He was last seen being dragged below deck by his undead crew, cursed with eternal life as undead beings for their greed.
Jack was a tall, thin man who beared a resemblance to his brother Tom. In his youth, his hair was black, as seen in the vision Lief, Barda, Jasmine and the kin witnessed in the Bone Point Lighthouse. His hair was pushed behind Jack's prominent ears. When Lief and Jasmine first encounter him in flesh, his hair is brown, much thinner, greasy, and tied back in a braid as skinny as a rat's tail. He had hollow, dark eyes. His smile resembled his brother's, Tom's. The second time Lief and his companions encounter him, Jack had disguised himself as his sister Ava, dying his hair dull brown, powdering his face white, wearing her blindfold and dressing in her clothes in order to deceive the companions and give them advice he was sure would lead to their deaths.
Jack is greedy, cunning and deceitful. He manipulates people to get what he wants, preying on the desperate and gullible. When he was the captain of The Lady Luck, he would trick people into far deeper debt than they expected by charging three coins for every one they loaned from him to play his games. Later, when he travelled the land, he used similar tactics, loaning a certain amount and then demanding several times the original sum from his victims. If a clients debt became too great, he would take their lives. He is also a coward, and will sacrifice anything to protect his own skin.
In his youth, Jack and his siblings were linked mind to mind. He rarely made use of this gift after he joined the Shadow Lord, but his thoughts would sometimes reach Tom or Ava without his knowledge. His master also granted him some magic powers, as evidenced by the shutting spell on the door of the gambling room on The Lady Luck, and his ability to transform Red Han into a horse and disguise Honey, Bella and Swift. He also possessed quick reflexes, and was at times described moving like a gangly spider. He was also a skilled conman and assassin as per his main trade on land.
He was also a capable actor, successfully convincing Lief, Barda, and Jasmine that he was Ava.