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Laughing Jack is a villain in the Deltora Quest who is a con artist. He is the brother of Tom and Ava. He was a ruthless and brutal loan shark.
While not much of Laughing Jack is known before he became a servant of the Shadow Lord, it is known that he is the brother of Tom and Ava.
Prior to being known as Laughing Jack, he was once known as James Gant.
He ran a gambling ship known as the Lady Luck. In the event that the players did not have money, he allowed them to borrow money from his casket. Unbeknownst to the players, however, they actually had to pay him back for three times the coins they borrowed from the chest.
Since they inevitably could not pay him back the money they owned, they would be enslaved by him, being forced to row the oars where they ran the risk of drowning. In the event they survived, they would eventually be sent to the Shadowlands.
Eventually, Laughing Jack would be ordered by the Shadow Lord to extinguish the Bone Point Lighthouse. To do so, he scammed Red Han out of dozens of gold coins. That was a debt he could not repay normally.
He demanded that Red Han put out the light as payment, but he refused. So he kidnapped his daughter Verity. He tied her to the figurehead of his ship so that he could watch her die slowly.
Even so, Red Han refused to do so. As the wind stopped blowing, Laughing Jack was unable to leave the lighthouse.
His crew attempted to free Verity, but Laughing Jack refused to let her leave the ship. Since he did not have any slaves at the time, he demanded that his crew row the boat instead.
However, they refused, as they knew from the slaves that had been forced to the oars how dangerous it was. Laughing Jack persuaded them by offering them the gold in his casket. However, the crew were forced to row the boat indefinitely.
Eventually, Laughing Jack decided to murder Verity. However, this was a mistake and he ended up killing his entire crew. The Shadow Lord rescued him, and Jack decided to continue scamming people out of their money, murdering people if he wasn’t satisfied with the possessions he stole from them. He also transformed Red Han into a horse and enslaved him. His scams earned him the hatred of Steven the peddler. Steven almost catches him, but he escapes after attempting to murder a boy while disposing of the Belt of Deltora.
Laughing Jack impersonates Ava in an attempt to get the heroes killed, but they succeed in killing the Sister of the West regardless. Jasmine tricks him into violating his oath, condemning him to be the one rowing the oars of the Lady Luck for eternity.
Along with the Shadow Lord himself, he can be considered to be one of the nastiest villains Lief and his friends had ever faced.
Like Thaegan, He happens to be a sorcerer who serves the Shadow Lord. However, unlike Thaegan, who cared for her children, Laughing Jack did not care for his crew and enslaved them when they attempted a mutiny.