Captain Ishmael Squint is a cruel pirate who sails the Sea of "Jumanji". After Van Pelt, Trader Slick and Professor Ibsen, Squint is the most recurring inhabitant of "Jumanji".
All things considered, Squint is a man of the sea, with an instinct to command other sailors, thanks to his large stature. He is a superstitious man as he almost throws Alkan overboard due to him attacking an Albatross at sea, which Squint insists is an act of bringing bad luck.
Squint's motives change in each of his appearances:
In "Eye of the Sea", he lost his nose during the battle against the one-eyed sea monster with a hideous odor called "The Draken" over 20 years ago. Squint's vengeful pursuit of the Draken is remininscent of Captain Ahab in Moby Dick. The monster ate Squint alive before Alan stabbed it in the eye, killing it.
In "Return of Squint", despite what happened previously, Squint later came back to "Jumanji" with two new shipmates, forcing Judy, Peter and Alan to help him search for treasure at the bottom of the sea with Ibsen's submarine, but get captured by demonic mermaids with his new shipmates while the other three escape.
In "The Ultimate Weapon", despite his past defeats, Squint along with other "Jumanji" residents were invited to Trader Slick's auction for the Trans-Vector, where he was one of the most interested and active members of the auction, but he didn't seem to understand how it worked.
Episodes of Jumanji
In "Eye of the Sea", on a stormy day, Judy and Peter enter "Jumanji" and the two arrive on the shore of a sea where's there's a pirate ship nearby. As Peter goes to board the ship, he was attacked by a giant Lobster. They're saved by Alan who defeats the giant lobster but his sword breaks. The three board the ship and meet the pirate, named Captain Ishmael Squint. He plans to sail to the Eye of "Jumanji", a portal that leads out and he wants Alan, Judy and Peter to be his crew which they agree to after an argument about it. After a day out at sea, Peter gets promoted to First Mate and Alan gets sea sick. Peter immediately takes advantage of his new position to order Alan and Judy around, even placing Alan in the Crow's nest despite him being sea sick. After Alan saves Peter from an Albatross, Squint nearly throws him overboard for defying a forbidding curse but Peter convinces him not to. In the graveyard of ships two massive Electric Eels attack them. Peter and Alan manage to defeat them and Squint changes his mind about Alan. While looking for Squint some time later, Alan and Judy discover in the map that they've been going around in circles in one spot for some time and are confronted by Squint. Squint reveals that what he's really after is the one-eyed sea monster called: The Draken. This is a creature that's bigger than his ship, with intolerable odor, who ate Squint's nose 20 years ago and Squint wants revenge on it. They find the Draken heading towards them and Alan tries to steer the ship away with Judy's help. Squint tries to get Peter to help him, but Peter's loyalty is with Alan and his sister and he helps them. They manage to steer away, but the Draken attacks anyway. It apparently eats Captain Squint and creates a whirlpool to sink the ship. Alan, Peter and Judy climb the Crow's Nest and Alan uses a rope to bungee jump into the Draken's eye and stab it with his broken sword, killing it and causing it to explode.
In "Young Alan", when Judy and Peter travelled back in "Jumanji's" timeline, one of the projected visions they saw was their 1st meeting with Squint.
In "Return of Squint", the two are sucked into the game, finding themselves surrounded by giant Salamanders, but Alan manages to drive them off with a light bomb. Peter got some of the Salamander slime on him without any notice. The three raid Ibsen's lab and steal his submarine, but Peter turns into a salamander. They're unable to find an instruction manual for the sub and are running out of air with Alan unable to figure out how to surface. Judy manages to hit a manual override and they surface near a desert island where Captain Squint and two men are. Captain Squint reveals he survived the Draken attack, although it was a very near thing and ended up washed up on the island. Squint hijacks the sub and plans to use it to find a sunken city full of treasure and forces Alan, Peter and Judy to be his crew again along with his two men. Peter and Judy are forced to serve Squint's men while Alan is forced to help pilot the ship. They get attacked by a giant whale, but Alan drives it off with a torpedo. The pressure gets too much for the sub and Squint refuses to listen to reason, sending Judy and Alan into the back to fix a leak, but the sub breaks in half from the pressure. Alan and Judy get into scuba suits just as the part of the sub breaks completely and find nobody in the front half, but encounter a fully salamander Peter who is free. The demonic shark attacks them, but Peter and Alan manage to drive it off. Peter finds the treasure, but Squint attacks before Peter defeats him. Two demonic mermaids show up, but Peter warns Alan and Judy while Squint and his men fall into the trap and disappeared along with the treasure tower. Alan and Judy collect all the treasure left and find a balloon-like plant that can take them to the surface. They're forced to drop their treasure in order for it to work, because the treasure was too heavy. But they safely make it up, but have to retrieve Peter who turned back into himself. Judy realizes Peter solved the clue: the machine that took them to the deep was Ibsen's sub while what they needed to keep was the ballon plant as it was able to take them back to the surface. Clue solved, the two return home, leaving Alan to swim to the nearby island for coconuts and crabs Squint and his two mates had. At home, Peter is now the best swimmer on the team due to his experiences as a salamander teaching him better swimming techniques.
Despite his previous defeats, Squint reappears in "The Ultimate Weapon", having returned to "Jumanji's" mainland and is invited to Trader Slick's Shop to take part in Slick's auction for the Trans-Vector where "Jumanji's" community of villains united in their common hatred for the trio. Squint claims the Trans-Vector after a chase ensues but Van Pelt forces Squint to hand it over and uses it to casts Alan into the Nightmare World. He tries to do the same to Judy and Peter, but the Trans-Vector is stolen by Ibsen, allowing them to escape.
During the chase to get the Trans-Vector back, Squint tries to get the Trans-Vector and fails, but Peter and Judy manage to jump onto the back of The Judge's vehicle. He tries to cast them into the Nightmare World, but they're saved by Van Pelt and Von Richtor who capture him and accidentally wreck Van Pelt's traction engine, but the Trans-Vector's still in the vehicle. The two ultimately go over a cliff tied to vines, but manage to get the Trans-Vector. As The Judge and Squint try to pull them up, Peter and Judy untie themselves and quickly open a portal to the Nightmare World which they escape through. The vehicle comes through and crushes a creature that was chasing Alan. All that does is give the thing mechanical properties. On the run, Peter manages to align the Trans-Vector and opens a portal back to Jumanji that they escape through. There they encounter Van Pelt, Von Richtor, The Judge and Squint, but Ibsen takes the Trans-Vector and plans to use it to send everyone to the Nightmare World before he destroys it, but Alan knocks it out of his hand with a rock, but it lands so that the portal is still opened and the villains run away and the creature chasing Alan in the Nightmare World comes through. Peter retrieves the Trans-Vector and opens another portal, but the creature struggles not to be pulled in. Judy realizes their clue means they have to toss the Trans-Vector inside the creature's mouth and Peter does so. The Trans-Vector is caught in the mechanical blade inside the things mouth and explodes inside the creature, destroying it.