he episode begins with Ash, Misty, and Tracey riding on Lapras when they are almost run down by a boat owned by a boy named Tad. Misty angrily gets the boy to apologize for almost hitting Togepi. Tad apologizes and proceeds to call Misty "pretty". Tad knows Ash from his victory over Rudy of the Trovita Gym.
On Tad’s boat the gang is told by Tad that he is also trying to get into the "Pokémon League" and that he had been after Ash had battled for his Badge and that Ash had used pure power to win. Misty comments that Ash does not have any skill. Tad challenges Ash to a battle claiming that he likes to challenge people who know what they're doing. Misty, however, jokes about this by pretending not to see Ash while Tad describes him. They then set a course toward Cleopatra Island which they presume to be deserted.
Team Rocket however is on the island fixing up some sort of machine and spot "the twerps". Tad and Ash begin their battle with Ash choosing Pikachu and Tad choosing Poliwrath, this Poliwrath is wearing a golden belt that it won from Tad’s local town for being the “most powerful” Pokémon there. Misty and Tracey are puzzled by this choice but Ash is none the less confident. He orders Pikachu to use Thunderbolt, but Poliwrath immediately uses Double Team to avoid it. Pikachu then uses Quick Attack to get rid of the illusory Poliwrath. As Pikachu gets rid of the last one it uses its tail to shock Poliwrath however despite this Poliwrath seems undamaged. Poliwrath quickly uses Hypnosis followed by Water Gun to defeat Pikachu.
Tracey explains that Tad let Pikachu use its power up so that when Poliwrath used its own power, it can easily defeat Pikachu. Tad cryptically tells the gang that his Poliwrath is at a higher level than Pikachu was. Ash, not very phased by Pikachu’s defeat, tries to match power with power and uses Charizard, much to the shocked of Misty and Tracey. Charizard appears and looks ready to battle. Ash comments that he can handle Charizard but Charizard in turn, like normal, Flamethrowers Ash. Tad notices this and asks Ash if he is sure about the choice, Ash says he is but it proves to be a big mistake as Charizard flies off on its own. Charizard does nothing that Ash tells it and flies around trying to get Poliwrath with a Flamethrower and fails every time. Tad explains to Ash that Charizard may be powerful but he is unable to control it. The match comes to an abrupt end when Poliwrath narrowly misses with its Water Gun on Charizard’s tail and instead unleashes a powerful Ice Beam. It hits Charizard who is locked in a cage of ice all over, save for its tail. Tad recalls Poliwrath but promises Ash a rematch once he learns how to handle Charizard. Tad leaves with Charizard freezing and Ash seething from the defeat. Team Rocket watches the match noting that they know how it feels but they are determined none the less to get Pikachu.
Later that night Ash is up trying to warm up Charizard from the ice cage, by rubbing Charizard’s hide until his hands are literally red and raw. He is helped by Pikachu for a while. Ash tries hard to make sure that Charizard does not freeze and eventually it wakes up. Charizard begins to panic when it notices its tail, and eventually gets knocked out once again. Misty and Tracey, meanwhile, are away for fire wood but come back soon enough and notice the disturbance. Ash and Misty continue to rub Charizard’s back and neck while Tracey checks its temperature. It is still very cold and Tracey gets some fire wood and Misty gets a blanket. Ash notices that his hands are raw. He does not care, however, and continues rubbing, wanting to help Charizard heat up. Charizard once again wakes up and tries a Flamethrower. However, it does not work. Ash tries to get Charizard to calm down, even going as far as to let Charizard use its Flamethrower on him when he's feeling better. Charizard finally surrenders and agrees to let Ash help it unhindered.
Ash talks to Charizard while rubbing, reminiscing that Ash has had Charizard since he was a Charmander and then when it evolved into Charmeleon. Ash admits he's not the best Trainer and makes a lot of mistakes but he's always trying to get better and hopes that one day Charizard and him will battle side by side. Charizard lies there listening to Ash's words and remembers how when it was a Charmander Ash saved its life when it was abandoned in a rainstorm by its Trainer. It then remembers the good times it shared with Ash when it was still a Charmander and then how, despite evolving into Charmeleon and Charizard and growing disobedient Ash because of side-effect problem, but he has still never given up on it. Meanwhile Misty and Tracey have lit up a few more fires and they and Pikachu help to rub Charizard to make him better. This continues all the night.
In the morning Charizard wakes up to find Ash sleeping on him from last night and moves away from him without waking him. Ash and then gang awaken to a roar that comes from Charizard who shows Ash his tail flame which is just as strong as normal. The gang is overjoyed to find that the rubbing worked on the Lizard Pokémon. However, Team Rocket attacks by causing an explosion that lets them trap Pikachu inside a giant drill machine. Tad also notices this and rushes to where the explosion came from. Tad rejoins the group just as Team Rocket says their motto. Pikachu is trapped in a shock proof box making his attacks useless. Team Rocket soon makes their getaway by digging a tunnel. Just as Ash tries to pursue them, Charizard flies alongside Ash and gives him a lift on his back. They fly after Pikachu through the tunnel until they come to the other end near a beach. Charizard uses its feet to grab the machine before it can go any further and pulls it back up the hill. Charizard attempts to burn the drill but Ash stops him to prevent him from burning Pikachu. Instead Charizard crushes the drill with his foot and then bites the box containing Pikachu, destroying it. Pikachu is returned to Ash but Team Rocket is not done yet. They bring out some drill weaponry and attempt to slice Ash, Pikachu and Charizard. Pikachu and Ash are struck down, and seeing his master in danger, Charizard learns Dragon Rage. This attack destroys Team Rocket’s machine and sends them blasting off once again. Tad, Misty and Tracey finally find Ash and his Pokémon. Ash agrees to a rematch with Poliwrath to Charizard.
Back on the beach, Tad sends out Poliwrath while Ash uses Charizard and the battle begins. Poliwrath starts with a Water Gun but Charizard is able to dodge after finally loyality was returned and obeying an order from Ash. It flies around for a few seconds before unleashing an Ember; it sends multiple streams of fire toward Poliwrath. However Poliwrath counters with another Water Gun by spinning on the spot dousing the flames. Seeing an opportunity Charizard tries a Take Down but Poliwrath counters again by catching its leg before it hits. Poliwrath then unleashes another Ice Beam but Charizard successfully evades by flying toward the sky. Poliwrath then tries a Body Slam on Charizard but it misses by Charizard doing a spinning maneuver and Poliwrath is knocked into the air. Charizard carries it up to the sky and then does its dreaded Seismic Toss on Poliwrath, winning the match for Charizard and Ash. Ash hugs Charizard and Tad recalls Poliwrath.
Over the sunset the gang waves goodbye to Tad with Charizard still out of its Poké Ball. Ash jumps into the air claiming that nobody will be able to beat him but accidentally knocks Charizard off balance while it is scratching itself with its leg. Charizard accidentally used a Flamethrower at Ash, but he says not to worry and that he could take the heat as the episode ends.
- This episode uses clips from past episodes to form a montage of Charizard when it was Charmander and then evolved to Charmeleon and again into Charizard.
- This episode is somewhat of turning point for Ash and Charizard. After this episode Charizard became obedient like when it was a Charmander and also won many important battles for Ash later, also Ash admits that he wasn't great trainer and somewhere after this episode he became more mature trainer
- There's an error in this episode: when Charizard is preparing to use Dragon Rage on Team Rocket, Ash is without his jacket and hat. However, when the scene cuts back to him after Team Rocket blasts off, Ash is wearing them.
- The "Who's that Pokémon?" in this episode is caterpie.
- "I'll be glad to have a rematch with you Ash, when you finally learn how to tame that thing."
Tad about Ash and his Charizard.
- "We've been together ever since you were Charmander and then when you evolved into Charmeleon. I just want to be a good enough trainer for you."
Ash to Charizard.