Pokémon Double Trouble (Japanese: タッグバトル！さいごのジム！！Tag Battle! The Final Gym!!) is the 108th episode of the Pokémon anime. It was first broadcast in Japan on August 12, 1999 and in the United States on September 9, 2000.
Ash is anxious to square off against the Gym Leader who holds the final badge of the Orange League. But then he learns that this Gym Leader is none other than the kindly townswoman who just helped him rally against a Team Rocket sneak attack.
Ash and his friends arrive at Kumquat Island for Ash's fourth and final Orange Crewbattle. As they are walking on the beach, a woman rushes in and abruptly hugs Ash. She then realizes what is happening and apologizes, saying that she mistook Ash for her son Travis, who had, like Ash, started a Pokémon journey with a Pikachu. Just then, the beach is attacked by Team Rocket's Robo-Rhydon, driven by Arbok and Lickitung and weaponized by Weezing. Jessie tells Weezing to use Hyper Beam, but it instead uses Smog, to her disappointment. Nevertheless, the attack still causes beach-goers to flee in a panic.
Ash decides to stop Team Rocket, but Jessie has Arbok use Poison Sting on Ash and Pikachu. However, the woman has her Alakazam use Reflect to block the attack. She scolds Team Rocket, warning them to never return. Alakazam uses its Psychic to seal the mechanical Rhydon's mouth shut while another Smog attack is fired, subsequently filling Team Rocket's control cabin with smog. Ash sends out Charizard, who uses Take Down on the robot. In the confusion, James inadvertently presses one of the buttons, causing Arbok to use Acid, which tears a hole in the Rhydon robot. Charizard responds with Flamethrower, which overloads the robot's machinery, causing it to explode and send Team Rocket flying.
The woman introduces herself as Luana, the final member of the Orange Crew, and a local hotelier whose hotel includes a workout Gym and an indoor Pokémon stadium. Ash and his friends are invited to stay in her hotel's most exquisite suite free of charge, and they agree on a Double Battle, to be held the next day, for the final Orange League Badge. In the match, both leader and challenger will use two Pokémon simultaneously, and the match ends when the first Pokémon is unable to battle, wherein the opposing team are declared the winners. While in the hotel's hot spring, Ash and Tracey discuss strategies. Ash is committed to have Pikachu battle, but Tracey surmises that Alakazam will battle. Lacking any Ghost or Bug types that could deal an effective blow, Ash ponders who else could stand up to Alakazam's power.
The next day, the battle begins, with Luana sending out Alakazam and Marowak against Pikachu and Charizard. However, it is revealed that before the match began, Pikachu and Charizard developed a grudge with one another following an innocuous stomp by Charizard that knocked Pikachu over. Sheldon calls for the match to begin and Pikachu rushes towards his opponents. However, Charizard's Flamethrower manages to hit Pikachu, burning the Mouse Pokémon's tail. Ash commands Charizard try to use Tackle on Alakazam. However, Alakazam's Psychic stops Charizard midair. As a result, Ash commands Pikachu to use Thunder Shock, but the attack hits Charizard instead. Ash scolds Pikachu, but the small Pokemon shrugs at his concerns.
After momentarily watching on as Charizard takes successive Bonemerang and Psychic attacks, Pikachu Thunder Shocks Alakazam, freeing Charizard from its Psychic. Luana has Marowak use Body Slam on Pikachu, but Charizard manages to catch Pikachu with its wing. With the two now willing to cooperate, Charizard flies with Pikachu on its back, allowing Pikachu to use Thunderbolt on Marowak, disrupting its concentration. Meanwhile, Charizard continues to fly towards Alakazam, who prepares to land a Hyper Beam at point-blank range. When Charizard pulls up at the last minute, Alakazam is hit with Marowak's wayward Bonemerang attack, sending it and the charged Hyper Beam backwards. Much to Luana's shock, the Hyper Beam hits Marowak. Sheldon checks the two Pokémon and reveals they have been knocked out, earning Ash the victory.
After Ash receives the Jade Star Badge for the victory, Luana tells Ash that he is finally able to compete in the Orange League against the Orange Crew Supreme Gym Leader for the Winner's Trophy. Leaving Kumquat Island, Luana tells Ash that if he encounters Travis, he should deliver him a warm message from home. Ash and his friends sail away on Lapras's back, waving to Luana and her hotel staff. Elsewhere, Team Rocket's cries for help remain unanswered and they are forced to wait out at sea on the remains of their Robo-Rhydon.
This episode has the first Double Battle in the anime, if the battles with Jessie and James are excluded. However, it should be noted that this battle ends when either one of the Trainer's Pokémon faints as opposed to future Double Battles when both Pokémon would need to be knocked out to earn the win.
This is the first of two episodes that featured Tracey without his headband on.
This is the first episode to have a referee in a Gym battle. Almost every Gym battle has a referee from this point on.
Although James reveals that he had intended to teach his WeezingHyper Beam, he never does get around to actually teaching it.
After Luana reveals her status as Gym Leader in the English dub, Jessie comments "I don't care if you're in the Orange Crew or the Grapefruit League", quite possibly a stealth reference to Major League Baseball's Spring Training league in Florida.
This is the second episode in which Ash is mistaken for a woman's son, the first being Hypno's Naptime.
Before the characters enter the Gym, Luana moves her mouth as if speaking but doesn't actually say anything.