Arc 2Chapters 26–50
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Gary and Lorelei spent a day at a private amusement park before Gary caught a Psyduck that could use telepathy. The chapter ended with Psyduck willingly entering Gary’s Poké Ball.
Gary received Lorelei’s Ice-type training notes and exchanged an Ice Gem with her before heading to the Vermilion Gym. After resolving a confrontation with the Gym’s doormen, he began his three-on-three challenge against Lt. Surge, with Nidoking facing Electabuzz.
Gary faced Lt. Surge at the Vermilion Gym and won the first two rounds with Nidoking and Rhydon. He sent out Psyduck against Lt. Surge’s final Pokémon, Voltorb, leaving Psyduck’s performance undecided.
Gary defeated Lt. Surge at the Vermilion Gym after Psyduck used overwhelming psychic power to stop Voltorb’s attacks. Lt. Surge awarded Gary the orange Badge, and Gary stayed overnight in Vermilion City before planning to leave the next day.
Gary was tasked with welcoming Caitlin, Unova’s fourteen-year-old Elite Four member, to Kanto and agreed after Professor Oak promised him Dragonite breeding and training resources. At Vermilion Harbor, Lance arrived, confirmed Gary would host Caitlin until their Indigo Plateau match, and offered to cover the expenses with his card.
Gary welcomed Caitlin to Kanto ahead of their exhibition match and showed her around Vermilion City. Their walk ended with the two of them sharing the only available Champion Suite.
Gary and Caitlin shared a hotel suite, where Caitlin’s psychic examination helped Psyduck overcome his evolution bottleneck and become Golduck. After her Pokémon nearly attacked Gary, his cooking won them over, and Caitlin decided to travel with him for the month.
Gary and Caitlin traveled by ferry toward Saffron City, stopping at Porta Vista to enjoy the beach and eat at the Sea Cottage. Caitlin recognized that the restaurant had drugged their food, and the pair pretended to fall asleep as the shady staff prepared to act.
Gary and Caitlin confronted Team Rocket’s murderous gang at the Sea Cottage, where Caitlin killed the attackers and Gary called Officer Jenny. After they returned safely to the Shelly, Agatha proposed a League crackdown that would bring a major assault against Giovanni’s Team Rocket before the Indigo League.
Gary and Caitlin explored Lavender Town’s Spirit Tower, where they outsmarted a trio of mischievous Ghost-type Pokémon. After feeding the ghosts and earning their trust, Gary asked them to take the pair to their Secret Base, leaving them heading downstairs to play.
Gary and Caitlin caught Ghost-type Pokémon in Lavender Town, then reached Saffron City after Caitlin confronted Sabrina’s psychic doll. They settled into a hotel for the night, while Sabrina eagerly anticipated meeting Caitlin.
Gary and Caitlin went to challenge the Saffron Gym, where Caitlin’s power and Gary’s words forced Sabrina’s estranged father to reconsider how he had treated his daughter. The man resolved to return home and face Sabrina.
Gary visited Saffron Gym with Caitlin, where her meeting with Sabrina turned into an instant friendship before Gary received the Marsh Badge in a brief battle. Agatha and Lorelei supervised, then left Gary contemplating his feelings and future with Lorelei.
After reconciling with Sabrina’s family, Gary and Caitlin left Saffron City for Celadon City, with Professor Oak urging Gary to hurry and updating him on Dragonite’s egg. They stopped five kilometers from Celadon to eat, where a group of Mankey suddenly appeared.
At Rainbow University, Erika defended Professor Oak’s achievements after Yuto Sayo insulted him and vowed to expose him. Gary arrived with Caitlin to an exuberant welcome and agreed to give two public lectures, while Chancellor Monet promised to provide whatever equipment he needed.
Gary settled into his new professor’s office at Rainbow University and prepared for an academic exchange by ordering items for possible Pokémon evolutions. He arranged a practical Gym battle with Erika for that afternoon, while graduate students began preparing his Pokémon.
Gary had his Pokémon assessed and assigned to specialized training at Rainbow University before heading to a tutorial match. There, he confronted Yuto Sayo for taking over the arena and insulting his qualifications, then accepted her challenge after asserting his authority.
Gary defeated Sento's Graveler with Eevee and advised Sento to earn eight Badges on a journey before seeking reinstatement. He then prepared a Gym demonstration battle for Rainbow University's students, just as Professor Rowan's Sinnoh delegation arrived and Caitlin reunited with Cynthia.
Gary used a battle demonstration against Erika to teach Rainbow University students about Gym battles, type matchups, and tactical choices, then defeated her Tangela with Scyther. After reviewing the match, he began preparing for the second round.
Gary defeated Erika’s Weepinbell and Gloom in a Gym demonstration match while teaching the students about battle tactics and preparation. Erika conceded the match and gave Gary the Badge, then declined an invitation to the evening dinner.
After waking from a drunken night, Gary learned that Nidorina and Growlithe had evolved into Nidoqueen and Arcanine, while Scyther and Rhydon received Evolution items. He got Principal Monet’s permission to take Pokémon resources from the university’s Breeding Park and invited Caitlin and Cynthia to go with him.
Gary joined Caitlin and Cynthia on a visit to Rainbow University's Pokémon Day Care, where he sought promising Pokémon and arranged to study new evolution links. The group headed to the habitats so Gary could choose Gligar and Sneasel, while Director Robert offered Onix and Poliwhirl ready to evolve.
Gary visited Rainbow University’s Pokémon habitats and chose a mischievous Gligar and a deceptively clever Sneasel as his Pokémon. After securing both, he left with Cynthia and Caitlin to get food before the seminar.
Gary presented his research on the branches of Pokémon evolution at Rainbow University’s exchange conference, demonstrating several newly documented evolutions. He began another demonstration involving Slowpoke and Shellder as the Sinnoh scholars watched in astonishment.
After leaving Rainbow University with research rewards and a stronger team, Gary headed to Erika’s perfume shop, where he encountered Ash and Brock. At the Celadon Gym, he discovered Ash disguised as a girl in an attempt to get a battle with Erika.