As Ash heads back to Hearthome City for his long-delayed Gym battle, he's concerned about his own Gligar's battle woes. Even though Ash gives Gligar lots of special training, it just can't get its act together. Gligar finally gives up and flies away, only to run into Gary Oak. Gary offers to help with Gligar's problem, starting by having a friendly battle between Gligar and Gary's Umbreon. Once the battle starts, Gligar panics, and Gary realizes what the problem is: Gligar is overcome by fear whenever it tries to fight.
Gary thinks Gligar should use a Razor Fang to evolve into Gliscor, and Gary just happens to have a Razor Fang he can give to Ash. Once Gligar is a powerful Gliscor, its fear will be a thing of the past! Gligar loves this idea, but Ash says no; he wants Gligar to conquer its fear before it evolves. Poor Gligar gets another shock when Team Rocket springs an ambush with their giant Gliscorbot, snatching Gligar and making a getaway. Ash manages to leap onto the Gliscorbot before it escapes, but that just means Ash and Gligar end up stuck in the same cage!
While Team Rocket celebrates their catch by eating themselves into a stupor, Ash coaches Gligar to break them out of the cage with X-Scissor. With Gligar's help, the two of them then escape across a chasm, and Gligar's confidence begins to build. Just in time, too, because Team Rocket has caught up with their escaped captives! Ash tosses Gligar the Razor Fang and it evolves just in time to save them both from Team Rocket's clutches. In fact, by the time Gary and the others catch up to Ash, Gliscor has Team Rocket pretty well beat! Gary says his farewells and our heroes get back on the road to Hearthome City, now accompanied by a confident new Gliscor!
While the the group and their Pokémon are enjoying lunch, Ash notices Gligar is nowhere to be found. He stands up and calls out to the missing Pokémon, and Gligar replies by flying out to its Trainer out of affection. Ash wonders where Gligar went to, and Gligar shows off its developing X-Scissor technique. Ash is impressed, and Brock wonders if maybe it's trying to get stronger after being defeated by Paul's Gliscor. Remembering the loss upsets Gligar's feelings, so Ash offers to do some training together soon.
After the group finish their meal, Ash pits Gligar against Buizel. Gligar's confidence starts to waver after Buizel sneers at it, but Ash tells it that everything will be fine. Gligar is satisfied by this, and starts off with an X-Scissor. Buizel expertly dodges before approaching with an Aqua Jet, however Gligar becomes petrified and leaps onto Ash for protection. Buizel continues its momentum and smashes straight into Ash, who is far from impressed. Ash irritatedly asks Gligar what's wrong with it, causing Gligar to get discouraged. Dawn tells Ash that he's going about it the wrong way. She kneels down to Gligar's level and comforts it with a hug. Ash says that he doesn't want Gligar to get spoiled from being treated that way, but Brock notes that being so harsh on it won't get him anywhere, either. He calls on Turtwig to take on Gligar. While Gligar manages to dodge Turtwig's Energy Ball, it does so because it was trying to run away. As it soars into the air, Ash orders Gligar to use Steel Wing, which it does, but falters when Turtwig stares at it ferociously, ready to defend. Gligar then spins around and knocking over Ash again with its weight. Ash scolds the Pokémon, saying that it has to toughening up and stop crying. Gligar takes it a little too harshly, and it flies away sobbing. Watching all of this happen from nearby bushes is Team Rocket,who spot an opportunity to steal Gligar for the Boss, now that it's all alone and defenseless.
Later, Staravia leads the group to a forest clearing, where they find Gligar along with a familiar face: Ash's old rival turned Pokémon Researcher, Gary Oak. The two greet each other, and Dawn is instantly awe-struck by seeing the poetry guy's grandson again. Ash asks Gary what he's doing here, and he explains that he was on his way to Lake Valor to check out the Legendary Pokémon that Ash saw earlier, because Professor Rowan asked that he do so. Gary asks about Gligar, to which Ash replies that it is his. Gary makes a guess that they were in the middle of training when it ran off. Ash takes the bait and gets offended by his assumption, to which Gary clarifies that he was only offering to help him. Ash refuses his offer and tries to call Gligar back to him, but Gligar recoils in fright and hides behind Gary. Ash then grabs ahold of Gligar, trying to pull it away, but Gligar refuses to budge and continues cowering. Dawn and Brock suggests to Ash that maybe he should let Gary help him with Gligar's training. Gary agrees, and Ash grits his teeth in frustration.
Not soon after, the two begin a battle, Umbreon versus Gligar, to try to figure out why Gligar is having problems training. Ash has Gligar take to the skies and dive down for a Steel Wing. Gary calls for Umbreon to use its Shadow Ball. While the attack misses its target, Gligar recoils in fear anyway, and it falls back down and lands on Ash. Gary takes note that Gligar easily gets frightened when facing an opponent. Gary says that the first step they have to take is to try and overcome that fear. Ash pipes up and says that you just have to focus and concentrate, to which Gary quickly shuts him down, saying that he'll never change. He then says that to use Steel Wing effectively, the Pokémon using it needs to jump up in the air as high as possible beforehand, and if they can work on that then Gligar's confidence would surely return. Dawn is amazed by how Gary explained it, to which Ash takes offense. Taking in the feedback, Gligar starts warming up to the battle by bouncing on its tail like a spring, before jumping up to fly. However, once in the air, Gligar becomes scared by the altitude and falls back down to the ground, landing on Ash again.
At that, Gary says that they've definitely got a problem on their hands if Gligar is afraid of heights, too. He then asks how much battling Gligar has actually done, and Dawn explains to him that it's not very much, as Gligar got beaten pretty badly by Paul's Gliscor. Gary thinks on it for a moment before pulling out a Razor Fang from his pocket. He hands it to Ash, telling him the Razor Fang will make Gligar evolve into Gliscor, and if they evolve it, it'll feel a lot better about its abilities. Gligar excitedly tries to grab the item from Ash's hand but Ash stops it, pulling his hand away from the over-eager Pokémon. He tells it that evolution is no substitute for hard work, and that it can evolve after it conquers its fear.
Suddenly, a large noise is heard from nearby and Team Rocket emerges from the trees in a Gliscor-shaped balloon. Gary isn't impressed to see Team Rocket again, who he regards as lame, which annoys the trio to no end. In retaliation to those words, they release the tail spike of the Gliscor balloon and snatch Gligar away. Ash grabs ahold of Gligar before calling out Staravia for help. Jessie sends out Seviper to use Haze and Yanmega to use Silver Wind, knocking Staravia to the ground and allowing Team Rocket to make their getaway. Team Rocket keep Ash and Gligar caged up while they celebrate their victory with a mountain of tinned food. Meanwhile, Gary confidently leads Dawn and the others through the mountainous terrain as the evening wears on.
Later that night, Team Rocket are sound asleep, which Ash tells Gligar is their chance to escape. Gligar nods, and Ash tells it to use X-Scissor to break open the bars on the cage. Gligar's two attempts aren't strong enough, so Ash tries to smash open the cage himself. Gligar watches this in amazement before resolving itself to use X-Scissor again. This time Ash notices a change in the strength of the bar, as it appears wobbly at the top. At this, Ash and Gligar work together and attack the cage bars at the same time, which breaks them open. The two then escape from Team Rocket. On the way they come across an old, rickety bridge, and Gligar jumps on Ash's back as they try to get across it. The bridge's supporting rope snaps, sending Gligar and Ash plummeting. Luckily Ash manages to grab hold of the rope and pulls himself and Gligar up to safety.
Ash looks around for another way to cross the chasm, and notices a tree near the edge of the cliff. At this, he has Gligar knock it over with Steel Wing, and on its second attempt Gligar fells the tree to make a crossing. Ash is proud of Gligar, and tells it that it's earned the Razor Fang that Gary gave him before. Gligar is overwhelmed with happiness and hugs Ash, but the happy moment is interrupted by Team Rocket who appear in their Gliscor balloon who are determined to deliver Gligar to Giovanni. The Gliscor tail shoots out again, but Ash jumps in the way of it and is captured instead. Holding Gligar in his arms, he tells it that he's going to let it go so it can escape. He then does so, and Gligar falls down below. Ash then falls himself while trying to scale the mecha. Ash passes Gligar as they both descend. He then throws Gligar the Razor Fang, which Gligar catches, causing it to instantly evolve into Gliscor. Gliscor is now a lot faster than before and manages to catch Ash, using its tail to cushion their landing. Ash thanks his new Gliscor for saving him. Team Rocket are also impressed to see the newly evolved Gliscor.
Ash tells Team Rocket that Gliscor belongs to him and isn't going anywhere. He has Gliscor use X-Scissor, which smashes into the Gliscor balloon tail and knocks it back. At this, Gary, Dawn and Brock run onto the scene and call out to Ash. Dawn is amazed to see that Gligar has evolved, and Brock congratulates it for doing so. Team Rocket then shout out to the group below angry at being ignored, and Meowth sends out the claws of the Gliscor balloon mecha. This is deflected once again by the real Gliscor's X-Scissor attack. Ash then tells it to grab a hold of a tree branch and charge up its power, which it does, before flinging itself from the tree and using Steel Wing aimed at Team Rocket. James smirks, saying that Gliscor can't beat their mecha balloon's power. Meowth then activates the balloon's Steel Wing mode. Though Ash's Gliscor wins out, and Team Rocket's mecha is split in half. Ash then tells Pikachu to use Thunderbolt, which causes the Gliscor bot to explode and sending Team Rocket blasting off. As the sun rises, Ash and Gliscor exchange smiles, with the rift between them healed and a stronger friendship than before.
Afterwards, Ash thanks Gary for his help, though Gary admits it was really Ash who was the hero. Brock hopes Gary will see that Legendary Pokémon at Lake Valor. Gary casually replies, but accidentally rhymes his sentence in the process, causing Dawn to suddenly freak out and remarks that's to be expected since he's the grandson of a poet. Gary chuckles and follows it up with another poem, and on that note Gary leaves for Lake Valor while the group continues towards Hearthome City.