Ash and co are now walking through a very deep and rocky canyon. They soon exit to the edge of a cliff and look down upon a very pleasant city below. Max checks the Pokenav and says this is Crossgate Town. Ash and co admire it and Brock explains that it is the town of winds. May says he's right as a wind blows soothingly on them.

She then notices a Swablu flying above with a weird ring in its mouth. May and Max adore it, but suddenly a large breeze picks up causing the poor Pokemon to fall from the sky. Ash thinks fast and releases Taillow who quickly braves the wind and catches Swablu on its back. It then flies back up to Ash and co. Ash thanks it and seconds later a boy wearing a yellow shirt and sporting the same hairstyle as Swablu comes rushing up. He calls for Swablu and it flies happily into his arms.

Ash tells the boy that his Swablu is really cool and the boy thanks him. He introduces himself as Kaito and Ash and his friends then introduce themselves. After they are acquainted, the boy pulls out another odd ring and tells Swablu they need to train some more. Max asks what the ring is and the boy explains that it is a Pokering.

The boy takes the group into a field where a bunch of hot air balloons are soaring above. He explains that each year, Crossgate City has a Pokering competition in which a ring is suspended on a balloon. The competition is then separated into four groups of four in which each trainer has their flying Pokemon race to retrieve the ring while keeping the others at bay. The first one to snatch the ring and bring it to the goal wins. As he explains it, the group watches a Wingull snag a ring from the balloon as a Crobat and Skarmory give chase. It makes it to the goal and tosses the ring, winning the practice round.

Ash is enticed by this and Kaito explains that the competition is scheduled for today. Brock says it would be great training for Taillow and Ash agrees, but is disappointed that he wasn't here to sign up. Kaito then says he is in luck as the competition is still accepting contenders! May is excited to try out Beautifly as well so Ash and she decide to enter.

The group is next seen in a giant canyon surrounded by bleacher seats. A scoreboard begins post the contenders on the screen. Kaito explains to Max and Brock about the groupings while they wait. He seems confident but Max isn't so sure Swablu can win. Kaito laughs nervously saying this is actually his first competition. Ash and co are shocked but Kaito explains that with his training and Swablu's skill they have the right combination to win. He then wishes Ash and May luck who second the notion to him.

Meowth and Jessie sit on the edge of a cliff overlooking the canyon. They don't see what the big fuss over snatching a ring is, but James enters the scene explaining that it is actually a very important competition. He goes on about how he used to train for the Pokering competition as a boy, and it was very difficult. He says his old teacher made him where strength increasing gear so that he would be in shape for it. Suddenly, he notices an old man with a Crobat on the scoreboard and tells the two that he is his old teacher.

Meowth and Jessie still don't see what the big deal is, but James begins to yell. He says he is going to enter the competition and show them how great he is. The two just laugh and he begins to go ablaze exclaiming that Crossgate City will see what a true Pokering competitor is like. Jessie and Meowth watch the flaming James with embarrassment.

The contestants are now all situated on a platform in the middle of the canyon while the announcer says the grouping will commence. A screen on the A Block begins to shuffle the trainers. Kaito and his Swablu are put into this group along with a girl and her Yanma, a boy and his Wingull, and a boy with a Pelipper. May takes a breath of relief. She seems to be quite nervous.

The B Block then shuffles trainers as well. Ash and Taillow are in this one along with a fat cowboy named Volt who was last year's champion. He is complete with a Volbeat and a toothpick. The other two trainers are a boy and a Ninjask and another with a Golbat. Max and Brock are shocked that he is up against the defending champion on the first round, but Ash is actually excited.

Volt overhears his confidence and says he doesn't stand a chance. Ash and he begin to argue until Volt tips his hat and walks away. May thinks he is very rude. Suddenly, the two are interrupted by James entering the stage. He begins to go on and on about how great he is until Ash and May notice it's him. Kaito wonders if he's a friend of there's, but they deny it. James then says that he is not from Team Rocket today; today he is James the Pokering Competitor. At this, he removes his rocket outfit to reveal a pilot outfit underneath. May is completely ignoring him to watch the C Block shuffle. He whines a bit wanting attention.

The shuffle ends with May and Beautifly, James with Jessie's Dustox, a boy with a Crobat, and a girl with her Jumpluff. Ash and May are shocked by this. James, however, wishes May luck and holds out his hand, but she ignores him again and seems confident now. The D Block is never shown being shuffled.

A hatch opens on the arena floor and a balloon comes out. It rises into the sky with the ring hanging just below it. The A Block contestants then rise from their bunkers each in hot air balloons matching the Pokemon they are using. The announcer issues the start and Kaito releases Swablu. The others release their Pokemon and each one flies in for the ring. Pelipper launches a water gun but Swablu flies right through it. The force of it breaking through the water gun pushes Pelipper back.

Yanma then tries to use swift on Swablu but it dodges. Kaito tells his Pokemon to go for the ring, but he then feels the winds changing. He tells it to stop and pull up. It does so and the other three head towards the ring. The winds then pick up blowing the three away from the ring. Ash and co are shocked that Kaito uses the weather patterns to his advantage. Swablu then pulls the ring from the balloon and Kaito orders it to race to the goal. It does so and tosses it onto the latch, giving Kaito the win for round 1.

The audience begins to cheer as his picture appears on the scoreboard. Ash and co clap as well. Swablu then lands in Kaito's balloon and he congratulates it. Up next is the B Block. Volt seems pretty confident in his balloon but Ash does as well. The announcer declares the start and each trainer calls out his Pokemon. Volt waits a bit and then calls out his Volbeat. He knows he has the advantage with Volbeat's electrical attacks.

Volbeat tries to thunderbolt Taillow, but it dodges and the attack strikes Ninjask and Golbat. Both Pokemon fall smoking to the ground when the attack stops. Max is now worried since Taillow is weak against electricity. Brock also shares his nervousness. Ash orders his Pokemon to the ring and it jets towards it. Volt orders Volbeat to shock it and it does so. Everyone is extremely worried but Ash tells Taillow to break free. It bursts forward using its wings to escape as Volbeat looks on stunned.

Kaito is a little worried but May informs him that Taillow and Ash are a great team. Taillow goes for the ring and grabs it with its beak. Ash then tells it to bring the ring to the goal and it speeds down towards it. Volbeat catches up and uses thunderbolt. Taillow dodges but drops the ring as it does. Volbeat grabs the ring in its mouth but is smacked away by a wing attack from Taillow. Taillow then reclaims the ring and tosses it on the goal for a win.

The crowd goes wild and Ash's picture appears on the scoreboard. Max hops up in down from the stands and Brock is impressed. Taillow flies up to Ash and he congratulates it. Volt looks on stunned at his loss. Volbeat also looks extremely disappointed.

Next up is the C Block contestants. May hopes Ash will see her win and James hopes Jessie and Meowth are watching so he can show them how wrong they were. The trainers all release their Pokemon and they quickly head for the ring. Dustox makes it there first and grabs the ring. May then orders a gust and Beautifly blows the other two Pokemon back. Dustox dodges and flies down; placing the ring onto the goal. May is stunned for a second. She had severely overestimated James and that accounted for her loss. Even Beautifly is stunned.

James's picture appears on the scoreboard and the crowd cheers. Dustox flies to him and James gives the peace sign to May who just stares dumbfounded. Beautifly seems disappointed. Kaito remarks that James is a major competitor and Ash is now set on defeating him.

Outside of the arena, Jessie attracts a crowd by showing off her rare Wingull. It is actually just Meowth in disguise. Trainers begin to offer trades and Jessie grins. She then whispers to Meowth saying they could get a goldmine of Pokemon from this and he laughs. Back inside, the winners from each round are posted. The remaining contestants are then shuffled again and the first round stops as Ash vs. the winner of the fourth round; a boy and his Skarmory.

Kaito wishes Ash luck in his bunker as he boards his balloon. Ash says he'll try his best and he then wishes Kaito luck in his match. The scene then shifts to the match. Skarmory has the ring and is making it to the goal, but Taillow comes in fast; smashing into Skarmory and gaining control of the ring. It flies down to the goal and tosses it on; giving Ash the win. Ash makes a fist of confidence as Taillow happily flies back to his balloon.

The semifinal match is now James vs. Kaito. It is now very cloudy and Brock thinks this could be tough. May just wonders how Kaito will fare against James. The match starts when the balloon begins to rise with the wind. Swablu and Dustox both jet up trying to reach it. Kaito tells Swablu to get the ring and James orders Dustox to stop it. He then notices that the clouds are moving and commands Dustox to stop. It does so and the sun emerges from the behind the clouds; blinding Swablu before it grabs the ring.

Dustox then takes this moment to fly in and tackle Swablu away. It then turns back; grabbing the ring and throws it onto the goal giving James the win! The crowd screams in excitement again as the scoreboard declares him the winner. James and Dustox now seem extremely confident and he declares that his victory is at hand. Kaito cradles Swablu assuring it that it did a great a job. He then hopes to himself that Ash will beat James. James taunts Ash as his balloon returns to his bunker; making Ash even more determined to win.

Jesse and Meowth are now behind their stand with many Pokemon in a net. They gloat on their capture and then decide to go see how James is faring. The finalists' balloons rise up as each prepares themselves for victory. James then notices Meowth in the stands below waving some flags. Meowth is trying to signal to James that he can help him win the old fashioned way (cheating). James is very annoyed by this and waves some flags back; telling Meowth to shove off. The two argue back and forth with the flag signals until James declines the offer and chucks a flag at Meowth.

The announcer signals the start and both trainers call out their Pokemon. They both rush for the ring but James gains a quick lead by having Dustox psybeam Taillow away. Ash's friends are worried now and tell Taillow to do something. Ash orders it to get out of there and it breaks out using its wings. Taillow then goes in slicing into Dustox with a wing attack. It then flies towards the ring with Dustox close behind.

The ring begins to blow faintly in the wind. James notices this and tells Dustox to pull away. It does so and suddenly a sand storm tornado brews right in the middle of the field. Taillow just manages to get away but the ring is now trapped inside the vortex. The announcer wonders how this will affect the match. Ash's friends are very concerned about how the Pokemon will safely reach the ring.

James decides to wait it out but Ash has other plans. He asks Taillow if it will go into the whirlwind, and it nods. Everyone is shocked as the Pokemon flies straight in. James doesn't seem worried though. He believes Taillow will ware itself out and Dustox can just go in when it's over. Taillow is having a lot of trouble braving the winds. Ash tries to encourage it, but the tornado is just too much. Taillow falls back and Ash yells to it. The Pokemon flies back into the vortex trying to make its trainer happy. It then lets out a shrill call and begins to glow!

Ash and Pikachu watch shocked as large wings and talons grow from the Pokemon. When the glowing stops, Taillow is now a Swellow! James now becomes worried and Ash's friends have a new sense of confidence in Ash. Ash knows his Pokemon will have no trouble braving the winds now. It flies through them spinning rapidly. It doesn't seem affected by the high winds at all. Swellow smashes the vortex up and causes it to disappear.

The Pokemon then grabs the ring and races for the goal. James tells Dustox to stop it and it launches a poison sting. Swellow is hit and Dustox then tackles it. The Pokemon drops the ring and regains its senses. Both Pokemon then fly for the ring, but Ash thinks fast and tells Swellow to use wing attack. It charges up its wings and then cuts in front of Dustox smashing the ring away. The ring sails forward and gets snagged on the goal, giving Ash the victory!

Swellow flies back up triumphantly as Dustox smashes into the goal. Ash cheers and his Pokemon flies back to him. Ash scans it with the dex as James cries in his balloon. Ash's friends cheer but suddenly Team Rocket's balloon rises into the scene. Jessie begins the motto with Meowth taking James's place. When they finish the trainers notice the net full of Pokemon and demand they return them. Naturally, Jessie refuses. Ash tells Swellow to use wing attack and it flies in. The Pokemon slices the net allowing the captured Pokemon to return to their trainers.

Pikachu then thunderbolts Team Rocket's balloon and James's to send them all blasting off. James cries and Jessie and Meowth complain as they go. Ash is shown on screen with Swellow waving to the crowd as they cheer. His friends then approach and congratulate him on his victory. Max remarks that seeing Taillow evolve into Swellow was the highlight of the match. Kaito mentions that Ash and Swellow make a great team. Ash thanks him and looks at his new Pokemon. He thanks it and Swellow nods confidently. The scene then zooms in on the setting sun shining on Ash and Swellow's picture and the episode ends.

Thanks To GoldenNoctowl For Writing this for us