Red vs Ash

[Dark Eevee]

Jea Ash would lose, but there is a way for him to win. Just remember Red only caught the first 150 Pokemon. He didn't even get Mew. And if Ash can figure out how to make Greninja more powerful, when he is Ash-Greninja, he would be able to beat Mewtwo and mega Charizard. And Red has stopped training and battling so he wouldn't become better.

 

[Legendary Jam]

I think Red would win. Not because he's Red but because his pokemon are strong. His Charizard can Mega Evolve (did anyone remember) into Charizard X which is so strong. Ash's Pikachu would get destroyed by that thing. If Ash actually used his older Pokemon like Infernape or something he could have a better chance.

Red also has some bad things. He doesn't have the best strategy for things. Red: "Oh let me use my Charmander against your Squirtle Blue" FAIL, 10/10, Best Plan- IGN

All jokes aside though.... Ash would have his butt wooped and Red would only be using his Pikachu. Because Ash doesn't use smart strategies all that much anymore. He was so much better Sinnoh.

Unova Ash: "I'm gonna fight Elesa with only My Palpitoad" 10/10, Best Plan Ever-IGN, Smartest person since Einstein

 

[MaskedKitsuneXD]

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I'd have to agree with everyone else and say that Red is definitely for the win. Red is displayed to the Pokémon community as a independent, strong, determined, and caring trainer. While Ash is also advertised this way, Ash hasn't accomplished much, or anything at all, in all of the regions he's been to. Red beat the Kanto Elite Four and even completed the PokéDex. Ash, however, was too hard-headed to do either of these things in any of the regions he's visited. Red has succeeded way more when it comes to being a true Pokémon trainer. He kept his head held high and was one with his Pokémon throughout his entire journey.

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Ash is way too focused on becoming the best of them all. Red focused on his adventure rather than this, even though being a Pokémon master was also his goal. Ash and Pikachu have a great connection, but in the manga and anime, it's obvious that Charizard and Red had a way better and stronger bond than the other two will ever have.

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I have nothing more to say about Ash or Red, though. I will say that I think both have their own good and bad qualities, but despite this, they are both good trainers with their hearts focused on the Pokémon they've bonded with.

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[Ali Younus]

Red would easily win he has very cool pokemon, he has a Mega Stone for Charizard and he has even caught a Mewtwo. Red is also the league champion, he got rid of entire Team Rocket while Ash can't get rid of Jessie and James. So Red would win easily against Ash. Mewtwo would beat all of Ash's pokemons. Also Ash has nevet won the league.

 

[Pandaxclone2]

Red would easily win he has very cool pokemon, he has a Mega Stone for Charizard and he has even caught a Mewtwo. Red is also the league champion, he got rid of entire Team Rocket while Ash can't get rid of Jessie and James. So Red would win easily against Ash. Mewtwo would beat all of Ash's pokemons. Also Ash has nevet won the league.

Ash (and by extension Pikachu) actually has no problem getting rid of Jessie, James and Meowth; the problem is that they're persistent enough to keep coming back.