

Red and Ash are both pretty similar characters in concept, but their character personalities do tend to differ. Ash is a pretty happy trainer, but his Pokemon knowledge tends to evaporate over time. (Unova) His strategies aren’t the best, but his Pokemon do the best that they can. Red is pretty intense and he became the Pokemon Master. That’s something that Ash has always wanted to do, but he never could. Still, thanks to all of the various anime, Ash has enough pokemon to win this battle. Ash wins.
Update. Thanks to the Pokemon Origins special (Which I recommend), Red now has enough pokemon to completely destroy Ash. He has Mewtwo, Jolteon, Pikachu, and dozens of others at his disposal. I don’t really think that Ash has a chance anymore. Not even Pikachu can defeat an entire army! Red wins.
Ash Ketchum was based on Red…
Anyway, Red is more competent and actually has aged properly. How Ash is still 10 after so many years is a wall banger.
Also, I doubt these two guys would battle except for a training exercise. They’d probably be friendly.
Yeah and I always have a hard time choosing which character I like better. Red has that silent but powerful feel to him while Ash just seems more determined and ready to win. His eternal life serum is definitely working quite well.
That said, in the end I agree they would hit it off pretty well