Gary Oak was once the most hated individual in the Pokemon franchise. Gary Oak was the main antagonist of the series for some time.
Eventually, he became a bit of an antihero. As he grew in the world of Pokemon, he proved showed himself to be more than just a punk.
Gary was always a tough challenge for Ash and most other trainers. Even after he changed his demeanor, he remained a strong battler. There were so many Pokemon he never had the chance to partner up with, though, before becoming a researcher.
Note: This article is subjective and reflects the opinion of the writer.
Top 3 Pokemon Gary should've trained in the anime
#3 - Pikachu
Seeing Gary with a Pikachu would have been incredible. No, this doesn't mean taking away Ash's Pikachu, but rather giving Gary one of his own. The Pikachu versus Pikachu dynamic would have been an amazing story in the anime.
Gary's Pikachu probably would have evolved into a Raichu eventually. That could have seen an even larger story between Ash and him, with both of them having an emotional debate on whether to evolve to keep up with Gary's Pikachu.
#2 - Lucario
It is no coincidence that a lot of Pokemon seen on Ash's team would have done incredibly well with Gary Oak as their trainer. Gary never got a chance to capture some of the newer Pokemon introduced in the franchise. Lucario would have been quite the teammate for him.
Lucario can either be a fierce and trusted partner or downright brutal in battle. Gary Oak would have taken version and run with it. Seeing Gary's intensity in battle linked with a Lucario would have been nothing short of incredible.
#1 - Charizard
Unlike the Pikachu entry, this is meant to be a trade-off. Seeing Gary Oak train the Charizard that Ash Ketchum owned would have shaken things up in the anime quite a bit. Charizard obviously didn't respect Ash at first.
It would have been very interesting to see if Charizard took more of a liking to Gary at first, seeing his power, and going down the opposite route.