Gary

Gary Oak is the grandson of Professor Samual Oak and former long time rival of Ash since they were kids.

Bio
Gary started his Pokemon journey with a Squirtle and got way ahead of Ash winning gym bages and catching more than 75 pokemon in the Kanto and Johto regions. He sometimes makes fun of Ash and teases him until he was defeated by him at the Silver Conference with Charizard defeating his Blastoise. After that, he decided to follow in the footsteps of his grandfather becoming a Pokkemon researcher.

Although Gary hasnt met May before she went to Johto, he did meet Dawn in Sinnoh while protecting the Shieldon from the sinister Hunter J.