User:StarSword
I've played at least one game from every generation of the Pokemon series. (The bold-face type indicates the trainer name.)
Generation I Trainers
In Blue Version my character David M began with a Squirtle named Squirty, eventually becoming a Blastoise.
In Pokémon Yellow Version my character McVeren began with a Pikachu named Shocky.
Generation II Trainers
In Gold Version my character Aaron (my real name, incidentally) started with a Cyndaquil named Firequill that eventually became an extremely powerful Typhlosion.
Generation III Trainers
In Sapphire Version my character Sylvia started with a Torchic named Blazer that eventually bacame a Blaziken.
In Fire Red my character Hitomi started with a Charmander named Firestorm that eventually became a Charizard.
Generation IV Trainers
In Pearl Version my character Chip started with a Chimchar named Firebolt that eventually became an Infernape.