I choose Giovanni because with Pokemon Trainer, they represent the four main 'classes'. Evil teams, players/rivals, champions and gym leaders.
Meowth was a given for Giovanni's Pokemon.
I choose Marowak because it is a ground type, and Giovanni does use it. The evolutionary line is part of the story mode of the Kanto games, and they are associated with Team Rocket.
I choose Nidoqueen because she is one of Giovanni's most icconic Pokemon. She has appeared in the manga. She is also used in the most battles out of all of Giovanni's Pokemon.
A lot fo Pokemon could be used, but these three go with Giovanni's character more.
Also, should I make a thread where I have an achieve of the icons I made?
Also, if I needed to cut the roster down to fifty, the following characetrs would be cut
Toad
Dixie Kong or K Rool
Anna
Chibbi Robo
Giovanni
Tetra
Lip, Takamaru or Duck Hunt Dog
Dillon or Wonder Red
Isaac or Shulk
and Waddle Dee