Heywood is a fairly meek individual that's older than he seems. He was born after the invention of the capsule system known as Poké Balls, but his traditional upbringing from parents that did remember that time led him to respect the ways of those that lived off the land, remembering various tips and tricks about how to get along in the wilderness. As a card-carrying Liberte member, Heywood firmly believes that Pokémon and Humans should be equal in all respects under the law, and anything that gets in the way of that equality should be shunned, whether it's the League's insistence on gadgetry, Chain's preoccupation with slavery, or the Revolution deciding to segregate themselves. That being said, a Poké Ball is mighty handy.
As knowledge of the old ways is one of the few reasons for his continued freedom, he seeks out younger folk to preserve his legacy of living free and wild. Sometimes he has to do some regrettable things to maintain that independence, which draws dark-types to him like a Volcarona to a flame.