Colonel Pickering isn't a character so much as a narrative device. His presense appears to challenge Higgins' ideas, but he's actually just a sounding board, an opportunity for Higgins to say what he's thinking out loud. If Pygmalion had been a novel, Shaw could have indulged in a lot of interior monologues and Pickering might well have never existed.
Also, since Pickering and Higgins both came from at least the upper middle-class, Pickering's ideas about the gaps between the haves and the have nots are kind of academic, and not much different from the doubts Higgins certainly had about his own theories.
Pickering was similar to Dr. Watson (Sherlock Holmes' sidekick) in this regard. Pickering doesn't really drive any of the action and things happen despite him, not because of him. Really, he could be a figment of Higgins' imagination, like Tyler Durden (from Fight Club). A "bet" is the hoariest of all possible plot devices (a dance competition is a close second) and it's the weakest element of Pygmalion.
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