Ellen Raskin's working title for The Westing Game was "Eight Imperfect Pairs of Heirs," so this is a fun question to explore! Although the sixteen heirs seem to be unlikely partners at first, we know that every part of the game is intentional, and the characters learn that there are benefits in whom they were partnered with.
Chris Theodorakis is wheelchair bound and has trouble speaking due to a medical condition. People often overlook him because he has trouble expressing himself, but we see that he is thoughtful, considerate, smart, and observant.
Dr. Denton Deere initially passes judgment in being paired with Chris. He feels that he is not a caretaker to freely give medical advice. However, he softens up as he gets to know Chris. Their partnership is highly beneficial, as Dr. Deere learns to be kinder and eventually helps Chris get the revolutionary medical treatment he needs.
As two high-school boys, Theo Theodorakis and Doug Hoo are excited to be paired together and "slap hands." Indeed, this pairing seems to make the most sense upfront. Aside from Theo's desire to be with his brother, he is friends with Doug and they already have a way of relating to each other. Theo displays great initiative in playing the game. Doug seems to not be of much help at first, but we do see ways that they work together. For example, when Theo suspects Otis, Doug's speed allows him to follow Otis to discover the truth.
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