The working title for The Westing Game was "Eight Imperfect Pairs of Heirs." The Westing game arranges the sixteen heirs into pairs, each provided with $10,000 and a set of word clues. For example, Chris Theodorakis, a young birdwatcher with a crippling disease, is paired with Denton Deere, a young doctor and the fiance of Angela Wexler. Angela, a beautiful but unwilling bride-to-be, is paired with Sydelle Pulaski, an eccentric secretary and publicity seeker. Judge J. J. Ford is paired with the doorman, Sandy, who begs her to stay in the game—even though she disapproves of it—because his wife and family need the money.
Everyone gains from the relationship with his or her partner. Turtle perhaps gains the most since her partner, the dressmaker Flora Baumbach, gives her the love Turtle's mother has always withheld. Flora gains a surrogate daughter to ease the pain caused by the death of her own little girl. As they seek the Westing fortune, each pair becomes a partnership and eventually part of the community.
One of the major questions in the novel is why Sam Westing—a man known for his patriotism, his love of theatrical disguises, and his sharp business practices— chose these heirs and designed the game. Although he speaks through a will, Sam Westing is a central character in the novel, and his personality and motivations are important to the plot.
Every character in The Westing Game has a significant role, but the three most important characters are Turtle Wexler, Angela Wexler, and Judge J. J. Ford. Turtle and Angela, sisters who both have their share of intelligence and determination, seem to be opposites in many ways. Angela, the blonde and beautiful eldest daughter of Gracie and Jake Wexler, is being forced into an early marriage with the young doctor, Denton Deere. She would like to go to college, but her mother, who has always doted on Angela, has swept aside her objections and launched her on a round of showers, trousseau gifts, and gowns. Angela wanders blankly through this scene, clutching a large bag of embroidered household linen. Angela's experience in The Westing Game shows her. that a young woman cannot allow other people to take away her identity and the right to her own decisions. Angela's route to selfhood, although a weirdly original one, is satisfactory and successful.
While Angela has been idolized and praised for her beauty, Turtle is neglected and unloved. She has brains and pluck, however, and is quick to find the love she needs. The Westing Game gives Turtle a chance to play the stock market (she reads the slogan at the end of the will, "Buy Westing Paper Products," as an investment tip), adopt Flora Baumbach as her grandmother, and manipulate the Westing heirs into compassionate treatment of an accused murderer. Raskin's summary at the end of her first novel, The Mysterious Disappearance of Leon (I Mean Noel), says "some achieve fame, others love." In this novel Turtle manages to secure both.
Josie-Jo Ford, a judge for the appellate division of the state supreme court, is the most unusual candidate for Westing's heir. She is the only character who actually knew Sam Westing and she believes that he is manipulating the heirs into a game that will hurt someone— probably his wife, who left him after their daughter's suicide. Judge Ford is not trying to win the game to gain the fortune but to outsmart the master at his own game.
The lawyer stammered an apology to the still-standing woman. "I was only reading; I mean, those are Mr. Westing's words." Judge Ford's...
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belief that Sam Westing was a wicked man may have some basis in fact. Westing's success undoubtedly involved connivance and a ruthless temperament. But a lack of self-confidence plays a major role in her suspicions. Judge Ford was the daughter of a servant in Westing's house. She received her fine education from Westing, who coached her in chess when she was a little girl and then ensured that she was given a proper chance. Although she knows she has fine qualifications for her position as a judge, in her less confident moments she fears that she was given the job because Westing wanted influence in the courts. One of the happiest outcomes ofThe Westing Game is that it frees Judge Ford of her bitterness and turns her instead into a satisfied benefactor.