Who wins in Ellen Raskin's The Westing Game?

In Ellen Raskin's The Westing Game, while it is true that Turtle Wexler figured out all four of Sam Westing's identities, won the game, and later inherited $200 million, in reality all characters in the book are winners. All characters are winners because Mr. Westing's purpose in creating the game was twofold: (1) find the best heir of the Westing fortune possible, the one who will think strategically and keep secrets--traits that are necessary for protecting the fortune; and (2) help the other characters find their own identities; in helping the characters explore and find who they are as people, he gets the opportunity to observe who they are as people.

At the beginning of the novel, the characters do not feel secure with their identities. For example, Turtle is lonely because she feels she doesn't have a real mother since she feels unloved by her mother, Grace Wexler, and Turtle's sister Angela feels she must marry Dr. Denton Deere though she doesn't want to. We learn more about the characters' unhappiness when they are asked to list their "positions" on the their receipts indicating they had received their letters inviting them to the first reading of the will. Grace shows her unhappiness when she, as the narrator describes, "wrote housewife, crossed it out, wrote decorator, crossed it out, and wrote heiress"; and Madame Hoo exhibits her unhappiness by just marking the receipt with an X to be filled out by her husband (Ch. 5).

But, by the end of the novel, all of this unhappiness has changed. Turtle feels she has found a surrogate mother in Flora Baumbach, whom she calls Baba; Angela breaks off her engagement with Dr. Deere; Madame Hoo and her husband became very financially successful due to the sales of Hoo's Little Foot-Eze; and Grace Wexler is the new happy owner of the Hoo's old restaurant, now renamed Hoo's on First, among many other happy endings. Most importantly, Turtle, the winning heiress, gained even more than just an inheritance.

Whereas once Turtle had hid her fears and anxieties behind her braid, by the very end of the story when Mr. Westing finally does truly die, she has gained a great deal of self-confidence and power. She is described by the narrator as having earned a "master's degree in business administration, an advanced degree in corporate law, [and] had served two years as legal counsel to the Westing Paper Products Corporation" (Ch. 30). We are further informed that she had "made one million dollars in the stock market, lost it all, then made five million more" (Ch. 30). In other words, she had blossomed into the type of heiress who truly could protect and even increase the Westing fortune.

Hence, while Turtle wins the game and the fortune, it can truly be said that all characters come out winners in the end--all what makes them truly happiest, what most matches their own identity.

Although there is no stated winner in the book, all the players of the Westing Game come out winners.  The idea of the book is to target relationships, and in the course of the game the players are paired with people almost exactly opposite to themselves.

However, if a winner must be announced, I would say it is Turtle Wexler.  She is the only player who discovers the true identity of the doorman, Sandy McSouthers.  He is, in fact, Sam Westing and Barney Northrup and Julian Eastman.

The book ends with Turtle visiting the aging Sandy and with information given about other players who are still in touch with one another.  Interesting friendships resulted as a result of this "experiment".

Who dies in Ellen Raskin's The Westing Game?

Sam Westing and Bertha Crow’s daughter Violet died. 

Even though she never appears in the book, Violet Westing heavily influences events.  Her death devastates her mother and father.  It is the cause of Crow’s alcoholism and mental health issues, and Sam Westing’s bizarre eccentricities.  Neither parent recovers. 

Violet Westing was supposed to be married.  She was young, and had her whole life in front of her. 

The paper king’s later years were marred by tragedy. His only daughter, Violet, drowned on the eve of her wedding, and two years later his troubled wife deserted their home. Although Mr. Westing obtained a divorce, he never remarried. (Ch. 4) 

The mystery of who killed Sam Westing stems from his daughter’s death.  Westing writes a will and concocts an elaborate game to find out which of his heirs is worthy of his fortune, but he is never actually dead.  Westing is there the whole time in his various disguises as Barney Northrup and Sandy McSouthers. 

Sam Westing has his fun, and finds that not all of his heirs are hopeless. 

His watery blue eyes stared at her over his rimless half-glasses. Hard eyes. His teeth were white, not quite even (no one would ever guess they were false). He was smiling. He wasn’t angry with her, he was smiling.

“Hi, Sandy,” Turtle said. “I won!" (Ch. 27) 

Eventually, Sam Westing does die.  He dies of old age, with Turtle by his side.  

So while there are a lot of explosions and questions about who killed Sam Westing, the only real deaths in this novel are of natural causes.  Sam Westing’s daughter drowned, and Sam Westing died of old age.  Before he died, he got to know all of his relatives a lot better.