What happened to Biff from "Death of a Salesman" in high school that suggested he would not likely succeed in his life as an adult?

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The two traits that Biff acquired during his youth, but especially during his high school years, that kept him from success as an adult were dishonesty and an inflated sense of his own abilities. Toward the very end of the play, just a few pages before the Requiem, Biff faces the truth about himself and shares his revelations with Willy.

First, he says that the entire family "never told the truth" to each other. Evidence of that includes Willy's affair that he never confessed to Linda; Biff's unwillingness to tell Willy or anyone why he "gave up" on college; Hap's exaggeration about his job title; and Willy's lies about money and his job. Beyond that, Willy raised the boys to steal. They stole the lumber for their front stoop from a nearby construction site, and Biff admits that he "stole [himself] out of every good job since high school." Even while he was in school, apparently, he stole sporting balls. Eventually, Biff ended up in jail for three months for stealing a suit, and he...

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