What makes somebody a Loser, a person doomed to unfulfilled dreams and humiliation? Nobody is born to lose, and yet failure embodies our worst fears. The Loser is our national bogeyman, and his history over the past two hundred years reveals the dark side of success, how economic striving reshaped the self and soul of America.

From colonial days to the Columbine tragedy, Scott Sandage explores how failure evolved from a business loss into a personality deficit, from a career setback to a gauge of our self-worth. From hundreds of private diaries, family letters, business records, and...