In 1982, during the Reagan revolution, the United States Postal Service issued a commemorative stamp to honor Horatio Alger, Jr., author of 100 books for boys, 1864-1899. Vignettes on the official postcard portray scenes of fisticuffs and striving; Alger appears stern, with the steadfast visage of a captain of industry. Nothing reflects Alger’s mild demeanor or his true heroes, who were kind and always reached their modest successes through wise mentors who recognized the boys’ character. How did the legacy of the “real” Alger, a Progressive-era reformer who worked to reduce inequality, morph into the harsh “bootstraps” mythology now associated with his name? How did he become a symbol for free-market competition despite his community-oriented messages? Answers lie in businessmen’s reactions against the New Deal. Individualist popularizers with business support, such as Norman Vincent Peale, distorted Alger into a model to legitimate inequality. They solicited businessmen’s support to establish organizations and scholarships in Alger’s name. Alger’s latter-day devotees insisted that upward mobility evinced merit and condemned all who had not moved upward as unworthy of respect or aid. They succeeded in making Horatio Alger and his once popular stories a paradoxical source of legitimacy for inequality.