Mark Twain’s “The Man that Corrupted Hadleyburg” (1899) is one of the author’s most elusive works, and many critics have attempted to make sense of the text’s confusing moral lessons. The more affirmative readings focus on the theme of the fortunate fall. This paper maintains that Twain uses the story of Mary and Edward Richards to test his readers’ ability to recognize the dark story of their utter failure that lies beneath the hopeful theme of the fortunate fall. I use the movie version (1980) as an extreme case of the popular and affirmative readings, and compare it with a critical reading that focuses on the role of Reverend Burgess and the inner trials of the Richards.Burgess has been read as an innocent victim of the town’s hatred and as its communal conscience. In the town-hall meeting he protects Edward in order to repay him for what he mistakenly thinks is a past debt for Edward’s kind help. His un-reading of Edward’s letter, however, functions as a new temptation to the Richards, and his unintended bait is far stronger and easier to take, because Edward misunderstands that Burgess had lost his letter, and that nobody knows his dishonesty.Twain makes the readers feel pity and sympathy for the poor old couple. The story seduces the readers to feel that Edward is quite honest when he makes a public confession from his deathbed. The real purpose of his public confession is, however, to blame Burgess: Edward wrongfully claims that Burgess changed his mind when Edward’s servant betrayed his secret wrong done to Burgess in the past, and that Burgess exposed his guilty letter to the people in revenge. Edward’s generous gesture of forgiving Burgess is another wrong done to Burgess.The critical look at the role of Burgess and the nature of the inner struggle of the Richards cautions the readers not to take for granted the optimistic interpretation of the story.