The proliferation of psychoanalytic schools demands the reexamination of the history of psychoanalysis. Psychoanalysis emerged at the intersection between the rational heritage of the enlightenment and the interest in the morbid that was the hallmark of romanticism. This paper focuses on moments when psychoanalysis was poised at a crossroads where various routes could have been taken. Differentiation is made among the heretics, modifiers, and extenders of psychoanalysis. Discussed within a historical frame of reference are the contributions of leading modifiers—Melanie Klein, Hartmann, Winnicott, Kohut, and others—as well as their extenders. The paper concludes with a discussion of some current urgent problems facing psychoanalysis.