In this article, the author draws on his experience as Loewald's analysand to explore Loewald's outlook on therapeutic action. Selected references from Loewald's writings and commentary about him from others amplify this exploration. The author also notes how his analysis informed his own development as an analyst, and comments on analytic training in the late 1960s. In addition, he describes Loewald's unique position as a linchpin between ego psychology and the contemporary analytic schools of thought that are based on a two-person psychology.