Taking its cue from Norman Rockwell’s embarrassment regarding his protruding Adam’s apple, this article focuses on the role that this embarrassment played in his development of a sense of “compromised masculinity” (Halpern 2006). This focus is informed by a discussion of the Adam’s apple from a historical and medical point of view, and by a consideration of Rockwell’s work as an artist. The article concludes with an exploration of his painting Freedom of Speech and its role in his turning of a perceived physical liability into a psychological strength and of its implications for a view of Rockwell as an agent of hope.