Although the majority of F. Scott Fitzgerald's stories were published in popular magazines with illustrations, little scholarly attention has been paid to the hundreds of images that interpreted Fitzgerald's stories or to the artists who produced them. Yet, for most of Fitzgerald's contemporary audiences, these illustrations played an essential role in how they experienced the text, particularly given the usual placement of an image preceding, and thereby framing, the narrative. One of Fitzgerald's most important stories, “The Rich Boy,” was published in two installments of Red Book Magazine in January and February of 1926, and was illustrated by F. R. Gruger, a prolific and well-respected illustrator at the peak of his career. Examining the interplay between Gruger's six illustrations and Fitzgerald's text reveals how they mutually reinforce Fitzgerald's narrative and thematic emphases through prefiguring, highlighting, and interpreting elements of the plot. By focusing on this aspect of the print culture surrounding the publication of Fitzgerald's stories, this article demonstrates the integral link between the visual and textual during this era and offers new ways of thinking about how Fitzgerald's stories were positioned for most of his contemporary readership.