Since the beginnings of professionalization in the nineteenth century, architects have struggled to find ways to reach a broad public. Leopold Eidlitz, one of the founding members of the American Institute of Architects, published a series of essays in The Crayon in 1858 that attempted, through the use of popular literary forms, to do just that. Eidlitz addressed the “Discourses Between Two T-Squares” to a general audience and hoped that their humor and scathing caricatures would educate non-professionals about the practical and theoretical intricacies of architecture. Eidlitz’s attempt at advocacy sheds light on the long-standing difficulty that architects have faced in their attempts to create a resonant public image.