This essay is an evaluation of how the Initial Teaching Alphabet was designed. Juliet Shen looks at the history and aesthetics of this curious “alphabet reform” which, amazingly, is still in use in the field of education. As the author herself states: “The appearance of i.t.a. on the printed page violates enough conventions of good typography to have piqued the curiosity of this writer at first sight. [. . .] How did such an anomalous typeface get designed and then selected for widespread educational use?” The story uncovered by her research contains an all-too-familiar interaction of ideology, business and politics.