This article analyzes the letters exchanged as part of the clinical weight management of President William H. Taft, one of the first public figures in U.S. history to be defined popularly in terms of his pathologic obesity. In 1905, Taft hired Dr. Nathaniel E. Yorke-Davies, an English diet expert, to supervise a weight-loss plan. Taft corresponded extensively with Yorke-Davies over the next 10 years, receiving and responding to courses of treatment via post. This correspondence is one of the few archival collections documenting physician and patient perspectives on the treatment of obesity, and it took place at the precise moment when obesity began to be framed as both a serious and medically manageable condition. This intimate clinical history of the 27th president and 10th chief justice of the Supreme Court offers a unique opportunity to examine in detail the history of the obesity experience in the United States, and it sheds light on the almost-timeless challenges of creating and maintaining long-term treatment courses for conditions like obesity.