Foot ulcerations complicated by infection are the major cause of limb loss in people with diabetes. This is especially true in those patients with severe sepsis. Determining whether to amputate or attempt to salvage a limb often requires in depth evaluation of each individual patient's physical, mental, and socioeconomic status. The current report presents and juxtaposes two similar patients, admitted to the same service at the same time with severe diabetic foot infections complicated by sepsis. We describe in detail the similarities and differences in the clinical presentation, extent of infection, etiology, and socioeconomic concerns that ultimately led to divergent clinical decisions regarding the choices of attempting diabetic limb salvage versus primary amputation and prompt rehabilitation.