The combination of simultaneous rupture of a tibialis anterior tendon and Charcot neuroarthropathy of the midfoot in a diabetic patient is a rare and challenging condition that can lead to major complications if not addressed appropriately. This article discusses a tibialis anterior tendon rupture that may have developed before or after the incidence of the diabetic Charcot neuroarthropathy midfoot deformity and raises awareness to potential spontaneous tendon ruptures that may be associated with the diabetic Charcot foot.