The medial ligaments of the ankle are injured more often than generally believed. Complete deltoid ligament tears are occasionally seen in association with lateral malleolar fractures or bimalleolar fractures. Chronic deltoid ligament insufficiency can be seen in several conditions, including posterior tibial tendon disorder, trauma- and sports-related deltoid disruptions, and valgus talar tilting in patients who have a history of triple arthrodesis or total ankle arthroplasty. This article focuses on the anatomy and function of the medial ligaments of the ankle and establishes a rationale for the diagnosis and treatment of incompetent deltoid ligament.