Chronic lateral ankle instability may be present in as many as 10% to 30% of people suffering from acute lateral ankle ligament injuries. Ankle instability has been referred to as either functional instability or mechanical instability. Management options consist of either nonoperative or operative treatment, with the majority of the literature emphasizing operative management for chronic instability. Long-term studies assessing the different types of available operative repairs have now been published. This review article discusses chronic lateral ankle ligament instability from a functional, anatomical point of view. The indications for treatment, nonoperative and operative treatment, as well as the biomechanical information available regarding these methods of treatment are considered. The major emphasis of this review is discussion and analysis of the many different surgical treatment options. Following this review, we presently recommend anatomical repair to the bone of both the anterior talofibular ligament and the calcaneofibular ligament, together with imbrication of the ligaments. In patients with hypermobility, long-standing instability, or arthritis, reconstruction using the Chrisman-Snook technique is recommended.