This article presents the case of a 52-year-old man with a chronic anterior shoulder dislocation accompanied by a massive Hill-Sachs lesion. The dislocation occurred 6 weeks prior to presentation as the result of a seizure. At the time of the initial injury, the patient was treated in the emergency department and told that his shoulder was reduced. Despite this, he continued to experience pain and inability to move his shoulder. Repeat radiographs and magnetic resonance imaging (MRI) revealed an anterior shoulder dislocation with a massive Hill-Sachs lesion that was locked onto the anterior glenoid. Attempts at a gentle closed reduction in the operating room failed, necessitating an open reduction that involved an extensive capsular release and a Bankart repair. The Hill-Sachs lesion was managed with a humeral head-plasty performed with an 8-mm anterior cruciate ligament guide (Smith and Nephew, Andover, Massachusetts) placed adjacent to the lesser tuberosity. The Hill-Sachs lesion was tamped out to restore the contour of the humeral head and back filled with allograft. Postoperative MRI of the shoulder revealed successful restoration of the contour of the humeral head, although avascular necrosis was present. At 6-month follow-up, the patient reported no instability or pain and had resumed his activities of daily living without difficulty. He regained forward flexion of 165 degrees, abduction of 160 degrees, internal rotation of 75 degrees, and external rotation of 70 degrees. This article presents the successful management of a large, engaging Hill-Sachs lesion using a novel bone-tamping technique that provides an alternative to coracoid transfer procedures and osteochondral allografting.