Entrapment of the long head of the biceps tendon in proximal humeral fractures is an uncommon pathology described in the literature in rare cases especially in the pediatric population. Clinical presentation may be misleading, and the diagnosis of proximal humeral shoulder fractures with or without biceps tendon entrapment could be missed on plain radiographs and even on 3D reconstruction CT scan. Interposition of the long head of the biceps in complex proximal humeral fractures may be a challenge for proper anatomical percutaneous or open reduction of these fractures. The following case report describes a case of a patient involved in a ski accident falling on an outstretched arm with an atypical presentation of long head of the biceps (LHB) tendon entrapment in a multi-fragmentary depressed intra-articular proximal humeral fracture. The patient underwent prompt surgical intervention.