Elbow dislocations are a high-energy traumatic event resulting in loss of congruence of a stable joint. The majority of elbow dislocations can be reduced by closed means and treated conservatively. We present a case of an irreducible elbow dislocation with reduction blocked by the radial head buttonholed through the lateral ligamentous complex. We performed open reduction with release followed by repair of the lateral ligamentous complex. Clinicians need to understand this unique variant of an elbow dislocation to appropriately treat this operative injury.