Elbow dislocation may lead to disabling consequences such as elbow instability or stiffness. Complex elbow dislocation is associated with expected fracture patterns such as radial head, coronoid process, and terrible triad. On the other hand, simple dislocation is the dislocation without bony injury and is associated with a favorable prognosis. The following report describes a thirty-eight-year-old male who developed complex posterolateral elbow dislocation with irreducible trochlear fractures that blocked the reduction and mandated open reduction.