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Holstein-Lewis fractures are spiral fractures in the distal third of the humeral shaft, which carry increased risk of radial nerve palsy compared with other humeral shaft fractures; these fractures are usually managed conservatively. However, there is no case in the existing literature that describes the management of Holstein-Lewis fractures with radial nerve entrapment in a patient with a history of total elbow arthroplasty (TEA). Here, we present the first documented case of a complex revision elbow arthroplasty for Holstein-Lewis fracture with delayed onset radial nerve entrapment after a skydiving injury. In patients with Holstein-Lewis fractures who underwent previous TEA, we identify the increased risk of nerve entrapment due to loose metallosis surrounding the fracture site and discuss the operative challenges that these rarer cases pose. We also necessitate the early monitoring of suspected neurapraxia in these patients and highlight the prognostic benefits of performing timely nerve exploration and operative intervention.