Peri-trochanteric fractures with an extension into the femoral neck are relatively rare. Due to the lack of a defined treatment in the literature, these fractures pose a challenge to orthopedic surgeons. This case report highlights the value of timing to surgical intervention, choosing the appropriate operative course, not treating very important person (VIP) patients differently than standard patients, and decreasing unnecessary costs for the patient and the US healthcare system.An 85-year-old male VIP patient presented to the emergency department (ED) with a left peri-trochanteric fracture with an extension into the ipsilateral femoral neck. The initial plan was to perform arthroplasty with diaphyseal fixation. However, the community-based hospital would have to wait two to three days for the proper implants, and the patient insisted on being treated at this hospital. Due to concerns about increased mortality with delayed treatment, the patient underwent short cephalomedullary nail (CMN) fixation the next day. On postoperative day (POD) 49, a pop was heard and felt while ambulating, and radiographs revealed substantial lateral cutout of the CMN and subsidence of the femoral head. On POD 54, the patient underwent a successful left total hip arthroplasty using a modular diaphyseal press-fit femoral component, which resulted in an uneventful recovery. This case illustrates a cautionary tale in choosing the appropriate operative course for a VIP patient with a peri-trochanteric fracture extending into the femoral neck (a relatively rare fracture type that has no clearly defined treatment option). This is imperative to reduce pain and length of stay for the patient, postoperative complications, and cost. Based on the results from the second procedure and weighing the risk of prolonged treatment, the authors believe that this patient would likely have benefited from a primary arthroplasty procedure given his body habitus and complex fracture pattern.