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Venothromboembolic (VTE) events are considered rare complications following foot and ankle surgery. Most instances of VTE following surgical procedures occur in particularly high-risk patient populations; therefore, VTE prophylactic anticoagulation is initiated based on risk/benefit stratification for each individual patient undergoing foot and ankle surgery. We present a case report on a 40-year-old male who underwent isolated Lisfranc ligament repair and subsequently developed an acute saddle pulmonary embolism and deep vein thrombosis 1 month postoperatively. The patient was on prophylactic Lovenox, yet still developed a life-threatening complication. The patient was found to be on a selective estrogen receptor modulator for the off-label treatment of male infertility. This medication, surgical intervention, and a period of non-weight bearing are believed to be contributory to the patient's relatively increased hypercoagulable state. This case depicts a rare complication of foot and ankle surgery and highlights the importance of VTE prophylaxis during the postoperative period.