Venous thromboembolism (VTE) is a condition in which blood clots form in the venous system of the body. It includes deep venous thrombosis (DVT) that occurs when a blood clot forms in a deep vein, more common in lower extremities, and pulmonary embolism (PE) as the clot breaks loose and travels through the bloodstream to the pulmonary arteries. VTE can result in significant morbidity and mortality. It is a preventable medical condition with the treatment being straightforward in most cases with anticoagulation and mechanical thrombectomy. Here, we discuss a rare case of a 40-year-old male with recurrent VTE that was resistant to different available therapeutic options such as direct oral anticoagulants (DOAC), vitamin k antagonists, heparin, and catheter-directed thrombolysis presenting with occlusive thrombus in the entirety of the right-sided deep venous structures, with minimal preservation of flow in the common femoral vein.