Subclavian artery occlusion (SAO) is a rare form of peripheral artery disease, sometimes associated with arterial thoracic outlet syndrome (ATOS). Subclavian arterial and venous occlusions are often misdiagnosed initially, and their clinical presentation can be confusing in bodybuilding athletes with increased vascularity in combination with anabolic steroid use. We present a 63-year-old male weightlifter with a history of hypertensive cardiomyopathy, renal transplant with left upper extremity arteriovenous fistula and subsequent takedown, cervical spinal stenosis, left rotator cuff surgery, and decades of testosterone injections who presented with years of left shoulder and neck pain. After having seen multiple providers and being diagnosed with various common disorders, CT angiography and conventional angiography were eventually performed and confirmed the presence of chronic SAO. The chronic occlusion was not deemed amenable to surgery or endovascular intervention and was treated medically with anticoagulation. Although anabolic steroid use is associated with arterial thrombosis, to our knowledge, this is the first reported case of SAO in a weightlifter. Initial misdiagnosis resulted in a long and costly workup. Although the patient’s symptoms were consistent with occlusion (and his increased vascularity could potentially suggest chronic thrombosis of any kind), these key signs were masked given his weightlifting history, anabolic steroid use, and concurrent degenerative musculoskeletal conditions common to the weightlifting population. A thorough history, comprehensive physical examination, appropriate imaging studies, and a high index of suspicion for vascular occlusion in athletes who use steroids are critical for the timely diagnosis and treatment of SAO.