Unveiling May-Thurner Syndrome in a Case of Recurrent Deep Venous Thrombosis With Bilateral Pulmonary Embolism

May-Thurner syndrome (MTS) is a rare cause of deep venous thrombosis (DVT), characterized by the external compression of the left common iliac vein by the right common iliac artery against bony structures. Risk factors for MTS include female sex (postpartum, multiparous, and using oral contraceptive pills), spinal abnormalities like scoliosis, prior aortoiliac vascular stent placement, dehydration, and hypercoagulability. MTS patients with partial obstruction can be asymptomatic, but progression to extensive symptomatic DVT and/or chronic venous insufficiency can occur. MTS can be diagnosed by non-invasive imaging studies including ultrasound (US), computed tomography (CT) scan, magnetic resonance imaging (MRI), venogram, catheter-based venogram, and intravascular US. For MTS patients with moderate to severe symptoms, we suggest thrombectomy, angioplasty, and stenting of the affected segment. In this case report, we highlight a 44-year-old male with a recent diagnosis of left-sided DVT on apixaban who presented with worsening leg swelling. DVT, pulmonary embolism (PE), and MTS were diagnosed with a lower extremity US, chest CT angiography, and abdominal/pelvic CT scan and venography, respectively. The patient underwent interventional radiology-guided local thrombolysis, thrombectomy, and venoplasty along with stent placement in the left common iliac vein. Subsequently, the patient was discharged on rivaroxaban.