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May-Thurner syndrome is a rare condition requiring both clinical acumen and correct imaging studies to diagnose. We present a case of a 49-year-old male who was initially admitted for chest pain and was later found to have extensive left-lower-extremity deep vein thrombosis. Subsequent computed tomography (CT) imaging was able to reveal a right common iliac aneurysm compressing the left common iliac vein. Radiologic findings and procedural angiographic studies are reviewed with reference to pertinent literature.