May-Thurner Syndrome is a vascular condition in which chronic compression of the left common iliac vein by the overlying right common iliac artery causes impaired venous return from the left lower extremity as well as possible development of pelvic varicosities. The condition typically presents with acute left lower extremity deep vein thrombosis or with signs and symptoms of pelvic or lower extremity venous insufficiency. In our patient, however, the presenting symptom was hemorrhage of pelvic varicosities in the setting of extensive pelvic fractures sustained during a motor vehicle collision. Acute hemorrhage in the setting of pelvic fractures is typically associated with the need for arterial angiography and possible embolization. This patient was instead treated with venography and stenting of her May-Thurner lesion which resulted in the resolution of her bleeding pelvic varicosities and improvement in her pre-existing pelvic and lower extremity venous symptoms.