May-Thurner Syndrome (MTS) is a rare anatomical variant characterized by the compression of the left common iliac artery by the right common iliac artery against the fifth lumbar vertebrae. It can present as acute or chronic deep vein thrombosis (DVT), leg pain, varicosities, skin ulceration, and hyperpigmentation. In this case report, we present an interesting case of a young male with no obvious risk factors, who presented with back and left lower extremity pain later diagnosed with MTS on computed tomography angiography (CTA) and venogram. The patient was treated with venoplasty and pharmacomechanical thrombolysis and was discharged on apixaban.