Spontaneous coronary artery dissection (SCAD) is a rare diagnosis that presents both a diagnostic and therapeutic challenge. This disorder is rare but more often found in young and pregnant females. The diagnosis of SCAD is difficult as the presenting signs and symptoms may be non-specific. The treatment for SCAD may often be conservative if the patient does not have acute coronary syndrome. Patients who experience dissection are at risk for future events. We present a case of a 44-year-old male with a history of smoking and hypertension who presented with chest pain and syncope. He was found on angiogram to have an SCAD.