Pseudoaneurysm of the ascending aorta is a rare complication of cardiac surgery occurring in less than 0.5% of cases. Deep sternal wound infections (DSWI) increase the likelihood of aortic pseudoaneurysm. An ascending aortic pseudoaneurysm has high morbidity and the mortality rate has ranged from 29%-46% in the medical literature. We report a complex patient who underwent an AVR at an outside hospital complicated by DSWI requiring pectoral flap coverage. Months later, he was transferred to our institution with acute swelling of his sternum, diagnosed as massive aortic pseudoaneurysm originating from the cannulation site.