Syphilitic aortitis is a rare complication of tertiary syphilis, which can lead to aortic aneurysm formation, aortic valvular insufficiency, and ostial coronary stenosis. Syphilis has re-emerged worldwide over recent decades and vascular surgeons should be aware of its cardiovascular manifestations. Atypical clinical presentation, such as hemoptysis and a computed tomography angiography pattern of a thicker aneurysmal wall with ulcer-like aneurysm projections, should raise suspicion of syphilitic aortic aneurysm. An early diagnosis and appropriate surgical and medical therapies significantly contribute to successful treatment and favorable prognosis. Herein is reported the case of an 82-year-old male patient, positive for syphilis infection, with impending aortic arch aneurysm rupture treated with a hybrid arch repair. After 7 months, the patient was brought to the emergency room in cardiac arrest. Unsuccessful cardiopulmonary resuscitation maneuvers were performed, and an autopsy showed cardiac tamponade due to rupture of the ascending aorta.