In cardiological practice, there may be patients with chest pain and heart failure of a specific etiology, including an association with cardiovascular syphilis. This article describes a 49-year patient with chest pain, heart failure, and neurological symptoms associated with ongoing tertiary syphilis. The history included an antisyphilitic treatment 30 years before the current hospitalization. Further evaluation confirmed neuro- and cardiovascular syphilis with severe aortic regurgitation and syphilitic myocarditis. Tertiary syphilis is a rare but relevant challenge for various medical specialists, including cardiologists. This pathology requires increased medical alertness and interdisciplinary interaction for early diagnosis, effective and safe treatment, and improved prognosis.