Syphilitic hepatitis is a rare manifestation of syphilis with an incidence of 0.2-38%. We describe a case of a healthy, immunocompetent male patient with elevated liver function tests (LFTs) who was found to have syphilitic hepatitis. A 28-year-old male with no past medical history presented with abdominal pain for two to three weeks. He also reported diminished appetite, intermittent chills, weight loss, and fatigue. His history was positive for high-risk sexual behavior including multiple partners and absence of using protection. His physical examination was remarkable for right-sided abdominal tenderness and a painless chancre on his penile shaft. His workup revealed elevated aspartate aminotransferase (AST: 169 U/L), alanine transaminase (ALT: 271 U/L), and alkaline phosphatase (ALP: 377 U/L). His abdominal CT scan was unremarkable except for the abdominal and pelvic lymphadenopathy. A thorough serology panel revealed negative hepatitis A, B, C, human immunodeficiency virus (HIV) (including HIV RNA), Epstein-Barr virus (EBV), and cytomegalovirus (CMV). His immunological workup was negative as well. His rapid plasma reagin (RPR) was reactive with positive IgG/IgM treponemal antibodies. He was managed as secondary syphilis and received 2.4 million units of benzathine penicillin. Upon follow-up after one week, he reported a complete resolution of his symptoms, and his LFTs were normalized on a repeat checkup. Given the significant morbidity associated with a missed diagnosis, syphilitic hepatitis should be considered an essential part of the workup for evaluating elevated LFTs in an appropriate clinical setting. This case also highlights the importance of obtaining a comprehensive sexual history and performing a thorough genital examination.