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Syphilis has long been referred to as the “great mimicker” because of ts often protean clinical manifestations and the fact that the delay between primary infection and onset of clinical symptoms can be weeks to years. In addition, the clinician’s ability to elicit a history of potential exposure may be hindered by the stigma of its sexually transmitted nature and associated reticence of disclosure. The causative organism (Treponema pallidum) has the ability to directly affect a wide variety of anatomic sites including the skin, eyes, joints, kidneys, gastrointestinal tract, central nervous system, and cardiovascular system. Liver involvement (syphilitic hepatitis), in particular, carries a significant risk of oversight as both laboratory findings and histological changes in the liver are highly variable and relatively nonspecific. Thus, familiarization with the clinical and histopathologic diversity of syphilitic hepatitis by both pathologists and clinicians is crucial for timely diagnosis and treatment.