Syphilis is coming back in the recent a few decades especially in the gay and HIV populations. Since syphilis can be "the great mimic" clinically and pathologically, a case report with updated review can be helpful to the medical community. We report, a case of syphilitic lymphadenitis diagnosed via fine needle aspiration biopsy (FNAB). The pitfalls associated with the diagnosis of syphilitic lymphadenitis will be discussed. The patient's medical records were reviewed. The pertinent history, clinical course, and ancillary studies including FNAB cytology with special stains are presented. In addition to the case report, we discuss the diagnosis of syphilitic lymphadenitis and the role of FNAB cytology. This was a 37-year-old man presenting with a two-month history of a growing neck mass, night sweats, and a ten pound weight loss. The patient had been treated one month earlier for primary syphilis. Examination of the head and neck revealed a 3 cm right level II mass. FNAB cytology showed heterogeneous population of lymphocytes and plasma cells suggesting reactive changes. Modified silver staining of the cell block slide was performed and revealed spirochetes, consistent with syphilis. The patient's lymphadenitis resolved with a course of antibiotic treatment. Although lymphadenopathy is a rare presentation of syphilis, it should be included in the differential diagnosis for patients who offer a suspect history. FNAB with silver staining is an effective, minimally invasive way to confirm the diagnosis.