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As evidenced by the Centers for Disease Control and Prevention (CDC) statistics, syphilis is yet again on the rise. It is known as the great mimicker because of its variable symptoms and how frequently it can be confused with other diseases. The different stages of syphilis (primary, secondary, latent, late latent and tertiary) are discussed. We describe a new histopathologic pattern of syphilis, one that mimics connective tissue disease and can represent a diagnostic pitfall. In this time and age, when syphilis is rising especially among the men who have sex with men subgroup, it is important to keep a high index of suspicion of syphilis even when clinically and histopathologically the findings on first glance may not appear characteristic. [ABSTRACT FROM AUTHOR]