A 42-year-old Italian homosexual presented with a red painful eye associated with exudative retinal detachment that was subsequently attributed to syphilitic posterior scleritis. These findings all resolved with intravenous penicillin therapy. However, choroidal mass lesion persisted and subsequent ancillary imaging including B scan and ultrasonography confirmed the presence of a choroidal melanoma, which was treated with radioactive plaque therapy. This case report will describe the interesting findings of this unique presentation.