Syphilis has long been known as the great imitator. Its heterogeneity can manifest in the form of meningitis, space occupying gummas, vasculitis, strokes, cranial neuropathies, myelopathy, dementia, and seizures. The incidence has been rising with each year, mainly in men who have sex with men accounting for 83% of cases. With the coexistence of immunocompromised states, especially HIV (human immunodeficiency virus), the usually chronic and insidious course of tertiary neurosyphilis can be accelerated. Stroke can occur as a result of neurosyphilis in its meningovascular form, and the likelihood of this increases with HIV co-infection, especially in high-risk groups such as intravenous drug users and men who have sex with men. Here, we discuss a case of a young man who presented with an ischemic stroke found to have neurosyphilis and HIV and consider the management of these co-morbid conditions.