We describe a case of a 36-year-old man who presented with stroke in the right paramedian pons in the pontine perforator territory, manifesting as intermittent headache, slurred speech, left-sided weakness, and paresthesia. This case highlights the diagnostic challenge in identifying neurosyphilis as a cause of stroke in young individuals. Clinicians should maintain vigilance for this uncommon etiology through conducting a detailed history and investigation in susceptible patients with key risk factors. Once the diagnosis was confirmed in our case, a multidisciplinary approach was used for management with neurologists, infectious disease specialists, and the neurointerventional team. Our patient ultimately underwent successful therapy with mechanical thrombectomy for basilar artery thrombosis from meningovascular syphilis.