A case of vertical transmission in a 35-year-old pregnant woman, gravida 4, para 2 with an unknown medical history of carrying primary syphilis is described. A routine 3rd trimester scan was performed at 30 + 5 weeks of pregnancy, which revealed fetal growth restriction (FGR) associated with absent fetal movement, a pathologic neuroscan characterized by cortical calcifications and ominous Doppler waveform analysis of the umbilical artery and ductus venosus. Computerized electronic fetal monitoring (EFM) showed a Class III tracing, according to the American College of Obstetricians and Gynecologists (ACOG) guidelines. An emergency C-section was performed and a female newborn weighing 1470 g was delivered. The Apgar scores were 5 and 8 at the first and fifth min, respectively. Besides the prompted obstetrical and neonatal interventions, the neonate died after 7 days. A histologic examination of the placenta revealed a chorioamnionitis at stage 1/2 and grade 2/3. The parenchyma showed diffuse delayed villous maturation, focal infarcts, and intraparenchymal hemorrhages. The decidua presented with chronic deciduitis with plasma cells. The parents declined the autopsy. Congenital syphilis is an emerging worldwide phenomenon and the multidisciplinary management of the mother and the fetus should be mandatory.