During the past 5 years we encountered 16 cases of necrotizing funisitis, a deeply seated inflammatory process within the matrix of the umbilical cord, and established that all of them were associated with maternal and congenital syphilis. During that time necrotizing funisitis was not found to be associated with any other infection. The relationship was unexpected on the basis of current knowledge of the condition, but we found the older medical literature documents syphilis as the virtually specific cause of deep funisitis with angiophlebitis. Necrotizing funisitis has a characteristic macroscopic appearance, the "barberpole" cord, that permits the presumptive diagnosis of congenital syphilis at the time of birth.