Herein we describe our search for a carbocation with a delocalized 5-center 4-electron C- - -H- - -C- - -H- - -C bonding array. Various helical and polycyclic molecular architectures were explored using B3LYP calculations, ultimately leading to cation 8, a remarkable species that possesses two trigonal pyramidal carbons flanking a five-coordinate trigonal bipyramidal carbon.