Ionic bonds are attributed to differences in the intrinsic electronegativity of interacting heteroatoms. In contrast, homoatomic interactions are often associated with varying degrees of electron sharing, resulting in a spectrum of bond types ranging from weak metallic to strong multiple covalent bonds. Among the elements, carbon is particularly notable for its ability to form robust covalent bonds with other carbon atoms, giving rise to a vast array of hydrocarbons and extended networks in its allotropes. However, reports of carbon-based ionic salts remain scarce. A few ionic carbon-carbon bonds have been reported in substituted stable aromatic ions and fullerenes with bulky substituents in polar solvents. In these systems, positive and negative charges are typically delocalized over the conjugated molecular cores and shielded by bulky protecting groups. These groups effectively isolate the carbanion's electron pair from the lowenergy orbital of the carbocation, maintaining stability. Here, we present a novel strategy to stabilize a carbanion and a carbocation in close proximity, separated by only the length of a σcovalent bond.