We recently demonstrated that an acyclic carbene bearing two strongly donating N-heterocyclic imine (NHI) substituents features exceptional nucleophilicity, enabling the dearomatization of a proximal inert arene ring . We reasoned that the electron-rich nature of the bis(imino)carbene, coupled with its flexible acyclic framework is an ideal platform to access a doubly oxidized carbene. Herein, we report the synthesis and isolation of a crystalline carbene dication derived from a bis(imino)carbene through a two-electron oxidation/oxide-ion abstraction strategy that bypasses the carbene radical cation (Fig. ).