More than thirty years after the discovery of a stable carbene, this work shows that a doubly oxidized carbene can be isolated as well. In his Nobel lecture, Olah stated, "it should be clear that in carbocationic systems, varying degrees of delocalization always exist ." Despite the cumulenic delocalization of the positive charges, carbene dication 1 2+ displays significant electrophilicity at the dicoordinate carbon center. It is amenable to two successive nucleophilic attacks, in line with the existence of two accessible coordination sites at the central carbon. We also show that it can participate in an unprecedented reversible two-electron redox system with parent bis(imino)carbene, fully consistent with its description as a doubly oxidized bis(imino)carbene. This work demonstrates that bulky strong electron-donor substituents can be used to mask both vacant orbitals at the central carbon atom and prevent the two anions from coordination, paving the way for the isolation of a variety of doubly oxidized carbenes.