The antiaromaticity of a series of dianions of p-substituted benzylidene dibenzo[a,d]cycloheptenes was examined through calculated measures of antiaromaticity. The nucleus-independent chemical shifts (NICS) and magnetic susceptibility exaltation both showed substantial antiaromatic character in the benzannulated tropylium anion. When the antiaromaticity was normalized for the area of the ring, these tropylium anions were shown to be among the most antiaromatic anions in the chemical literature. Attempts to make the dianion through reduction with lithium or potassium gave the tetraanion as the only species observable in the 1H NMR spectrum. Quench of the reaction mixture with trimethylsilyl chloride or D2O confirmed the presence of the tetraanion, but only as a small portion of the reaction mixture, with the major product being unreacted starting material. The failure to observe starting material was attributed to similarities in the structures of the starting material and anion radical (first reduction), allowing rapid electron transfer between them. The inability to see the dianion (second reduction) could be the result of the very small HOMO–LUMO gap anticipated for highly antiaromatic species, which would allow access to diradical species. The magnitude of the HOMO–LUMO gap was determined by the difference between the HOMO and LUMO energies from geometry optimization and the lowest energy transition from TD-DFT calculations. The HOMO–LUMO gap for the benzylidene dibenzocycloheptatriene dianions was shown to be much smaller than the HOMO–LUMO gap of species for which 1H NMR spectra had been observed.