Why do some rhodizonates neighbor one another despite such glaringly unfavorable electrostatics? And why do these anions, which are radicals, resist both Peierls and Jahn-Teller in K3C6O6, to align equidistantly instead of pairing up? Conventional face-to-face π-stacking interactions are not strong enough to overcome the electrostatic repulsion of neighboring highly charged anions. In fact, π-interactions (between closed shell ring systems) are only weakly attractive or repulsive, and typically result in T-shaped or parallel displaced configurations.