The close relation between number of π-electrons and torsion angle of the end-groups hint at a general principle. Positive charge is accommodated by twisting in both linear and spiroconjugated dications and radical cations. We will seek to outline this principle through a naive frontier MO picture; one where the change in the cation is considered on the basis that an electron is removed from the HOMO of the neutral species. We explore the two types of JT distortion by examining substituted allenes and spiropentadienes, and assess the relation between their frontier MOs and the pseudo-JT distortion in their radical cations.