Our work outlines several connections between the π-system topology and the structure of linear and spiroconjugated molecules. First, we have demonstrated a simple mnemonic that assumes extensive electron delocalization by considering the Möbius or Hückel topology of the system. Furthermore, assessment of the LOL isosurfaces indicate that there is helical electron delocalization in the radical cations. Most significantly, our results reveal that the helical frontier π-MOs are the driving force for the JT distortion in allene and spiropentadiene cations. We show this can be considered as a helical π-conjugation effect, which provides more stabilization than the equivalent linear π-conjugation.