Stable helical radicals are promising multi‐functional molecules in light of intriguing magnetic and chiroptical properties. Attempts were made to extend diphenylmethyl‐fused NiII porphyrin radical to helical system as the first air‐stable organic neutral helical radicals. Intramolecular Pd‐catalyzed twofold C−H arylation of methyl‐ or methoxy‐introduced meso‐diphenylmethyl NiII porphyrins gave a mixture of the target and rearranged radicals. Oxidative fusion reaction of meso‐(bis(1‐naphthyl)methyl) NiII porphyrins provided doubly fused NiII porphyrin radicals. One of the helical radicals was separated into enantiomers that showed mirror‐image circular dichroism (CD) spectra up to 1300 nm. The helical dinaphthylmethyl‐fused NiII porphyrin radical displayed solid‐state magnetic property mostly arising from monomeric radicals, different from the parent diphenylmethyl‐fused NiII porphyrin radical that showed antiferromagnetic coupling due to π‐stacked pairing. Radical behavior: Diarylmethyl‐fused NiII porphyrin radicals have been extended to a helical system as the first air‐stable organic neutral helical radicals. Di(1‐naphthyl)methyl‐fused NiII porphyrin radicals thus synthesized were separated into enantiomers that showed mirror‐image CD spectra up to 1300 nm, indicating the effective desymmetrization of the frontier molecular orbitals.