We describe the formation of a stable triplet-state oligoaniline di(cation radical) via a proton-triggered odor reaction between N,N’-bis[4-(phenylamino)phenyl]-1,3-benzenediamine (1) and N,N’-bis[4-(phenylimino)cyclohexa-2,5-dienylidene]-1,3-benzenediamine (2). In this reaction 1 is oxidized, while protonated 2 is reduced, both yielding the same di(cation radical) 1(2 . 2+). The di(cation radical) is characterized with UV/visisble/near-IR and ESR spectroscopy (D = 118 MHz; E approximate to 0 MHz). Variable-temperature ESR measurements are consistent with a triplet ground state fur 1(2 . 2+), The high stability of 1(2 . 2+) under ambient conditions demonstrates that alternating meta and para oligoanilines are interesting building blocks for future polaronic ferromagnets.