The stepwise 1-3 electron reduction of the N-alkyl substituted bis(imino)pyridine cobalt dichloride complexes, ((R)APDI)CoCl2, was studied where (R)APDI = 2,6-(RN=CMe)(2)C5H3N, R = C6H11 (Cy), CHMe2 (Pr-1). One electron reduction with either zinc metal or NeBEt3H furnished the bis(imino)pyridine cobalt monochloride compounds, ((R)APDI)CoCl. X-ray diffraction on the ((iPr)APDI)CoCl derivative established a distortion from square planar geometry where the chloride ligand is lifted out of the idealized cobalt-chelate plane. Superconducting Quantum Interference Device (SQUID) magnetometry on both compounds established spin crossover behavior with an S = 1 state being predominant at room temperature. Computational studies, in combination with experimental results, establish that the triplet spin isomer arises from a high spin Co(II) center (S-Co = 3/2) antiferromagnetically coupled to a bis(imino)pyridine chelate radical anion, [PDI](-) (S-pDI = 1/2). At lower temperatures, the Co(II) ion undergoes a spin transition to the low spin form (S-Co = 1/2) and antiferromagnetic coupling gives rise to the observed diamagnetic ground state. Replacing the chloride ligand with a methyl group, namely ((R)APDI)CoCH3, also yielded distorted compounds, albeit less pronounced, that are diamagnetic at room temperature. Two electron reduction of the ((R)APDI)CoCl2 derivatives with excess 0.5% sodium amalgam or 2 equiv of NaBEt3H furnished the bis(chelate)cobalt complexes, ((R)APDI)(2)Co, while three electron reduction with 3 equiv of sodium naphthalenide yielded the cobalt dinitrogen anions, [Na(solv)(3)][((R)APDI)CoN2] (solv = THF, Et2O). Both bis(chelate) compounds were crystallographically characterized and determined to have S = 3/2 ground states by SQUID magnetometry and electron paramagnetic resonance (EPR) spectroscopy. Computational studies, in combination with metrical parameters determined from X-ray diffraction, establish a high spin (S-Co = 3/2) cobalt(II) center with two bis(imino)pyridine chelate radical anions. Antiferromagnetic coupling between the two chelate centered radicals is mediated by a doubly occupied t(2g) cobalt orbital and gives rise to the observed overall quartet ground state.