An aldimine bearing a 3‐methyl‐2‐pyridyl group undergoes [2+2+2] cycloaddition reaction with two alkyne molecules under nickel catalysis to afford a 1,2‐dihydropyridine derivative in moderate to good yield. The reaction is likely to involve oxidative cyclization of the imine and alkyne, insertion of another alkyne, and CN reductive elimination, followed by a 1,5‐sigmatropic hydrogen shift. The pyridyl group is proposed to facilitate the reaction by chelation to the aza‐nickelacycle intermediates.