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This study reports the invention of di‐ or trifunctionalization of readily available pyridines (including all the pyridine substrates utilized in this paper, such as 3‐cyanopyridine and 3‐chloropyridine) through dearomative functionalization‐oxidative rearomatization under transition‐metal‐ and reductant‐free conditions. Although a two‐step operation is required, the crude product of the first step could be used in the next step directly. Typically, 3‐π‐EWG pyridines undergo difunctionalization, whereas 3‐σ‐EWG pyridines participate in trifunctionalization, affording multisubstituted piperidines. Computational studies provide detailed insights for their distinct reactivity in the title reaction. [ABSTRACT FROM AUTHOR]