Enantioenriched 1,4‐dicarbonyl compounds are versatile synthons in natural product and pharmaceutical drug synthesis. We herein report a mild pathway for the efficient enantioselective synthesis of these compounds directly from aldehydes through synergistic cooperation between a neutral eosin Y hydrogen atom transfer photocatalyst and a chiral rhodium Lewis acid catalyst. This method is distinguished by its operational simplicity, abundant feedstocks, atom economy, and ability to generate products in high yields (up to 99 %) and high enantioselectivity (up to 99 % ee). It takes two: Enantioselective synthesis of 1,4‐dicarbonyl compounds directly from readily available aldehydes was accomplished with good yield and enantioselectivity through the synergistic combination of a neutral eosin Y hydrogen atom transfer photocatalyst and a bis‐cyclometalated rhodium catalyst.