Crystals of the bis(tert‐butyl)silylene (DTBS) derivatives of the tartaric acids were synthesized from D‐, L‐, rac‐, and meso‐tartaric acid and DTBS bis(trifluoromethanesulfonate): two polymorphs of Si2tBu4(L‐Tart1,2;3,4H–4) (L‐1a and L‐1b), the mirror image of the denser modification (D‐1b) as well as the racemate (2), and the meso analogue Si2tBu4(meso‐Tart1,3;2,4H–4) (3). The structures were determined by single‐crystal X‐ray diffraction. The threo‐configured D‐ and L‐ (and rac‐) tartrates were coordinated by two tBu2Si units forming five‐membered chelate rings, whereas the erythro‐configured meso‐tartrate formed six‐membered chelate rings. The new compounds were analyzed by NMR techniques, including 29Si NMR spectroscopy, and single‐crystal X‐ray crystallography.