The reduction of N,C,N-chelated bismuth chlorides [C6 H3 -2,6-(CHNR)2 ]BiCl2 [where R=tBu (1), 2',6'-Me2 C6 H3 (2), or 4'-Me2 NC6 H4 (3)] or N,C-chelated analogues [C6 H2 -2-(CHN-2',6'-iPr2 C6 H3 )-4,6-(tBu)2 ]BiCl2 (4) and [C6 H2 -2-(CH2 NEt2 )-4,6-(tBu)2 ]BiCl2 (5) is reported. Reduction of compounds 1-3 gave monomeric N,C,N-chelated bismuthinidenes [C6 H3 -2,6-(CHNR)2 ]Bi [where R=tBu (6), 2',6'-Me2 C6 H3 (7) or 4'-Me2 NC6 H4 (8)]. Similarly, the reduction of 4 led to the isolation of the compound [C6 H2 -2-(CHN-2',6'-iPr2 C6 H3 )-4,6-(tBu)2 ]Bi (9) as an unprecedented two-coordinated bismuthinidene that has been structurally characterized. In contrast, the dibismuthene {[C6 H2 -2-(CH2 NEt2 )-4,6-(tBu)2 ]Bi}2 (10) was obtained by the reduction of 5. Compounds 6-10 were characterized by using (1) H and (13) C NMR spectroscopy and their structures, except for 7, were determined with the help of single-crystal X-ray diffraction analysis. It is clear that the structure of the reduced products (bismuthinidene versus dibismuthene) is ligand-dependent and particularly influenced by the strength of the N→Bi intramolecular interaction(s). Therefore, a theoretical survey describing the bonding situation in the studied compounds and related bismuth(I) systems is included. Importantly, we found that the C3 NBi chelating ring in the two-coordinated bismuthinidene 9 exhibits significant aromatic character by delocalization of the bismuth lone pair.