While pnictaalkenes are well‐established for the light group 15 elements, they become more reactive and exceptionally rare as the group is descended. Herein, we report a combined experimental and theoretical study on the first examples of carbodicarbene (CDC)‐stabilized bismuth complexes, which feature low‐coordinate cationic bismuth centers with C=Bi multiple bond character. Monocations [(CDC)Bi(Ph)Cl][SbF₆] (8) and  [(CDC)BiBr₂(THF)₂][SbF₆] (11), dications [(CDC)Bi(Ph)][SbF₆]₂ (9) and [(CDC)BiBr(THF)₃][NTf₂]₂ (12), and trication [(CDC)₂Bi][NTf₂]₃ (13) have been synthesized via sequential halide abstractions from (CDC)Bi(Ph)Cl₂ (7) and (CDC)BiBr₃ (10). Notably, the dications and trication exhibit C⇉Bi double dative bonds, and thus represent unprecedented bismaalkene cations. In addition, the synthesis of these species highlights a unique non‐reductive route to C–Bi π‐bonding character. The CDC‐[Bi] complexes (7‐13) were compared with related NHC‐[Bi] complexes (1, 3‐6) and show substantially different structural properties. Indeed, the CDC ligand has a remarkable influence on the overall stability of the resulting low‐coordinate Bi complexes, suggesting that CDC is a superior ligand to NHC in heavy pnictogen chemistry. All compounds have been characterized by multiple analytical methods including ¹H and ¹³C NMR, X‐ray crystallography, elemental analysis, and UV‐Vis spectroscopy. In addition, the bonding situation was analyzed with modern charge and energy decomposition analysis.