Although binding two high spin cobalt centers in close proximity proved challenging -exemplified by the synthesis of a high spin complex featuring a Co atom dangling outside of the dinucleating pocket -this was remedied by deprotonation of the PNNP backbone and the introduction of a bridging OtBu ligand. Reacting the high-spin dicobalt(II) complexes with secondary silanes yielded unusual diamagnetic dicobalt(II) complexes with two briding silicon moieties (3) and a Co-Co bond. The silicon moieties have partial silyl and partial silylene character, and are best described as base stabilized silylenes, wherein the hydrides act as a base. We hypothesize that the base-stabilized nature of the silylene moieties, diminishes the expected electrophilicity on silicon, and provides unexpectedly robust dicobalt complexes. These insights can be important for understanding potential reaction or deactivation pathways for dinuclear cobalt complexes in reactions with silanes, as well as for the design of dinuclear cobalt complexes in the future.