Ligand-based functionality is a prominent method of increasing the reactivity or stability of metal centers in coordination chemistry. Some of the most successful catalysts use ligand-based redox activity, pendant protons, or hemilability in order to specifically accelerate catalysis. Here we report the diimino-pyrrole ligand (DIPyH)-D-Tol,Cy ((DIPy)-D-Tol,Cy = 2,5-bis(N-cyclohexyl-1-(P-tolyl)methanimine)pyrrolide), which exhibits all three of these ligand properties. Metalation of (DIPy)-D-Tol,Cy to Pd gives the pseudo-square planar complex ((DIPy)-D-Tol,Cy)PdCl, which upon reduction forms a mixture of products, including a Pd(I)-Pd(I) dimer wherein (DIPy)-D-Tol,Cy bridges the dimeric unit. Upon addition of PMe3, the imine arms of ((DIPy)-D-Tol,Cy)PdCl are displaced to yield ((DIPy)-D-Tol,Cy)Pd(PMe3)(2)Cl, where the (DIPy)-D-Tol,Cy ligand binds in a monodentate fashion. This complex can be reduced to generate a ligand-based radical, as shown by EPR spectroscopy. Finally, ((DIPy)-D-Tol,Cy)PdCl also can be protonated at the imine arm, exhibiting a total of three different coordination modes across this series of complexes. Taken together, these studies show that (DIPy)-D-Tol,Cy exhibits notable flexibility in its coordination and redox chemistry.