Density functional and correlated ab initio methods were used to calculate, compare, and analyze bonding interactions in late-transition-metal alkyl and heteroatom complexes (M-X). The complexes studied include: (DMPE)Pt(CH3)(X) (DMPE = 1,2-bis(dimethylphosphino)ethane), Cp*Ru(PMe3)(2)(X) (Cp* = pentamethylcyclopentadienyl), (DMPE)(2)Ru(H) (X), (Tp)(CO)Ru(Py)(X) (Tp = trispyrazolylborate), (PMe3)(2)Rh(C2H4)(X), and cis-(acac)(2)Ir(Py)(X) (acac = acetylacetonate). Seventeen X ligands were analyzed that include alkyl (CR3), amido (NR2), alkoxo (OR), and fluoride. Energy decomposition analysis of these M-X bonds revealed that orbital charge transfer stabilization provides a straightforward model for trends in bonding along the alkyl to heteroatom ligand series (X = CH3, NH2, OH, F). Pauli repulsion (exchange repulsion), which includes contributions from closed-shell d(pi)-p(pi) repulsion, generally decreases along the alkyl to heteroatom ligand series but depends on the exact M-X complexes. It was also revealed that stabilizing electrostatic interactions generally decrease along this ligand series. Correlation between M-X and H-X bond dissociation energies is good with R-2 values between 0.7 and 0.9. This correlation exists because for both M-X and H-X bonds the orbital stabilization energies are a function of the orbital electronegativity of the X group. The greater than 1 slope when correlating M-X and H-X bond dissociation energies was traced back to differences in Pauli repulsion and electrostatic stabilization.