Despite numerous studies of transition metal dichalcogenides, the diversity of their chemical bonding characteristics and charge transfer is not well understood. Based on density functional theory we investigate their static and dynamic charges. The dynamic charge of the transition metal dichalcogenides with trigonal symmetry are anomalously large, while in their hexagonally symmetric counterparts, we even observe a counterintuitive sign, i.e., the transition metal takes a negative charge, opposite to its static charge. This phenomenon, so far never remarked on or analyzed, is understood by investigating the perturbative response of the system and by investigating the hybridization of the molecular orbitals near the Fermi level. Furthermore, a link is established between the sign of the Born effective charge and the process of π backbonding from organic chemistry. Experiments are proposed to verify the calculated sign of the dynamical charge in these materials. Employing a high-throughput search we also identify other materials that present counterintuitive dynamic charges.