Water oxidation catalysis stands out as one of the most important reactions to design practical devices for artificial photosynthesis. The use of late 1st row transition metal (TM) complexes provides an excellent platform for the development of inexpensive catalysts with an exquisite control on their electronic and structural features via ligand design. However, the difficult access to their high oxidation states and the general labile character of their metal-ligand bonds pose important challenges. Herein, we explore a copper complex (12-) featuring an extended, π-delocalized, tetraamidate macrocyclic ligand (TAML) as water oxidation catalysts, and compare its activity to analogous systems with lower π-delocalization (22- and 32-). Their characterization evidences a special metal-ligand cooperativity in accommodating the required oxidative equivalents using 12- that is absent in 22- and 32-. This consists in charge delocalization promoted by easy access to different electronic states at a narrow energy range, corresponding to either metal-centered or ligand-centered oxidations, which we identify as essential factor to stabilize the accumulated oxidative charges. This translates into a significant improvement in the catalytic performance of 12- compared to 22- and 32-, and leads to one of the most active and robust molecular complexes for water oxidation at neutral pH, with a kobs of 140 s-1 at an overpotential of only 200 mV. In contrast, 22- degrades under oxidative conditions, what we associate to impossibility of efficiently stabilize several oxidative equivalents via charge delocalization, resulting in highly reactive oxidized ligand. Finally, the acyclic structure of 32- prevent its use at neutral pH due to acidic demetallation, highlighting the importance of the macrocyclic stabilization