The development of durable platinum-group-metal-free oxygen reduction reaction (ORR) catalysts is a key research direction for enabling the wide use of fuel cells. Here, we use a combination of experimental measurements and density functional theory calculations to study the activity and durability of seven iron-based metallophthalocyanine (MPc) ORR catalysts that differ only in the identity of the substituent groups on the MPcs. While the MPcs show similar ORR activity, their durabilities as measured by the current decay half-life differ greatly. We find that the energy difference between the hydrogenated intermediate structure and the final demetalated structure (ΔEdemetalation) of the MPcs is linearly related to the degradation reaction barrier energy. Comparison to the degradation data for the previously studied metallocorrole systems suggested that ΔEdemetalation also serves as a descriptor for the corrole systems and that the high availability of protons at the active site due to the COOH group of the o-corrole decreases the durability.