Metal-ligand cooperativity is ubiquitous throughout both biological and chemical catalysis, but often goes unattributed or underutilized in organic catalysis. Practically, utilizing every resource available and not discriminating metal vs. ligand is a powerful strategy to getting more tunability as well as more efficiency in any kind of chemical transformation, and nature, and an ever-increasing number of chemists, realizes this. By building in this biomimetic strategy, first row metals can also be enhanced past their native one-electron preferences, opening the door to multi-proton, multi-electron chemistry. In particular, hydrogen transfer chemistry is important due to its wide variety of applications in industrial processes and pharmaceutical development. For this reason, there has been extensive research into catalyst design for reactions involving hydrogen transfer reactivity. Homogenous catalysts are attractive for studies due to the relative ease of their characterization. However, any reaction that involves the movement of protons and electrons, even in a redox-neutral fashion, can benefit from a multifunctional ligand. In these studies, a 2,5-dihydrazonopyrrole (tBu,TolDHP) ligand scaffold, which has previously been shown to store a full H2 equivalent (in addition to any redox-capabilities of the metal center), was utilized in complexes with Co, and with these complexes alone, I show the diversity of reactivity, enhanced and altered selectivity, and broad applicability afforded by ligands as complex as the metals they bind. Not only have I demonstrated the capability of these ligands to stabilize unusual motifs, such as a rare oxidation state of TEMPOH2+ and a potassium-capped cobalt-oxido, but I have done reductive, oxidative, and redox-neutral catalysis, utilizing heat, electrochemical potential, and light to drive reactivity different directions. Specifically, I have been able to accomplish reductive hydrogenation of olefins to alkanes, with distinctive terminal selectivity and a mechanism that features ligand-based H-atom equivalents and key radical intermediates. On the oxidative side, I have been able to showcase the unusual selective formation of hydrogen peroxide from water, which can be rendered catalytic with oxidative potential (chemical or electrochemical). Lastly, I have investigated redox-neutral olefin isomerization, with the ability to use heat or light to switch between thermodynamically preferred or contra-thermodynamic products respectively. This work highlights how a proton- and electron-storing ligand can access and access broad and varied reactivity with a first-row metal and is not limited to any one class of reaction.