In this collaborative effort with the Kozlowski and Rosenthal groups, we investigate the effect of pyridinium substituents on the efficiency of reduction and C–N bond cleavage. You may have wondered if those 2,6-aryl groups were really needed… This paper answers that question and then delves deeper into the electronic and steric factors that promote deamination. We learned so much in this collaboration and are excited to see it published in ACS Catalysis.