Hewitt served as a special assistant to Attorney General Edwin Meese III in the Reagan administration's Department of Justice, providing advisory support on legal and policy matters during a key period of conservative judicial appointments.

Mark Levin served as Chief of Staff to Ed Meese at the Department of Justice, where Meese personally mentored him and guided his career in conservative legal advocacy. Meese remains a close professional ally and currently serves alongside Levin on the Board of Directors of the Landmark Legal Foundation.

Edwin Meese III, a founding member of the Federalist Society and a veteran of the Reagan administration, served as a mentor and senior advisor to Leonard Leo since the early years of Leo's career and involvement with the organization. Meese's experience, his influence in conservative legal circles, and his role in shaping Reagan-era judicial appointments and conservative legal policy provided a model and guidance for Leo's own work, including specific guidance on judicial selection strategies, strategic initiatives within the Federalist Society, and introductions to influential conservative networks. Their relationship has encompassed private meetings, collaborative projects, and Meese's public endorsements of Leo's work. Meese's institutional influence helped shape Leo's conservative legal philosophy, strategic approach to judicial nominations and advocacy, and his efforts in expanding the Federalist Society's influence and advancing its judicial agenda, which is evident in Leo's later work with the organization and his role in advising Republican administrations on judicial appointments. Leo has frequently cited Meese as a key figure in shaping his views on the role of the judiciary and the importance of conservative legal activism. Meese also provided guidance to the Federalist Society itself, helping to shape its role in promoting originalist and textualist judges during the Reagan administration and beyond.

Leonard Leo has maintained a private communication channel with Edwin Meese III to coordinate conservative judicial strategy and nominations. This channel has been used to discuss potential Supreme Court nominees, legal theories, and long-term strategies for shaping the federal judiciary. Their communications have included undisclosed meetings and phone calls that were not part of official Federalist Society or government channels, often involving other key conservative legal figures such as Robert P. George and Steven G. Calabresi.