Stewart serves as Chairman of Crossroads Strategies, LLC. Stewart served as Legislative Director to Senator Richard Shelby (R-AL) from 1992-1996. During his tenure, Stewart acquired a substantial background in defense policy, appropriations, financial services, and Senate procedure. In 1999, He and his longtime business partner Johnson M. Green, founded Federalist Group, LLC.
Under his guidance as CEO, Federalist Group was ultimately acquired by Ogilvy Public Relations in 2005, having become one of the largest advocacy firms in Washington, D.C., despite having one of the smaller lobbying teams comparable to other similarly positioned firms in the space. Stewart and his partners have always emphasized the quality and cohesion of their team over quantity of personnel. This philosophy continues today at Crossroads Strategies where the firm enjoys a deep roster of high-quality clients served by an impactful team of the highest competence and work ethic.
While at Federalist Group, and later as Managing Director of Ogilvy Government Relations, Stewart was instrumental in altering and amending federal policy in the areas of telecommunications, defense, transportation, and financial services.
Known for his strategic acumen, ability to manage multifaceted advocacy campaigns and build teams uniquely designed for individual client campaigns, Stewart is widely acknowledged as one of the Washington consulting community’s leading lobbyists to emerge from Capitol Hill in the past two decades.
Active in campaigns and elections, Stewart also lends his time and strategic advice to numerous candidates for state and federal office. A Summa Cum Laude graduate of the University of Alabama, Stewart earned his MA and Ph.D. in Government from the University of Virginia.