This essay examines the Army’s efforts to cultivate and gain congressional support for the GI Bill in the 1980s. Focusing on the relationship between Representative Sonny Montgomery, senior Army leaders like Maxwell R. Thurman and Robert Elton, and the staffers who worked for each of them, it illustrates the intentionality with which Army leaders worked to cultivate congressional support for and to head off congressional and presidential opposition to a bill that they saw as essential. Analyzing their public and private efforts at critical moments when the legislation was imperiled reveals that relations between the Army and Congress are more intricate than testimony at hearings and budget requests might reveal, that throughout the 1980s, Army leaders remained deeply concerned about sustaining the All-Volunteer Force, and that the ultimate success of that force and the legislation that helped ensure it rested with individuals who built and then leveraged personal relationships.