Before his appointment to the Supreme Court, Justice Robert H. Jackson played a highly visible role in Franklin D. Roosevelt's failed "court packing plan. " Roosevelt's legislation would have increased the size of the Supreme Court and could have dramatically altered the functioning of our government. Jackson supported the plan from his post as Assistant Attorney General. This Article uses a chronological narrative to examine Jackson's role in Roosevelt's court fight. The Article examines his role in light of the surrounding history and the tension between the backers of the New Deal and the Supreme Court. Jackson's testimony before the Senate Judiciary Committee was widely viewed as the most effective representation which the plan received. Roughly contemporaneously with his Senate testimony, Jackson gave five public addresses, some before groups adamantly opposed to the plan. Despite the poor prospects for the court legislation and his own ambivalence regarding the plan, Jackson worked loyally to sell Roosevelt's idea. This Article examines Jackson's often overlooked support of the court packing plan and provides considerable insight into the future Justice, illuminating both his strong political instincts and his blossoming abilities as an advocate.