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Most scholars and pundits today view Franklin Delano Roosevelt and John F. Kennedy as aggressive liberal leaders, while viewing Schlesinger's famous histories of their presidencies as celebrations of their steadfast progressive leadership. A more careful reading of Schlesinger's work demonstrates that he preferred an ironic political outlook emphasizing the virtues of restraint, patience, and discipline. For Schlesinger, Roosevelt and Kennedy were liberal heroes and models as much because they respected the constraints on their power and ideals as because they tested traditional institutions and redefined the boundaries of presidential power.

Aggressive liberalism involves the use of inspirational rhetoric and cunning political tactics to expand civil liberties and insure economic equality. Schlesinger's emphasis on the crucial role that irony has played and should play in liberalism poses a challenge to the aggressive liberalism advocated by liberal activists, political thinkers, and pundits. That his counsel was grounded in conservative insights as well as liberal values makes it accessible to leaders across the political spectrum.