During periods of national and global crises, both British Prime Minister Winston Churchill and American President Barack Obama have demonstrated a clear mastery of leveraging strategic communication to inspire people. Given the benefit of hindsight, we realize that Churchill went a step further, successfully using his ability to connect with people to facilitate the accomplishment of his grand strategy. We cannot yet ascertain to what degree President Obama will be successful on this account. However, we can already see similarities between the manner and the purposes for which Churchill and Obama used their unique verbal abilities.Churchill used strategic communication to rally his domestic constituency, to articulate values and to build strong partnerships as a means to win World War II. Obama is clearly following Churchill’s lead in each of these areas. As a relative neophyte on the national stage, he garnered a wave of domestic support for “change we can believe in” and rode it to a sweeping electoral win. His decisions to close Guantánamo Bay and to end policies that some view as torture are ways in which Obama has emphasized national values, similar to Churchill’s focus on freedom and perseverance. Obama’s diplomatic overtures also already resemble those of Churchill. Like Churchill’s persistent yet patient wooing of the Americans to join the Allied cause during World War II, Obama has employed a humble yet concerted effort to renew strong ties with Russia, to realize a world without nuclear weapons and to court Europe through his initial presidential visits and through his choice of Prague as the site for a key policy speech.This paper focuses on Churchill’s use of strategic communication to accomplish his grand strategy of winning the war and creating a new world order based on peace and freedom. In the process he influenced the fate of his nation and the world. Despite critics who would dismiss Obama’s strategic communication as “all talk” and call for substance to follow speech, Churchill’s leadership of Britain during World War II serves as an important reminder of the impact of a gifted orator in shaping destiny.