In the Bay of Pigs, Vietnam, and the 2003 Iraq invasion, strategic calculation, systematic probing of assumptions combined with multiple advocacy and creative thinking, and skilled implementation may have led to decisions not to commit U.S. power and prestige in the first place, or have led to better outcomes. There is no shortage of need to apply these lessons with discernment as the U.S. faces contemporary challenges including the Iranians’ suspected nuclear weapons program, North Korea’s nuclear program and periodic provocations, the Arab Spring, a rising China, terrorism and transnational crime, climate change, and potential pandemics. It is possible, by chance, to have a good outcome in these and other challenging situations without a good decision-making process, but those chances are not high. It is incumbent upon the president to lead his national security team wisely to stack the odds as best as possible in the U.S.’ favor.