This chapter examines the influence that two of America's foreign policy "grandees" – former Secretary of State Henry Kissinger and former National Security Advisor Zbigniew Brzezinski – had on the Ronald Reagan and George Bush administrations' policies in the late 1980s and early 1990s. It argues that Kissinger and Brzezinski's influence illustrates the contradictory impulses in American policy at the time: one (Kissinger) emphasized the need for continuity and stability, the other (Brzezinski) highlighted the extraordinary opportunities offered by the Soviet Union's demise. Kissinger and Brzezinski's different views offer a glimpse at the uncertainty that was so evident among American policy-making elites accustomed to thinking in Cold War terms. The mix of hope and concern prevalent among American policy-making circles in the waning moments of the Cold War resulted in a policy of extreme caution and lowered expectations.