Although the Korean Peninsula has been divided for over 70 years, North and South have not been able to make lasting progress in terms of reconciliation. While there are multiple factors directly influencing the extent to which inter-Korean relations can progress, this paper focuses on the role of the United States. When it comes to inter-Korean reconciliation efforts, is the U.S. more of a facilitator or a spoiler? By looking at three case studies spanning three South Korean administrations—Roh Tae-woo, Roh Moo-hyun and Moon Jae-in—this paper attempts to find patterns and lessons related to Washington’s role in the complex inter-Korean reconciliation process. The cases reveal that the U.S. has played the role of both facilitator and spoiler in each case, and that whatever role the U.S. plays depends on its own relationship with North Korea at that time. The U.S. is most likely to play a facilitating role when the administrations in Washington and Seoul are both willing to engage diplomatically with Pyongyang, when progress is being made in denuclearization talks, when the geopolitical environment is conducive towards diplomacy and engagement with North Korea, and when the U.S. adopts a reciprocal negotiating strategy. The paper concludes by considering the conditions necessary to achieve inter-Korean reconciliation and to establish long-term peace on the peninsula. Key factors include the need for trust-building and reciprocity between the U.S. and North Korea, and adopting a more holistic approach that goes beyond the nuclear problem and aims to establish a lasting relationship between Washington and Pyongyang.