This chapter offers a brief overview of US relations with the Korean Peninsula from the late nineteenth century through the Trump administration to provide a historical framework for understanding the chapters that follow. While laying out this framework, this chapter also advances the argument that the policies of the Trump administration toward the Korean Peninsula were not the dramatic breaks with the past the administration often claimed they were. President Trump was hardly the first American president to be skeptical of the US alliance with the ROK and attempt to change it – though the bluntness with which he did this was unprecedented. While Trump’s three meetings with Kim Jong-un could rightly be called historic in a narrow sense, there is ample evidence they were just the latest installment of what some scholars refer to as “entrepreneurial diplomacy” with the DPRK. In the broader historical context of US relations with the Korean Peninsula, President Trump’s policies toward the ROK and the DPRK appear more as variations on a theme than dramatic breaks with the past.