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As U.S.-PRC security and economic rivalries intensify, the Donald Trump administration is increasingly elevating U.S.-Taiwan relations and becoming more vocal about supporting the island democracy in order to confront Beijing’s assertiveness. Washington’s explicit promotion of a series of pro-Taiwan initiatives and overtures, including the president’s signing of the Taiwan Travel Act (March 2018) and Asia Reassurance Initiative Act (December 2018), has led to speculation that America is retreating from its decades-old One-China policy. While President Trump’s National Security Strategy has viewed China as a “strategic competitor” seeking Indo-Pacific hegemony and displacing the United States in global preeminence, Washington’s cozying up with Taipei is compatible with realist strategic logic. Using content analysis, this research purports to examine how the Trump administration explains and describes America’s One-China policy, comparing and contrasting from those of the Barack Obama administration. We utilize the text data, such as presidential speeches, statements, White House press releases and the State Department briefings, and provide numeric scores evaluating both administrations’ positions on One-China policy. The analysis reveals that the Trump administration has indeed made some notable, though cautious, adjustments on the U.S. One-China position. This research then provides rich implications to the existing Washington-Beijing-Taipei relations.