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Scholars often rank John Tyler among the worst presidents in U.S. history. Yet his administration pursued an ambitious foreign policy: establishing a protectorate over Hawaii, opening diplomatic ties with China, pursuing naval modernization, attempting to annex Texas, settling a major border dispute with the United Kingdom, and seeking to divide Oregon Country. Tyler’s initiatives aimed to decisively establish a regional U.S. hegemony. Why did Tyler adopt such an expansive grand strategy, and why did it fail? The puzzle matters for international relations theory and foreign policy analysis, because different theories predict either that Tyler’s ambition should not have been observed or have conflicting explanations about whether it should have succeeded. I argue that Tyler’s grand strategy and its failure resulted from his lack of party affiliation combined with his single-minded drive for retaining office.