America’s desire to expand its borders has existed since its first colonies – from attempts to settle beyond the Appalachian Mountains in the 18th century to Manifest Destiny in the 19th century down to talks today to purchase Greenland. But the United States spent two centuries eyeing acquisitions far stranger than California or Oregon—from Canada to the Kamchatka Peninsula of Russia and even Syria after World War I. These weren't fever dreams of fringe politicians; they were serious diplomatic efforts involving presidents, congressional debates, and appeals from foreign leaders themselves who saw American annexation as preferable to rule by Mexico, France, or Britain. The difference between success and failure often came down to whether Washington offered full statehood and constitutional protections (like Alaska and Hawaii) or imposed colonial supervision without citizenship (like Cuba and the Philippines), creating either assimilation or nationalist resentment that echoes today. Today's guest is Mark Kawar, author of America, but Bigger: Near-Annexations from Greenland to the Galápagos. We discuss how Woodrow Wilson was the last president to successfully buy land from Denmark (the U.S. Virgin Islands in 1917), why El Salvadoran leaders and Polynesian chiefs actively lobbied for American annexation to escape worse colonial masters, and how the 1919 King-Crane Commission discovered that Syria overwhelmingly requested U.S. oversight because Wilson promised self-determination while European powers reeked of imperial exploitation. Kawar also explains the Guano Islands Act of 1856, which let America claim dozens of Pacific islands for fertilizer deposits, and why American Samoans today are U.S. nationals but not automatically citizens—a legacy of the "unincorporated territory" loophole that still defines places like Guam.