
Mark Kawar
Historian and business consultant, author of "America, but Bigger: Near-Annexations, from Greenland to the Galápagos" and Principal at Up One Rung.
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Oct 24, 2026
America's Failed Annexations with Mark Kawar
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Jackson van UdenHOST
But there are several parts of continental United States of America of which it doesn't make, you know, for someone just looking at the map, it doesn't make sense as to why they're not part of the United States of America, particularly when you're seeing this outward expansion kind of annexationism towards greenland the west indies and and the danish indies and the pacific there's that that slither of land that separates north western continental america from alaska and there is you know for some people as well lower california You know, were these ever considered as part of the future of America?

Mark KawarGUEST
What is now British Columbia connecting the northwest lower 48 states to Alaska was a prime annexation target, as was Baja California.

Mark KawarGUEST
The Western American-Canadian border was settled in 1846 because the two countries, British Canada and the United States, had a joint occupation agreement over this area that is now British Columbia, Washington, Oregon.
11 MINS LATER

Jackson van UdenHOST
So you know, how many kind of times you mentioned those invasions? How many times has America looked to Cuba as almost the future of America?
American Empires
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Mark KawarGUEST
If it was up to him, the U.S. would have spread over as much of the world as possible.

Mark KawarGUEST
But why Greenland specifically? After the Civil War, he was no longer concerned that expanding American territory would lead to He became more aggressive in his expansion, negotiated with Russia to purchase Alaska, and then began negotiating with Denmark to purchase the Danish West Indies.

Mark KawarGUEST
Denmark had settled these islands as a sort of commercial venture, and so it was happy to sell them for a profit.

Mark KawarGUEST
Seward wanted a US maritime presence in the Caribbean, so the two sides were negotiating and actually reached an agreement to purchase these islands.
14 MINS LATER
The Knights of the Golden Circle: America's Would-Be Slave Empire Builders?
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Mark KawarGUEST
But the Knights of the Golden Circle would come across today as ridiculous if they weren't so serious and dangerous.

Mark KawarGUEST
It was a common part of social lives for a lot of American men in the age before mass communication.
7 MINS LATER
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11:18David C. KeehnSOUNDBITE_SPEAKER
But Bickley showed up empty-handed.
William Walker: The American Adventurer Who Conquered Nicaragua
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2:56speaker_0ADVERTISER
[dramatic music]

Mark KawarGUEST
When the Spanish were in the Western Hemisphere, they wanted to spread Catholicism.

Mark KawarGUEST
That wasn't completely absent from American Manifest Destiny, but it was never the number one reason.

Mark KawarGUEST
Usually, the motivation was much more practical, whether it was a strategic port, access to fishing waters, farmland, mining, or just places to spread out.

Mark KawarGUEST
In the 19th century, Americans saw the world as ripe for the taking, and bigger was better.

Mark KawarGUEST
If there was some valuable land somewhere, someone was trying to take it, and the only things that were stopping them were geography or armed resistance.
6 MINS LATER
America's 150-Year Quest to Get Greenland
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Mark KawarGUEST
[upbeat music] In 2019, Donald Trump surprised America by talking about buying Greenland.

Mark KawarGUEST
This is something that America has done in its past, its acquired territory, but it seems strange to listeners in the 21st century.

Mark KawarGUEST
I heard the news and decided, "What would America look like if it had Greenland as well?" And then I thought, "Well, I should really add Canada and Mexico to the map because the United States has tried to acquire them in the past as well." Pretty soon, this map got bigger and bigger and more and more detailed, and I kept learning more and more stories about places around the world that could have become part of the United States, and I've learned Donald Trump wasn't the first American president who tried to acquire Greenland.

Mark KawarGUEST
The first American to get really interested in Greenland was William Seward, Abraham Lincoln's Secretary of State and probably America's most ambitious annexationist.
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5:29Wayne JensenSOUNDBITE_SPEAKER
Any impoverished monarchs retiring from the colonization business may find a good purchaser by addressing William Henry Seward, Post Office, Washington, DC."

