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Mark Kawar

Mark Kawar

Historian and business consultant, author of "America, but Bigger: Near-Annexations, from Greenland to the Galápagos" and Principal at Up One Rung.

Oct 24, 2026

13:14
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?
14:04
19th century Americans were looking at the map just the same way that you were.
14:08
And you're absolutely right.
14:10
What is now British Columbia connecting the northwest lower 48 states to Alaska was a prime annexation target, as was Baja California.
14:22
So let me talk about both of those stories in turn.
14:26
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.
14:44
They called it the Oregon Country.

11 MINS LATER

26:03
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?
18:52
Why did Seward want Greenland?
18:55
So first of all, Seward wanted almost anywhere.
18:58
If it was up to him, the U.S. would have spread over as much of the world as possible.
19:02
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.
19:23
So these are the islands that are now the US Virgin Islands.
19:26
Denmark had settled these islands as a sort of commercial venture, and so it was happy to sell them for a profit.
19:33
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

34:05
When did that happen?
4:01
How much of this could be true?
4:04
I'm Mark Khawar.
4:05
I'm the author of America, But Bigger.
4:07
It's a real thing.
4:08
But the Knights of the Golden Circle would come across today as ridiculous if they weren't so serious and dangerous.
4:17
[upbeat music] Secret societies were very popular in the mid-19th century.
4:23
It was a common part of social lives for a lot of American men in the age before mass communication.

7 MINS LATER

David C. KeehnSOUNDBITE_SPEAKER
11:18
But Bickley showed up empty-handed.
speaker_0ADVERTISER
2:56
[dramatic music]
2:57
When the Spanish were in the Western Hemisphere, they wanted to spread Catholicism.
3:02
They wanted to spread Spanish civilization.
3:06
That wasn't completely absent from American Manifest Destiny, but it was never the number one reason.
3:14
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.
3:25
In the 19th century, Americans saw the world as ripe for the taking, and bigger was better.
3:32
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

10:04
[metal clinking]
2:39
Let's get into the story.
2:40
[upbeat music] In 2019, Donald Trump surprised America by talking about buying Greenland.
2:49
This is something that America has done in its past, its acquired territory, but it seems strange to listeners in the 21st century.
2:58
[record scratches] And I made a map.
3:00
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.
3:28
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.
3:38
Here's Wayne Jensen of the Alaska Historical Commission with more on this man.
Wayne JensenSOUNDBITE_SPEAKER
5:29
Any impoverished monarchs retiring from the colonization business may find a good purchaser by addressing William Henry Seward, Post Office, Washington, DC."

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