Captain Cook and Kermit Roosevelt: Alaska’s Untold Stories

Scott and Jenn dive into a whirlwind of adventure as they chat about Jenn’s trip to Alaska, where she got to explore some seriously cool historical spots.

First up, she visited the Captain James Cook Statue in Anchorage, learning about the man who helped map Alaska and how the city got its name—spoiler alert, it has his name written all over it!

Then, she took a moment to pay her respects at the grave of Kermit Roosevelt, Teddy Roosevelt’s son, which has its own intriguing backstory. With tales of glaciers, moose sightings, and the stunning Alaskan wilderness, Jenn paints a vivid picture of her travels while Scott throws in his usual witty banter.

So grab a cozy drink and join us for a history-filled chat that’s as entertaining as it is enlightening!

Links referenced in this episode:


📍 Google Maps to Alaska History spots

🎥 Video version of this podcast

💬 Comment on this episode below

Transcript

152 alaska draft good audio

Jenn: [00:00:00] An explorer from England and he sets out to map the land areas of the world, 

How does Anchorage get its name? 

if you add all the land area of all the West Coast bases together, it doesn’t even equal the land area of the base in Anchorage, Alaska. 

Scott: That’s how far north you are going and that’s why it’s light at 3:00 AM. 

Jenn: And the British had their rifles and guns with him and to sh as a show of force, 

Scott: there was people from Australia saying, yeah, here in Australia, captain James Cook is a big deal. He’s considered our Christopher Columbus for, for Australia.

Jenn: And what’s interesting during World War II is this area is very close to Japan. 

So I just made me really feel like if you want that kind of adventure, that last frontier, that, explorer mentality.

Alaska is that place. 

When you think of the Roosevelts, that is quintessential American Dynasty right there, ​

[00:01:00]

Introduction to Talk With History

Scott: Welcome to Talk With History. I’m your host Scott here with my wife and historian Jen. 

Jenn: Hello. 

Scott: On this podcast, we give you insights to our history inspired world travels YouTube channel journey, and examine history through deeper conversations with the curious, the explorers, and the history lovers out there.

Jen’s Alaska Trip with Pinups for Vets

Scott: We are talking about your recent trip back in April, a couple months ago. To Alaska and so. For folks who may not be familiar with the charity work that you’ve been doing it’s nonprofit organization called Pinups for Vets that gave you the opportunity to go out to Alaska and you took advantage of that to do some kind of history side trips.

Tell us a little bit about that. 

Jenn: So. Pinups Fortes is a nonprofit where they make a calendar and every girl in the calendar is a veteran, and I was a part of the 2025 calendar. I missed October. I’m the only Navy veteran in that calendar, and it’s great because October is the Navy’s birth month and [00:02:00] it’s the Navy’s 250th birthday this year, which I’m super proud to represent and be a part of.

What happens is after this calendar is made, we will visit veteran homes and veteran hospitals and we sign the calendar for free to patients and veterans there. And I’ve done the veteran home in Kentucky. I’ve done the veteran home in Mississippi and. I signed a hundred calendars, I spent hours there, and some of those veterans never get visitors and their faces just light up when you walk in.

I dress 1940s pinup, and I sign the calendar for them and I talk to them. I ask ’em about their service and where they’re from, and it’s just really great because I give them something that they can put up in their room. But it’s also great to talk about their service and thank ’em for their service and, and give them a visit when.

A lot of ’em don’t get visitors. So the mission of pinup cts [00:03:00] was to visit all 50 states, and Alaska was the last state. We hadn’t been to Alaska. So our. Our founder, Gina, had set up this trip for seven Pinups to go to Alaska, visit the VA homes there. The base the VFW it was just a, a lot of different.

Locations there. Plus they have some non veteran nonprofits there that take veterans out on excursions. And one of them was a glacier trip, so we got to do a glacier trip. So it was a great opportunity for me since I had never been to Alaska. I was asked to go. I was super, I was super honored to be selected, and so, yeah, I got to go to Alaska. I had never been to Alaska, so we flew into Anchorage and spent. About five days in Anchorage. And like I said, we were like nonstop visiting all these places. Just pin up the whole time, signed calendars, met people, was fantastic.

And while I [00:04:00] was there I thought I’ll try to do some history. And I was able to do two things because our days were booked, but I was able to get the van. One early morning and before the rest of the girls woke up, I was able to get out and do two things. I visited the Captain Cook statue in downtown Anchorage, and I did the grave site of Kermit Roosevelt, which is on Fort Richardson Cemetery National Cemetery, which is on the base there in Anchorage.

So. I was able to do those two things before the girls actually even woke up. So if you see the videos, it’s early morning because it’s like summer, coming to summertime in Alaska, the sun rises very early. 

Scott: The snow’s still melting. 

Jenn: Yes. And, but it’s bright. So like even at 3:00 AM 4:00 AM the, it was bright so I could get out there.

Even though it’s freezing, I could film because you had lights. So I was able to do those two things and do some history there in Anchorage. 

Giving Back

Scott: Yeah, and so to set the stage a little bit further, 

Scott: [00:05:00] one of the cool things that, as we’ve been doing, walk With History, the YouTube channel, and talk with history, this podcast as we’ve been doing that.

We’ve been I, I don’t know if building a business out of it is, is really the, the best way to describe it. But, looking for opportunities and, and, and Pinups for Vets was one of these opportunities. It was like something that we’ve been doing this channel and you’ve got an opportunity to.

To work with a nonprofit and going out there doing something that, that we do care about. Mm-hmm. Talking to veterans and visiting veterans. And so that’s just been really cool to this channel, the support that our audience, that you guys listening, that you guys watching give us, gave us that opportunity to, to do this for a nonprofit.

And it’s really cool. And Gina. She’s been very supportive of, of you and getting you on the local radio station and now you’re on it monthly and, and all this stuff. And so we love to be able to, to give back and this was just a really cool opportunity. But you did sneak away for a little bit and [00:06:00] you got to go visit a site where they had a statue to Captain James Cook.

And then later and we’ll, we’ll talk about both of these a little bit more in depth here to Kermit Roosevelt. So that’s Theodore Roosevelt. It’s Teddy Roosevelt, his second son. Mm-hmm. So he was had a, had an interesting life and ended up passing away. And we’ll, we’ll dive more into that.

So let’s talk a little bit about more of your trip in, in Anchorage and Captain James Cook. 

Captain James Cook

Jenn: So. When it comes to Captain Cook, I knew a little about him. He’s not as well known in America. As we come to find out, the Australians know him. So he is an explorer from England and he sets out to map in the area, the land areas of the world, and he’s looking for a northwest passage.

That’s what his third voyage is. He does three voyages. The third one is Forst Northwest [00:07:00] passage, and that’s when he discovers Alaska. I wouldn’t say he discovers it. There we’re indigenous people there, but he’s the first person to map it and he’s mapping the coastline and he comes to this inlet, which is now named Cook Inlet and anchors.

Go and sends, he doesn’t go himself, but he sends his first in command to the land to see who’s out there and when and what kind of topography is out there. And because he anchored in that inlet, they named the, the town Anchorage in his honor. And so I, that’s how I basically did his statue. That’s how I basically found it and did the story.

’cause I, I was like, let’s go to the basics. How does Anchorage get its name? Okay, it gets its name from this northwest voyage of Captain Cook back in 1778, and it is the most populated town in a, in Alaska. So it has about 300,000 [00:08:00] people. That’s more than any other town in Alaska. So Anchorage is probably what I would call the.

The Mecca, the where the people are. Yeah. And because they have a huge base there. I mean, the base there is so big. They said if you add all the land area of all the West Coast bases together, it doesn’t even equal the land area of the base in Anchorage, Alaska. And that’s Fort Richardson. Fort Richardson.

Yeah. 

Scott: And, and so. One of the interesting things, right? 

Kermit Roosevelt’s Story and Fort Richardson

Scott: And, and Jen kept telling me before she went, and then while she was there and after she came back, she felt bad that she went without me. I know, because that’s, it’s somewhere that I’ve always wanted to go. And I, I, I had a climbing friend of mine that we had talked about, going to try Denali and, and never ended up doing that, but.

Just the, the scale of Alaska compared to the regular United States and I, I didn’t really have a good grasp for it until you showed me your flight plan. 

Jenn: Yeah, 

Scott: you’re flying from, from Memphis and you made your way to Seattle. [00:09:00] And then from Seattle. Okay. Picture Seattle. In your mind, those listening, it’s another four to five hour flight from Seattle to Anchorage.

That’s how far north you are going and that’s why it’s light at 3:00 AM. 

Jenn: Yeah, and I looked out the window flying across those little islands, as you’re going into Anchorage. ’cause Anchorage is probably like middle Alaska on the south part. And so you’re gonna hit like Juno and Sitka, like you’re gonna fly over all those little island inlets before you hit Anchorage.

And so I’m looking out the window and I had never been here. It is so mountainous and beautiful, and that’s why I was so sad because I knew Scott would love this if you don’t know anything about Scott, Scott is a mountain man at heart and he loves the mountains. He loves to climb, he loves to camp, he loves to hike.

Like those are the things he loves. And. I love him, so I go with him on [00:10:00] some of those things. But this was like. I know this would be what Scott’s dream would be. So when, even when you land in Alaska, the mountains are right there and they’re snow capped and they’re beautiful. And the trees, and we saw moose like walking, like it is, it’s, it’s called the final frontier because it is the final frontier.

And when you think of Anchorage, 300,000 people, it’s the most populated town. There’s all these villages and towns. In Alaska that have, couple thousand people here and there. So it was very interesting to be in this area where it is. It still feels so untapped in so many ways. So. I was like, let’s do the basics.

Captain Cook and the history of Alaska. So in Anchorage, in the south part of Anchorage, they have a statue to Captain Cook. It was put up in 17, in 1976. And it looks like a George Washington [00:11:00] or something. Classic 

Scott: pose, 

Jenn: colonial, right? He has the wig and the curls and colonial dress and he’s looking out to where he, where he was.

Anchored and he was there with the resolution. So he had the two ships with him, the the HMS discovery and the HMS resolution. So he was on the resolution and you get to see him looking out in that area and they have a map of the kind of mountains that you would see out there as well.

And so I went to that. Park told his story. Told the story of what he was looking for. Why is it called Anchorage? What happened when he came, he sent his first ashore. They met about 20 indigenous men warriors, and the British had their rifles and guns with him and to sh as a show of force, they shot one of their dogs to show that they were the stronger group and then traded with them a little bit and then.

Place the English flag, like kinda took said, we [00:12:00] take this land in the name of the British, which is not a new thing for the British to do right. In any means. So, and then from there they realize they keep going north, but they realize there is no northwest passage. They end up going south from there and they make it to Hawaii and that’s where Captain Kirk is gonna be killed.

It’s gonna be some. Miscommunications and some, some tensions in Captain Crickets killed as a result of it. So. Telling that story, I learned more about Captain Cook and what he had done and, and the influence he had. But then afterwards, once we made the video, we had so many people from Australia who they credit Captain Cook with Discovery of Australia, discovery of New Zealand, and so.

They consider him like the Christopher Columbus? Yeah. 

Scott: Someone, someone from Australia actually commented that they were like, and that was something I wasn’t expecting. Mm-hmm. Because once you, if you start dabbling in captain, captain James Cook, history and stuff like [00:13:00] that, you start reading about all, all his travels all over the globe.

It’s pretty incredible what he did and, and where he mapped and, and everything and. A relatively short, span mm-hmm. When he’s sailing around the world. But there was people from Australia saying, yeah, here in Australia, captain James Cook is a big deal. He’s considered the Christopher Columbus, he’s our Christopher Columbus for, for Australia.

Jenn: Yeah. And he I. He leaves on this forage in, in July of 1776. So there’s kinda like a little plaque there that says two big things happened in July of 1776. One is America declares their independence from the British. And another one is a British explorer goes looking for the Northwest passage. And so, and he gets to Australia right around the.

It’s like the summer, the end of 1778, and then he hits Hawaii. He’s killed on Valentine’s Day in 1779. So really interesting. Like one of the last places he’ll go before he hits Hawaii, the end of his life. But if [00:14:00] you hang out in Alaska, what’s interesting is they, oh, they have these flags there and one of them is the British flag.

So they fly the British flag. They, they fly the Alaskan State flag and they fly the American flag, and they really hold on to this. Heritage of Captain Cook being there and planting that flag, and Anchorage being named for it. Another thing I thought was neat that if you’ve ever watched The Amazing Race, they said that season 12 like that was in 2007 and Scott and I haven’t watched much Amazing Race, but we watched that one because.

We were just laughing at the people. 

Scott: Well, and, and we always joke too, that, if we ever got on the Amazing race, everybody would, would be on Team Scott pretty quickly because, just because I’m always the Mr. Cool comment collected. Yeah. And Jen’s emotions are never hidden. And and so we always joked about that.

Oh, it would be so fun if we both got on the amazing race and, and 

Jenn: Yeah. So this statue’s in the finale. Amazing Race. 12. Oh, that’s cool. So they gotta make it, I think they say something like Cook’s Eye [00:15:00] go to where Cook’s Eye was or something like that. And people have to make it to this statue That’s cool.

In Anchorage. So I thought that was neat. So just a little history, like in case you’re ever on one of those races and you’re like, oh, captain Cook, he’s associated with Anchorage, it’s what it’s named for. And he’s the first person to map the coastline of Alaska. 

Scott: Yeah, and and I think one of the interesting thing was, is he never actually stepped foot in Alaska. He sent his folks, they did their thing and I, I can’t imagine they were around for too long. Mm-hmm. And then they took off. They took off looking for the Northwest patches and then eventually, took, made a U-turn and hit, went down to Hawaii.

Now from there. Now see, I think you did this all on the same morning. I 

Jenn: did. I did this morning. 

Scott: And you, so you went out to Fort Richardson, which is what you mentioned, just this massive, massive. Army Base? 

Jenn: Yeah. So it’s, it’s now, it’s kinda like a joint base. Okay. It’s all the services are on this base because [00:16:00] they just, it’s so much space and it’s expansive, so it’s like a joint base.

But I think it was originally an Army Air Force base. And at the time when. Roosevelt is there. It’s an army base, but you gotta think like he’s there in during World War ii. And what’s interesting during World War II is this area is very close to Japan. If you think about the topography and you’re looking at a map, you’re not gonna think Alaska.

Where is it in the world? It’s very close to Japan. So they had a lot of contact with the Japanese for World War ii, and so that’s, it was like the closest American place to Japan. And of course we were fighting with Japan, so that is why he’s out there. He’s, he’s, he of course is Teddy Roosevelt’s son.

He’s in World War I. Remember his brother Quintin has killed in World War I, but for World War ii he FDR sends him out there because he’s [00:17:00] works intel. He’s done military stuff before, but he’s also. Can get mixed in with the wrong group of people and alcoholism, it really is influencing his life. So FDR feels if he can get him away from his in bad influences in New York and get him to a far off place like Alaska where he can do work, where he could be useful maybe those influences won’t have as much impact on his life.

Scott: Yeah, and, and Kermit Roosevelt had an interesting path. So he’s the second of Teddy Roosevelt. So FD second child. Second child. Mm-hmm. Second child of, of Teddy Roosevelt. Franklin, Roosevelt later President, FDR was his cousin. Mm-hmm. So that’s how he ended up coming back.

But not only did you know he served in World War I, but he had this kind of very well known Amazon River, river of doubt. Mm-hmm. Expedition that he did with his father. And you had mentioned. How he actually like preserved his malaria medicine or his mal. [00:18:00] Mm-hmm. ’cause they both caught malaria and then he kinda gave it to his father to make sure his, his father lived.

And he’s credited with kind of like saving his father’s life. 

Jenn: Yeah. So Teddy Roosevelt has a wife named Alice, and if you remember correctly she has one, do they have one daughter Alice, who’s like. The crazy child, Alice is remember Teddy was always like, I gotta handle Alice, right? So his wife dies, I think it’s the same day as his mother.

And I remember he writes, the light has gone out in my life in this diary. So Alice only has one child, and then he marries again Edith Kermit Roosevelt. And so that’s where he has the, the rest of his children with his second wife. And so their first child is Kermit. After her maiden name. Yep.

That’s where he gets the name. And he is for all intents and purposes, a, a presidential son. He goes to Harvard, completes four years of Harvard, and 

Scott: serves in the military. Serves in the military successful businessman. 

[00:19:00]

Roosevelts on the River of Doubt Expedition

Jenn: And after his freshman year at Harvard, that’s when he goes with his father to a safari in Africa.

And in 19 13, 19 14, they do this expedition to South America to explore the river of doubt. And the river has been renamed Rio Roosevelt. One branch is now named Rio Kermit, but it’s on that. Expedition that his father and him both get malaria. Now you can imagine kermit’s younger and so probably more robust and more healthy to fight off the malaria where his father is older.

So even though they’re both. Given rations of the medication to, to beat malaria. He rations his to give to his father and he’s able to beat the malaria because of his, his youth. 

Scott: And he’s 24 

Jenn: and his father meets the medication, but saves his father’s life. So he’s credited with doing that, with being so self-aware and doing that was saving his father’s life.

Kermit Roosevelt and Depression

Scott: Now you mentioned it earlier, but you said, and we talk [00:20:00] about this in the video and that video’s getting ready to come out, that kind of all throughout Kermit’s life, he’s essentially struggled with depression. Mm-hmm. And it sounds I mean, I can imagine at the time when being the, the son of a incredibly popular and successful president, but serving in multiple wars, doing all sorts of crazy stuff.

But he deals with this depression throughout the majority of his life and turns to alcohol after World War I. He’s doing business and he’s doing what Roosevelt’s do. Mm-hmm. Like they, he’s successful. Yeah. He’s, he’s, he’s running successful businesses. Mm-hmm. World War II comes back around.

His cousin’s now president, his cousin, helps him out, I think. Said, brings him in. You said, brings him in, is like major, 

Jenn: a major and, and intelligence officer. Yeah. 

Scott: In the army. 

Jenn: In the, in the army. Because he is, he’s good with these business. He’s, he’s worked with Russia, he’s worked with Finland, like he does global business.

And because he is used to global business, world War II is really about that negotiation and business. And [00:21:00] so because he is so close with Russia, Alaska makes sense. And Russia at the time is a ally. So yeah, he’s, they. He’s goes to Fort Richardson as an intelligence officer to get out from the bad influences of his friends.

And he’s, he’s there for a little while, but he will die of a self-inflicted gunshot wound in June of 19 43, 19 43. So during the middle of the war. Yeah. And. Then they talked to his wife about, would you like to send him back home? She says that his father always said a tree should lie where it falls.

And so she felt he should be buried there with his men where he fell. And so if you visit Fort Richardson, it’s in section A, one of the first graves. This this whole cemetery. Started during World War ii, and it’s on a base, so I had to use my ID to have [00:22:00] access to it. So I don’t know if the public has access to this cemetery, but it was a very easy grave to find.

Kermit Roosevelt’s Gravesite

Jenn: But it was so cold. Yeah, you looked 

Scott: pretty cold out there. Your nose was red. 

Jenn: It was. And, but it was, it was very easy to find and they, the graves were your typical white. Marble gravestones for a national cemetery. But what I also found interesting about this, this area was during World War ii, they had some Japanese that were killed during some fighting, and the bodies, they buried the pri the prisoner or the, the captured or the dead Japanese in.

Fort Richardson National Cemetery, they buried them there and it wasn’t until more recently, they disinterred them and burned their bodies in more customs to their religion to release their souls. And then. Put their ashes back and then they have a Japanese monument to them. So I found that for you as well, so you can see that.

Scott: [00:23:00] Yeah. In, in the part of the thing that I gave Jen a hard time is I wish I could have been there just, just to take B roll because the, the video was just astounding. Here I am trying to focus on, on Jen’s face as she’s talking, but the scenery behind her with the mountains and the trees, it was just.

Absolutely stunning. So here’s this national cemetery on the base with the Alaskan wilderness, right behind her, it’s a, it, it was just absolutely gorgeous. Yeah, it was, it was pretty cool. 

Jenn: The cemetery feels like it’s just in the middle of the Alaskan wilderness. And what’s interesting is, I’ve been to Quentin.

Roosevelt’s grave because he is buried beside Theodore Jr. In the American Normandy Cemetery. His body was moved to be beside his brother ’cause he dies in World War I. And theore Roosevelt Jr. Dies in World War ii and here is another brother who dies in World War II and his grave. So they, they’re basically where they fell during their service.

And so I thought that was very, [00:24:00] I don’t know, honorable of the Roosevelt. Boys and of Teddy Roosevelt, he gave three sons to the war. When you think about this as a president, he gave three sons to American Wars and I was able to visit three their graves. So it was really neat. It was important for me to go there.

I think Kermit Roosevelt is probably the more famous of all the graves in that cemetery, but it is a very it was very honorable to go there and to be in a national cemetery. I was the only person there. So when you’re in Alaska, like when you think about it, a a town of 300,000. How many people are on the base.

Yeah, and then how many people like I, even when I drove there, I was like the only car for a long time. So it’s one of those places that you’ve really have got to be self-sufficient because if something happens, like you’re saving yourself. So I just made me really feel like if you want that kind of adventure, that last frontier, that, explorer mentality.

[00:25:00] Alaska is that place. I really felt that there. 

Scott: Yeah. No, it was, it was beautiful. 

Conclusion and Reflections

Scott: I encourage you guys, I’ll, I’ll link the videos down below. But, look into, I’m, I think there’s plenty of books about Captain James Cook. In fact, I think I’m gonna pick some up myself. But the learning about the Roosevelts and kind of what Teddy Roosevelt’s Sons did is, is been pretty fascinating.

It was cool that you got to go. Visit Kermit because here you are visiting Kermit in Alaska, then the other brothers all the way in France at Normandy. So it’s pretty wild where our opportunities have been able to get you to explore some of the history out there. 

Jenn: Yeah, I’m very honored. I’m very honored to tell their story.

I mean, when you think of the Roosevelts, that is quintessential American Dynasty right there, and so to be able to visit the the sons that have served of that family, it really was an honor for me. 

Scott: Yeah, no, it was beautiful. Again, I’ll, I’ll link it down below. For those listening for our audience, if you guys wanna support the podcast, you can go to talk with history.com.

There’s a support link down below. If you wanna leave us a tip, buy me a coffee, buy us a sandwich, [00:26:00] buy us some gas money. Or if you want a little bit more resources, you can go to the history road trip.com. I try to send out a newsletter occasionally. Try to include some maps, links to the locations where we visit.

If you guys ever want to go visit these spots themselves, you can get a little bit more resources there. But thank you. So thank you so much for listening, and we’ll talk to you next time. 

Jenn: Thank you. 

​ [00:27:00]

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