Happy Hour: Bret Baier’s Teddy Roosevelt Adventure

Summary

Podcast Summary: Kennedy Saves the World Episode: Happy Hour: Bret Baier’s Teddy Roosevelt Adventure
Date: October 24, 2025
Host: Kennedy
Guest: Bret Baier (Anchor, Author of "To Rescue the American Spirit: Teddy Roosevelt and the Birth of a Superpower")

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Episode Overview

This lively episode features a spirited conversation over drinks between Kennedy and Fox News anchor/author Bret Baier, centered around his new book on Theodore Roosevelt. The discussion weaves together Roosevelt’s maverick political energy, outsized personality, impact on American history, media savvy, and enduring relevance in today’s political landscape. With wit and personal anecdotes, the pair delve into historical parallels, lessons for modern America, and Baier’s writing experiences.

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Key Discussion Points & Insights

1. Why Teddy Roosevelt?

• Inspiration to Write About Roosevelt
  Baier explains that Roosevelt's vivid life, “jumps off the page,” and is rich with dynamic anecdotes and crucial American history ([00:49]).
  • “Historians look at him as one of the top four [presidents] … Lincoln, Washington, FDR and Teddy Roosevelt.” – Baier [00:52]
  • The Roosevelt family background created two political branches: Republican Teddy and Democrat FDR ([01:22]).
  • Roosevelt was a notorious party "troublemaker" in New York politics, forcing reforms and fighting corruption ([01:42]).

2. An Unlikely President

• Roosevelt was shunted into the vice presidency to contain his disruptive energy, only to become the youngest president at 42 after McKinley’s assassination ([02:19]-[03:16]).
• “He thinks this is going to be boring [...] Then obviously, six months in, William McKinley gets assassinated …” – Baier [02:36]
• Kennedy draws a parallel: despite improbability, Roosevelt was exceptionally qualified: military, politics, science ([03:16]-[03:52]).

3. Comparing Roosevelt’s Experience

• Kennedy asks about Kamala Harris’s claim of being “the most qualified ever to run for president,” questioning how modern resumes stack up to Roosevelt ([03:16]).
• Baier jokes, sipping his drink, suggesting Roosevelt’s qualifications were far more substantial ([03:52]).
• Discussion of Roosevelt's press savvy and his similarity to Donald Trump as a media figure ([03:52]-[04:29]).

4. Military Bravado and the Rough Riders

• Transition from Assistant Secretary of the Navy to leading the volunteer Rough Riders in the Spanish-American War ([04:29]-[05:50]).
  • “He recruits these guys… [forming] this Star Wars bar of fighters that he calls the Rough Riders.” – Baier [05:13]
  • Ingeniously included journalists for positive coverage: “He puts them on his boat... that's really how you get all of the in-depth stories of the Rough Riders.” – Baier [05:51]

5. Roosevelt’s Charisma and Tough Upbringing

• Social media would suit Roosevelt’s persona: “He was larger than life then.” – Baier [06:33]
• He overcame childhood frailty through grueling and sometimes bizarre “cures” (like cigars and coffee).
• “What ended up working is outdoors … he becomes really a scientist.” – Baier [07:29]
• Family stories: collecting birds and sharing a room with his brother, who protested the dead bird entrails ([08:04]).

6. Race, Statues, and Historical Memory

• Kennedy asks about the removal of Roosevelt’s statue from the American Museum of Natural History ([08:18]).
• Baier regarding the statue: “I think so. He was a significant figure and … was a reason why some of that stuff was there.” [08:42]

7. Roosevelt’s Foreign Policy and Making America a Superpower

• Roosevelt’s presidency coincided with America shedding Civil War aftershocks and rising as a global power ([09:12]).
• Orchestrated the peace between Russia and Japan (Portsmouth Treaty), earning a Nobel Peace Prize ([09:29]).
• Notable Kennedy quip: “Maybe make America great again.” – Kennedy [09:10].

8. Parallels to Today: Trump and Foreign Policy

• Kennedy inquires about similarities between Roosevelt and Trump, especially as a "peacemaker" ([10:34]).
• Baier: “It's not one to one, but there are a lot of similarities,” highlighting their showmanship and ambition for global impact ([10:50]).
• Discussed Trump’s ongoing efforts for peace deals and potential future Nobel Prize ([11:26]).

9. Writing History in Tumultuous Times

• Baier reflects on the challenge of writing history books as current events reshape their context in real time ([12:14]).
  • “I remind people that we've been in really dark places in our country before, where we've been fractured and yet we've managed to get through.” – Baier [12:14]
• The cyclical nature of American challenges: "finding these nuggets of history… helps us know where we’ve been and often where we're going to go.” – Baier [13:02]

10. Roosevelt’s ‘Strenuous Life’ and Modern Parenting

• Kennedy: “Do you think that the strenuous life is more emblematic [than the Man in the Arena speech]?” ([13:17])
• Baier agrees, linking Roosevelt’s philosophy to his upbringing and urging people to “get in the game” and “make a consequence of your life.” ([13:31])
  • “Don’t throw grenades from the outside. Get in the game, be somebody in the game, and make a consequence of your life.” – Baier [14:01]

11. 2028 Election Speculation

• Kennedy rapid-fire asks Baier who he predicts for next president (Newsom, AOC, JD Vance, Pete Hegseth, Marco Rubio) ([14:01]).
• Baier: “I think J.D. Vance has the inside race right now… every time President Trump talks about it, he mentions Marco Rubio … I don't think he's fully decided.” ([14:15])
• Baier describes the volatility in upcoming elections and the influence of congressional outcomes ([14:49]).

12. Writing History vs. Living in the Present

• Kennedy: “What is more fascinating for you… history or the present moment?” ([15:08])
• Baier: “The day to day is probably where the focus is because it's like drinking from a fire hose… But the history stuff helps inform the day to day.” ([15:40])

13. Doris Kearns Goodwin’s Endorsement

• Baier shares pride in receiving a blurb from historian Doris Kearns Goodwin, his “white whale” for book endorsements ([16:14]).

14. Given the Choice: Which President to Cover?

• Kennedy: “If you could have been a reporter in any administration, which would you choose?” ([16:36])
• Baier: Covering Roosevelt “would have been a blast because the guy knew how to make a headline.” ([16:44])

15. The Legendary Milwaukee Assassination Attempt

• Roosevelt survives being shot in the chest, delivers a 45-minute speech bleeding on stage ([17:28]-[17:55]).
  • “He says, ‘I have just been shot, but I want to talk to you more.’ And it continues on for 45 minutes.” – Baier [17:55]
• Roosevelt loses the election as a third-party candidate, paving the way for Wilson ([18:19]).

16. Book Recommendations and Closing Banter

• Kennedy recommends Baier’s book as a holiday gift and jokes about “a little TR in the stocking” ([18:33]-[19:07]).
• Baier plugs collecting all his presidential biographies, “frosted and served” for history-loving readers.

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Notable Quotes & Memorable Moments

• “He thinks this is going to be boring. I'm just going to go around the country delivering speeches. And then obviously six months in, William McKinley gets assassinated...”
  – Baier [02:36]
• “He recruits these guys… [forming] this Star Wars bar of fighters that he calls the Rough Riders.”
  – Baier [05:13]
• “Don’t throw grenades from the outside. Get in the game, be somebody in the game, and make a consequence of your life.”
  – Baier [14:01]
• “He says, ‘I have just been shot, but I want to talk to you more.’”
  – Baier [17:55]
• “But the history stuff helps inform the day to day. Like if you can look back at history and say, oh, look at this. Here's perspective from 30,000ft.”
  – Baier [15:40]
• “Maybe make America great again.”
  – Kennedy [09:10]

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Timestamps of Important Segments

| Segment/Topic | Timestamp | |:-------------------------------------------|:-----------:| | Introduction and book launch | [00:10] | | Roosevelt's background, family, and ascent | [00:42]-[03:16] | | Roosevelt vs. Modern Politicians | [03:16]-[03:52] | | Spanish-American War/Rough Riders | [04:29]-[06:12] | | Roosevelt’s childhood and outdoors life | [06:33]-[08:06] | | Museum statue debate and significance | [08:18]-[09:10] | | U.S. foreign policy turn, Nobel Prize | [09:29]-[10:11] | | Roosevelt/Trump comparisons | [10:34]-[11:26] | | Writing history amid current events | [12:14]-[13:02] | | Strenuous Life and parenting | [13:17]-[14:01] | | 2028 election predictions | [14:15]-[15:08] | | History vs. present for Baier | [15:40] | | Doris Kearns Goodwin story | [16:14] | | Covering presidents as a reporter | [16:44] | | Milwaukee assassination attempt | [17:28]-[17:55] | | Book recommendations and closing | [18:33]-[19:07] |

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Tone and Language

The conversation is lighthearted, witty, and conversational, mixing deep historical insight with banter, drink clinks, and humor. Kennedy’s irreverent curiosity pairs well with Baier’s enthusiasm for presidential history and knack for explaining complexities in an inviting, readable way.

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A must-listen for history buffs, modern politics watchers, and anyone interested in the wild, inspiring saga of Theodore Roosevelt—and the lessons he left for today’s America.

Transcript

[A]

Hello and welcome to this episode of Kennedy Saves the World. Bret Baier Saves America every night on Special Report at 6:00pm Eastern. Three in the West, Brett is here. He's got his brand new book to rescue the American spirit, Teddy Roosevelt and the Birth of a Superpower. Great book, obviously, as usual. Brett Baer, welcome back to Community Saves the World and cheers to you.

[B]

Cheers. Love it. This is delicious.

[A]

Mmm. Oh, yeah.

[B]

Yeah, it's refreshing. All day long like this.

[A]

How long have you been waiting to write about Roosevelt and where does he stand in your pantheon of presidents?

[B]

So Teddy Roosevelt, as you know, jumps off the page. All the anecdotes about him are as rich as you would remember. But when you get into history, these nuggets of history, it's really fun. I think, you know, historians look at him as one of the top four. It's usually Lincoln, Washington, FDR and Teddy Roosevelt. And the fact that the cousins are in even the top list is really something considering that the Roosevelt family, both of them considered politics as kind of dirty business and should move into it.

[A]

Well, it was in New York, especially leading up to the presidency, which was an improbable position that he was in. But what I didn't know until I read your book was that there were two distinct branches of the Roosevelt clan. There was the Republican version, the Teddy Roosevelt version, and then the FDR Democrats.

[B]

Yeah. And it was much different. And while they communicated, they didn't really hang out, were two separate branches. Teddy Roosevelt is an interesting figure. He is a troublemaker for the party. He is not a guy that goes along to get along. He stirs up the pot to the point where, you know, when he's New York governor, he's pushing things. When he's New York police commissioner, he's trying to clean up the corruption and.

[A]

The party says, but also let people drink on Sundays.

[B]

That too. And, and cheers to that.

[A]

Amen. To Teddy.

[B]

And to Teddy.

[A]

And imbibing whenever you choose.

[B]

And basically the party, when he's New York governor says, we've got to do something with this guy. And they say, let's make him vice president because we can put him in this box and just leave.

[A]

He'll never get out of it. Like that's, that's the last we'll hear of Theodore Roosevelt.

[B]

And he, he thinks this is going to be boring. I'm going to, just going to go around the country delivering speeches. And then obviously six months in, William McKinley gets assassinated in Buffalo, New York, gets shot, and Teddy Roosevelt goes and sees him. The Doctors say, you know what? He. He's probably going to survive.

[A]

You're good, you're good. Go back to vacation, life is normal.

[B]

And he goes back to the Adirondacks and goes hiking. And then McKinley turns for the worse, and they have to find him in the mountains. And it's this harrowing journey for him to get Back to Buffalo, New York. He becomes president. The youngest president ever at 42 years old.

[A]

Wow. But he was ready. I mean, I was thinking about this as I was reading the different phases of his political life and his professional life, and he was very qualified to be president. Kamala Harris said recently at a stop for her book, 107 Days, that some are saying that she is the most qualified person to have ever run for president. Would you put her resume against someone like Theodore Roosevelt and then say that their qualifications are pretty equal?

[B]

I mean, this drink is wonderful. Really is. Some are saying, we have not found the sum. No, he was very qualified for the moment. He also knew how to operate in the moment. He knew how to control the press. He knew how to make the story. He was a lot similar to a certain president that we have currently who, you know, sucks up the oxygen in the room every day and is in the front pages. You know, that starts when he goes to. He's Assistant Secretary of the Navy. He resigns because he wants.

[A]

That was awesome.

[B]

He wants to get involved in the Spanish American War.

[A]

An Army Rough Rider, which was, you know, the nickname for their volunteer cavalry division where he was lieutenant colonel. But when I read that, so I was. I was reading the book, I was like, oh, Secretary of the Navy. That's cool. Navy guy. And then I was like, wait a second. The Rough Riders aren't the Navy. The Navy doesn't go around riding things. They. They swim and float around in boats. And then I realized, like, three of the most consequential presidents in our nation's history are army guys. So obviously, the two West Pointers, Ulysses S. Grant and Dwight Eisenhower. Ike. And then in the middle is Teddy Roosevelt. Yeah. What does that say about that branch of the armed forces?

[B]

There you go. Well, they definitely roll up their sleeves and get it done. He recruits these guys. He's been out in North Dakota. He's been with these cowboys and kind of ruffians and gets some of them. Then he gets the guys that he was with in Harvard who want to serve, and he puts together this Star wars bar of fighters that he calls the Rough Riders. They eventually get along. They go down to Florida, they commandeer a boat to get over to Cuba. And while he's doing that, he realizes that the New York Times reporters don't have a ride over to Cuba and he puts them on his boat.

[A]

Stop it.

[B]

And that's really how you get all of the in depth stories of the Rough Riders is because he had his own press pool essentially with him in these very heroic moments. Now, I'm not saying there wasn't heroism and there wasn't just real drama, but the reporters are with them to document it all. And that's why he comes.

[A]

To amplify a hero. Yes. And they were like, you totally have to be governor. Like, this is amazing. And he's like, don't mind if I do.

[B]

Yeah.

[A]

So, you know, you write that he, he was such a forward leaning, physical, charismatic person that he would have been perfect in this era of social media.

[B]

He would have. I mean, a lot of people would have followed Eddy Roosevelt. I think no matter what he was doing, I really do think he would have been a big figure. And he was larger than life then. And the funny part is he was such a weak and sickly kid because of asthma that his parents didn't think he couldn't get out of bed. They tried everything to solve his asthma. Weird remedies like cigars and black coffee.

[A]

So when I, when I, when I read about that, it was like, well, you know, we gotta provoke the asthma. You know, we gotta toughen the kid up.

[B]

Poison it out of him.

[A]

Yes, exactly. And do stuff that really makes him absolutely miserable. When you were researching this and you found out about the cigars and black coffee, did you look at your own parenting and say, yeah, maybe I'm not doing enough to really jostle my boys.

[B]

Son, please try the cigar. No. They were really aggressive. What ended up working is outdoors. And that's why he becomes this outdoorsman. He collects species and all kinds of birds, and he becomes really a scientist. That's what he thought he was going to be as a botanist scientist. Writes a lot of books about that. And it's his love, his brother Elliot. When they traveled overseas to Europe, he was his roommate. And Elliot goes to the father and says, dad, I need my own room.

[A]

I can't do the thing with the dead birds. I can't do it.

[B]

The father says, why do you need your own room? And he walks down the hall and there are all these birds. There are like entrails in the tub. And yeah. He says, all right, Elliot, you can.

[A]

Have your own room. Yeah, that was like Alexander the Great he would collect specimens and send them back to Aristotle and just go, science. So, you know, in our modern era, Theodore Roosevelt is most famous for having his statue taken down at the American Museum of Natural History. Is that, was he aggrieved?

[B]

I think so. I mean, I think so. He was a significant figure and, you know, was a, was a reason why some of that stuff was there. So, yeah, I think so. Listen, I think history is going to look back and does at Teddy Roosevelt as a really significant figure. And in part, this is about his effort to make America a forward leading figure in the world.

[A]

Maybe make America great again.

[B]

Maybe make America great.

[A]

But we're, I mean, at this point, a lot of people think there's a big difference between when his presidency started and the end of the Civil War. But we were still very much living in the fractured turmoil, the fallout of the Civil War at the turn of the century, weren't we?

[B]

100%. I mean, the reconstruction and all of the fallout from that still lingers. And the world is not looking at us as a leader as of yet. It's really his presidency that starts to focus our thought about being a leader elsewhere. Russia and Japan are fighting over territory. He decides to do the logistics and get both of the leaders to Portsmouth, New Hampshire, and creates this peace, peace deal where it takes a while, but because of Teddy Roosevelt, they don't go to war. Russia and Japan, they figure out a peace deal and the rest of the world says, wait a second. America is something.

[A]

Yeah, there is something to this. There's something to this American experiment. Don't go anywhere more Kennedy saves the World right after this.

[C]

It's will taint country. Watch it live at noon Eastern Monday through [e-mail] or on the Fox News YouTube channel. And don't miss the show. Listen and follow the podcast five days a week at Fox News Podcast or wherever you download your favorite podcasts.

[A]

So in researching this book and watching the second Trump administration unfold at a rapid pace that I don't think anyone could have anticipated, is Theodore Roosevelt the most similar president to Trump?

[B]

It's a great question. It's not one to one, but there are a lot of similarities and the hunger to be the peacemaker. I think you're seeing real time in President Trump 2.0 in the second administration. Clearly, you know, he sees himself as that role. He's now at seven, you know, he says, and hoping for eight with Russia, Ukraine, that one's becoming a little tough. But Teddy Roosevelt does get the Nobel Peace Prize. For Russia, Japan negotiations. And. And I think President Trump, you know, thinks he should as well.

[A]

Do you think he will?

[B]

I bet he does next year.

[A]

Do you think? So John Fetterman said that if he achieves this Gaza peace deal, and also if there is, you know, some sort of peace deal between Russia and Ukraine, then he should get the peace prize.

[B]

Yeah. But I mean, you look at Pakistan, India, you look at Azerbaijan, Armenia, you look at the Congo in Rwanda, I mean, those are big things that have been happening for decades. And, you know, any one of those things could have triggered a nomination and.

[A]

Defined a president's foreign policy.

[B]

Yeah.

[A]

I mean, that's why it's hard to comprehend what is going on this quickly with the Trump administration. And, you know, obviously, where you were when you were writing the book is very different than where we are now as the book is coming out.

[B]

100%.

[A]

Yeah.

[B]

And so usually on these books, I wait until the very end to write the intro and the epilogue, because something has happened that is directly in correlation to this book in some way, shape or form, and it's happened pretty much every book that I've written, like Grant, was January 6th, you know, and all of that happens. And I remind people that we've been in really dark places in our country before, where we've been fractured and yet we've managed to get through.

[A]

Yeah. And it is because of the history that we have, that informs are present, that allows us to take a deep breath, take a step back, and know that, you know, there will more than likely be a tomorrow where we can lean in and exceed what we've already accomplished.

[B]

Yeah. And I think that's part of this whole process is like finding these nuggets of history that tell a story that is very readable, but it helps us know where we've been and oftentimes where we're going to go.

[A]

Because.

[B]

Because it's cyclical.

[A]

So Roosevelt is often defined by his man in the arena speech, but do you think that the strenuous life is more emblematic of who he was and the lessons that we can internalize, especially as parents?

[B]

Yeah, I think the strenuous life is a direct result of his upbringing. His father really pushing him, saying, you gotta get strong, you gotta get in the game. And that leads him to, after his presidency, delivering that citizenship speech that eventually becomes the man in the arena, which is, don't throw grenades from the outside. Get in the game, Be somebody in the game and make a consequence of your life.

[A]

Who do you think is more likely to be president in 2028, Gavin Newsom, AOC JD Vance or Pete Hickseth Marco Rubio.

[B]

I mean, I think J.D. vance has the inside race right now. You know, like he's obviously leading the money game and is in position. I will say that every time President Trump talks about it, he mentions Marco Rubio and he says Marco Rubio either first or second. It's interesting. I don't think he's fully decided, but I think how President Trump decides will make a big difference in who is at least on that side. There's, I think a lot can happen between now and 28 and the 26 election if one of the Houses goes to the Democrats and it would probably be the House of Representatives. That would be a springboard to be able to say, here's the look forward. I think it's still tough. It's still up in the air. It's gonna be nip and tuck.

[A]

So what is more fascinating for you? Our history. Because you are a historian, whether you like it or not, you write books, you do a lot of deep research about past presidencies. And obviously as readers, we learn new stories. We're on a different journey with every president that you write, write a biography about. Or is it the present moment that we're in and the fact that there are so many variables at this moment in time that we really don't know how things are gonna turn out?

[B]

Yeah. So the day to day is probably where the focus is because it's like drinking from a fire hose. Every day is something totally new. Probably five different leads.

[A]

And yet we're still dehydrated of the.

[B]

Show and we should drink more. But the history stuff helps inform the day to day. Like if you can look back at history and say, oh, look at this. Here's perspective from 30,000ft. Speaking of historians, this is the number one that I wanted to get on all of the books. Doris Kearns, Goodwill.

[A]

Yes, I saw that.

[B]

It's the white whale of blurbs. And she did it and she read it and she. And I was really proud to get her blurb.

[A]

Have you tried to get blurbed by her in the past?

[B]

I have. It's a tough one to, you know, get. She loves the books. She doesn't have time. She's doing her own thing. She read this book and she was really, really gracious to give me that.

[A]

Yeah, that's awesome. If you could have been, at any moment in history, been a reporter of any of these administrations, which one do you think would have been the most satisfying?

[B]

That's so good. That's such a good question. You know, the first book that I wrote about Eisenhower was a fascinating time and a character that was not appreciated at the time. Each one of these presidents, you know, you look at Grant, you look at Reagan, really wasn't fully appreciated at the time. I think obviously he had star power. I would say covering Teddy Roosevelt would been a. Would have been a blast because the guy knew how to make a headline.

[A]

Yeah. And you're an active outdoorsman.

[B]

Yeah, I could hang.

[A]

Absolutely. He's like if Ernest Hemingway were president.

[B]

Yeah. But think about the speech he delivers when he's in the Bull Moose party and an assassin tries to take him.

[A]

Out in Milwaukee in Wisconsin. Exactly right.

[B]

The bullet gets hit. Hits the eyeglass case in a speech that's 50 pages long. And it gets into his chest enough that the shirt is all bloody. And he pulls open and he says, I have just been shot, but I want to talk to you more. And it continues on for 45 minutes.

[A]

Now.

[B]

The bullet has not gone all the way through, but it's gone into him, and he's still speaking from the back in Milwaukee. And I mean, that's a character.

[A]

Yeah. But that's also a reminiscent of fight, fight, fight.

[B]

Right.

[A]

It's like, I will not be brought down by this. This is not fatal to my physical body or to my presidency or my legacy.

[B]

Yeah. And that's how important I think you are. As I'm going to continue to. You know, he ends up losing. He ends up getting the most votes of any third party and probably, well, definitely leads the. Opens the door to Woodrow Wilson, which caused all kinds of issues.

[A]

Yeah. We have to shake our heads at that. But this is a wonderful read and dare I say, a great Thanksgiving present.

[B]

Oh, yes.

[A]

Or even Christmas in Hanukkah coming around the corner. And a little TR on the stocking. That'd be a mighty nice gift.

[B]

Could be. And you could get all the two rescues to rescue the Republic, to rescue the Constitution, to rescue the American spirit. Imagine that stocking stuff.

[A]

No, that would. That would be a nice addition to the library right there. Just a slice of history, frosted and served by the one and only Brett Baer.

[B]

Thank you so much. Delicious. Report is going to be a lot better today.

[A]

It's going to be very special. This has been Kennedy Saves the World. Along with Bret Baier. I'm Kennedy. Listen ad free with a Fox News podcast plus subscription on Apple podcast and Amazon prime. Members can listen to this show ad free on the Amazon Music app. Oh, go ahead and leave me a review while you're there. I'd love to hear what you have to say. You've been listening to Kennedy Saves the World on the Fox News Podcast Network.