The Daily Stoic - What a 9/11 Pilot Will Never Forget | General Dan Caine (BONUS)

Episode Date: September 11, 2025

In today’s bonus episode, Gen. Dan Caine reflects on being one of the first pilots in the air on 9/11 and what that moment taught him about courage, leadership, and service.General Dan Caine is the 22nd Chairman of the Joint Chiefs of Staff. He has flown more than 100 combat hours in F-16 aircraft. His total flight hours are 2,800. Throughout his career he was awarded the Defense Superior Service Medal, Distinguished Flying Cross, Bronze Star Medal with bronze oak leaf cluster and the Defense Meritorious Service Medal. 💡 Want more insights from extraordinary leaders like General Caine? Check out The Daily Stoic Leadership Challenge at store.dailystoic.com.👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic Podcast, where each day we bring you a stoic-inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women to help you learn from them. to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visitdailysteoic.com. I wanted to start with 9-11. You know, we've talked to a bunch of a bunch of of interesting leaders and they've been through some crises and difficulties, but nothing quite

like being one of the first planes in the sky on 9-11. So could you maybe walk us through that day and what that was like? Of course. On September 11, 2001, I was actually stationed here in Washington, D.C. out at Andrews Air Force Base. I was flying F-16s. I'd been to the Air Force top gun school where we don't play much volleyball. We mostly focus on getting better as tacticians with a little bit of jest towards my Navy brothers and sisters. And, you know, we had just gotten back as a squadron from out in Las Vegas in Ellis Air Force Base where we were getting ready to deploy.

And, you know, that Tuesday here in Washington was a beautiful and gorgeous day. And I was not scheduled to fly that day. I was originally sort of running the flying operation for the squadron as the chief instructor and tactician. As we came in that morning, we obviously had no idea what we were going to face. And we were in a meeting at the squadron, just a training meeting when one of our young intelligence professionals came in and said an airplane has just hit the World Trade Center. And of course, my first thought was it's a small civilian airplane. This couldn't be. And as you get older, as leaders, you start to develop that spidey sense of just

something's not right. And I felt that got up, walked into our squadron lounge where we had a big flat screen TV. And remember, I still get chills today even. remember clearly the helicopter news shot showing the first tower burning when the second airplane flew into the picture and hit hit the building silence could have heard a pin drop and we sat there for what seemed like a long time which was probably just a very few seconds and I went to the desk where we had all of our communications gear and I picked up the phone and called the Secret Service and said, I don't know what's going on.

What do you need us to do? We had a relationship with the Secret Service in Washington because we flew out of the same airfield as the president. The next phone call was the White House saying, get anything you can airborne. The nation is under attack. And right at that point in time, my. boss, Brigadier General Dave Worley, walked in and I handed him the phone. And I said, hey, sir, this is, this is for you. And we went and got ready to fly. And I was myself and a wingman. And there were two

other folks as well. And we got our gear on and went running back to the ops desk and met General Worley. General Worley read us the rules of engagement for defending the national command of authority. It was very liberal and it was on us. And, you know, when you think about leadership for the folks on the on the call and on the video here, I will never forget what then General Worley said to us. He's just read us the rules of engagement, which are extremely liberal. The decision is clearly mine. It's the cap commander, the mission commander over the combat air patrol. And he reads us verbatim. And then he pauses and he looks at us and says, hey, Dan, look. I don't know what you're going to face out there.

I think you're probably going to have to make some very difficult decisions, but here's what I want you to know. I trust you, you're going to do the right thing, and no matter what, I have your back. And you want to talk about saying the exact, exact right thing at the exact right moment. We ran to the jets and scrambled and, you know, we're flying that morning. we took off, I think, right around the same time that the real heroes or some of the real heroes of that day, the passengers of Flight 93 were assaulting inside the airplane, knowing full well what they were facing, knowing what had happened in New York City, and yet finding the courage to step up, not having taken the same oath that we take to uphold and defend the Constitution, but knowing that their nation union to do something. And so flew the rest of that day and a lot of intercepts and a lot of sort of keeping airplanes away from downtown Washington.

And our squadron flew for the next 45 days after that. And I deployed pretty quickly overseas to start fighting al-Qaeda. Well, to bring all that together, I think there's a couple interesting themes. So one, which is open lines of communication. I think it's pretty incredible that you're just sort of. of very quickly on the phone with the White House. I was reading a book about Admiral Rickover recently. They just sort of mentioned it offhandedly. But I guess for maybe it's still the case, but it was the case during the Cold War, that every commander of a nuclear submarine

could directly call the White House. Like there was just a phone they could pick up. And it would ring at the president's desk. And so I think sometimes we think these organizations are huge. There's this massive chain of command, but at the top, it sounds like... Well, we didn't call... They called us, just to be clear, you know, I called the Secret Service. But that's what I mean. That's what I mean. Yeah, yeah, yeah.

Is that at the end of the day, the really elite operators have to be completely flat. There has to be open lines of communication and flexibility there. And flatness is something from a leadership perspective that we value greatly. certainly I value greatly. And I drive the organizations that I've blessed to lead or be a part of towards that flatness. I think as leaders, if we don't understand what is happening at the edge of the empires that we're blessed to lead, serve, and help with, then we can't possibly understand what's really going on it. So flatness is a key to that. Yeah, because often, you know, I think especially at the lower levels, you can be like, well, I pass this up the chain and something will happen.

But I think it's interesting that you called the Secret Service. You didn't sort of wait around and say, let's see if somebody needs me. Let's wait to see where this goes. You sort of use the contacts you had on that day to sort of say, you know, what do you need for me? What can I contribute? What's going on? I think we've got a responsibility as leaders at whatever level you're leading at. proactive and not reactive, to realize when there's a white space and lead your organization or yourself towards that white space to improve the overall effectiveness, efficiency, combat, whatever kind of organization you're leading, and move towards the problem. are here, and they're newly designed to help you do more faster.

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deed.com slash daily stoic terms and conditions apply hiring deed is all you need. When that goes to the passengers on flight 93, which you texted me a transcript of that call on 9-11, which it always sort of gives you the chills to read. I think the idea that, yeah, they weren't sort of technically leaders in any way. It was, you know, a handful of people, talking on, you know, phones on airplanes, which I think younger people don't even remember was a thing, that you could swipe your card and get a handset out of the back of a seat. But they sort of anointed themselves, leaders. And it was, I thought it was remarkable as that you had this 911 operator relaying information from all over the world, sort of that all these people involved,

although they had no official authority or even official obligation to do anything took it upon themselves to say like, look, we might not be able to solve this thing, but we can not contribute to the problem. We can not make this tragic event more tragic. And we're going to try to do something. And I, you know, I just, I think about them every day, right? And that is real courage, knowing what is going on in the United States at that point in time and having the intestinal fortitude, the bravery to stand up and go forward knowing it's just an incredible example. You know, America started to fight back immediately and they were the first steps, the firefighters that headed up building for the first steps, you know, the people at the Pentagon

were the first steps. And out of this tragedy of September 11th, we can find incredible goodness on who we really are as a country. And I hope we just always take advantage of those examples moving forward. Yeah, you know, it's almost easy to celebrate the firefighters and the police officers, but there were also the office managers and the employees and the people who had, you know, they worked in this enormous office together, but it never met before. And again, had no real obligation to anyone but themselves and decided, hey, I'm not leaving anyone behind or, hey, I'm going to do what I can here. That is also what leadership. Leadership isn't this thing you get promoted to necessarily. It's also what you do in moments of crisis. Absolutely. Absolutely.

It could have been a lot worse that day. Those people not evacuated the towers and those people stood in the stairwells and helped other people get down there, people in the Pentagon could have been a lot worse. Or that plane, you know, Flight 93 could have crashed into the White House or the Capitol building? It would have been much worse. And then when I think about leadership, although thankfully you didn't have to, it strikes me that what your commander was talking about was the idea that within

the latitude that you had been given, you would have, you potentially would have to make some very hard decisions in the moment, which is also, you know, something we've talked about, but sort of the definition of leadership to me is, you know, can you make hard decisions with limited information and limited time? Yeah, you know, and as I reflected on that day, and look, we just did our jobs. We just did our jobs. And thankfully, we didn't have to make the decision to shoot somebody down. As I reflected back on that day and folks, have asked me, you know, were you scared or what was going through your mind and whatnot? I mean, of course, but overwhelmingly the thing that, and I'm grateful for this experience in

some ways as a leader, my largest concern was not to miss somebody and not to, and not to be able to prevent or be unable to prevent an airplane going into the White House, going into the capital. And that drove everything. And as I didn't realize it at the time, I was younger and a young captain, but as I've reflected on that over the years, I'm grateful for that and other situations like that where I built some trust and confidence in my own instincts as a leader to be able to make difficult and complex decisions with limited information. in short amounts of time. And that is something that I've learned to value greatly.

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