BONUS | What a 9/11 Pilot Will Never Forget (with General Dan Caine)
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What sparked the conversation about 9/11 with General Dan Caine?
Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. I wanted to start with with nine eleven. You know, we've talked to a bunch 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 nine eleven. So could you maybe walk us through that day and what that was like?
Of course. On September eleventh, two thousand and one, I was actually stationed here in Washington, DC, out at Andrews Air Force Base. Um, I I was flying F-16s. I I'd been to the Air Forces Top Gun School where we don't play much volleyball. We mostly focus on on getting better as tacticians with a a little bit of jest towards my Navy brothers. And uh, you know, we had just gotten back as a squadron from out in Las Vegas, uh, an 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 uh I was not scheduled to fly that day. I was originally sort of running the flying operation for for the squadron as the chief instructor and tactician.
You know, as we came in that morning, we obviously had had no idea what we were gonna face. And we were in a meeting at the squadron, just a a training meeting when one of our young intelligence professionals came in and said, an airplane has 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 uh as you get older as leaders, you start to develop that spidey sense of just something's not right. And I I felt that got up, walked into our our squadron lounge where we had a a big flat screen TV. And uh and remember s I still get chills uh today even. Remember clearly the helicopter news shot showing the first Tower burning. when uh when the second airplane flew into the picture and and hit hit the building.
Silence. could have heard a pin drop and um we sat there for what seemed like A long time, which was probably just a very few seconds, and uh I I went to the 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?
How did General Caine first learn about the attacks while at Andrews Air Force Base?
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 uh the White House saying, Get anything you can airborne. Um the nation is under attack. And right at that point in time. My boss, Brigadier General Dave Whirley, walked in and I handed him the phone. And I said, make sure that this is this is for you. And we went and and got ready to fly. And uh it was myself and uh a wingman and there were two other folks as well and we got our gear on and and went running back to the ops desk and and uh and met your worly. General Worley read us the rules of engagement for defending the national command authority. It was very liberal and it was on us.
And you know, when you think about leadership for the folks on 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 control. And he reads us verbatim and then he pauses and he looks at us and says, Hey Dan, what I don't know what you're gonna face out there. I think you're probably gonna 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 wanna talk about saying the exact Exact right thing at the exact right moment.
Uh, we ran to the jets and and scrambled and and you know, were 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 ninety three were were assaulting inside the airplane, knowing full well
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Chapters
6 chapters
1
What sparked the conversation about 9/11 with General Dan Caine?
0:00–2:52
2
How did General Caine first learn about the attacks while at Andrews Air Force Base?
2:52–6:21
3
Why did he immediately contact the Secret Service and what was the White House’s response?
6:21–8:43
4
What rules of engagement were given to the pilots and how did they affect decision‑making?
8:43–11:38
5
How did the experience shape General Caine’s view on courage and leadership?
11:38–13:06
6
Why does he emphasize ‘flatness’ and open communication in modern organizations?
13:06–14:55
Speakers
1 identifiedMore from The Daily Stoic
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