198: Soaring to Glory: A Tuskegee Airman's Firsthand Account of World War II with Harry Stewart
7 Dec 2025 · 22 min
Episode 198 of the Heroic Investing Show features an interview with Harry Stewart (Tuskegee Airman). Stewart recounts his upbringing in Queens, enlistment and training at Tuskegee Army Airfield, earning his pilot wings and commission in 1943, and flying primarily P-47 and P-51 fighters as part of the 332nd Fighter Group (Red Tails). He flew 43 missions—primarily bomber-escort missions across Central Europe (Germany, Austria, Italy)—including a notable April 1, 1945 fighter sweep over Linz, Austria where comrades were shot down and one (Walter Manning) was lynched by a mob. Post-war, Stewart earned a mechanical engineering degree from NYU, worked in engineering (pipeline company), served in the Air Force Reserve (retired at 60), later participated in veteran chapters, authored/was subject of a biography titled "Soaring to Glory: A Tuskegee Airman's First Hand Account of World War II," and remains active in aviation into advanced age (states he will be 95 on July 4).
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We help current and prior first responders put protections, systems and a team in place to help them build a life where they can focus on their passion, that service or product that they are uniquely gifted to share with others, making the world a better place for all of us. My name is Gary Pinkerton and I co host this show with Jason Hartman. This is episode 198. My guest today is a World War II veteran. That's right, my second World War II veteran to come on Heroic Investment Show. It is just incredible to have experienced the energy, the fire, the vitality, the optimism that I saw in Harry Stewart. Harry was a member of the Tuskegee Airmen, the famous African American pilots that manned the Red Tail Squadron in Europe in World War II. While still a teenager growing up in New York city, Harry Stewart Jr. Enlisted in the war effort and joined the legendary ranks of the Tuskegee Airmen. He earned his Wings end Commission in 1943. But his youth did not hinder his ability to become one of the most famous of the Tuskegee Airman pilots of World War II and beyond. I am just blessed to have gone through this conversation and done this interview with Harry. He's an amazing guy. His stories are quite impressive and we actually videoed this interview and hopefully I'll get it up on YouTube or get it up maybe on Facebook here in the near future. He's just a great guy to listen to and I think he's extremely inspiring. We're not going to get an opportunity to talk to too many more World War II veterans, certainly that had the courage to face an incredibly uphill battle, which was being an African American pilot in World War II. And he also talks about the challenges from just manning a squadron where the requirements were that you were African American and that they didn't have the backfill that everybody else did so flew back to back to back missions. And they stayed over there in Europe a lot longer than normally we were putting pilots through. So incredible American heroes. I was blown away. So I hope you enjoy this episode with Harry Stewart.
The audience just loves to hear stories and lessons you've learned about life. Tell your story if you're okay with that.
The story. Just let me say that the book is both inspirational and that's the story of my life during the World War II and the experiences I had and historical how the Tuskegee Airmen, that was the African American pilots got to be and the trials that they had to go through in order to establish themselves. As far as I'm concerned. I was born in Newport News, Virginia, but my folks moved to New York City when I was about 2 years old in the borough of Queens and near an airport called North Beach Airport, which is now LaGuardia Airport. And I guess that's where my interest in aviation started. And I used to see the old 1930 vintage aircraft flying around. And I said, I want to do that. I want to be a pilot, you know, and I wanted to fly and that type of thing. So I guess any aviation magazines, any of the aviation clubs or anything like that that were prevalent at the time I joined became part of. And as fate would have it, World War II was about to start. But I learned a horror story there that the Air Corps did not accept African Americans for training as pilot training. And their claim was that they did not have a segregated base that they could train the pilots on. But with the activity of the various newspapers, the politicians, all this sort of thing, the Air Corps relented and they said, yes, we will go ahead and train African American boys as pilots, but it would have to be on a segregated basis. So that's how Tuskegee Army Airfield was built in Tuskegee, Alabama. And that was just about 10 miles away from the Booker T. Washington College that was down there, Tuskegee Institute or Tuskegee College there. So I think it was a good choice as far as the location was concerned. I had heard about this and read about the forming of an all black fighter squadron called the 99th Pursuit Sergeant. And I immediately, at 17 years old, went down to the registration recruiting office and said, I want to join the 99th Pursuit Squadron. Well, those guys never heard of the 99th. They said, well, you'll just be sent wherever we send you. That's where you go. But anyway, they let me take the examination for the Cadet Corps and I passed it and being 17 at the time there, I couldn't go in until after 18. So it so happens that I went into the service at 18, about the same day that I would have been drafted or conscripted into the Army. I was sent down to Kiestler Field, Mississippi, just for six months indoctrination. And then I was sent up to the base where I was going to be finally housed at, and that was Tuskegee Army Airfield. So I went through the regular curriculum that they had there. Or let me say first, I went through six months of college training at Tuskegee Institute on the campus. So I lived on the campus for six months. Then I was sent over to the air base, which was about 10 miles away, and started the 10 months of pilot training, at the end of which time I got my wings and I got my second lieutenant's bars. I was all of 19 years old and didn't even know how to drive a car yet. And being from New York, you didn't need a car. They had the rapid transit system and that type of thing. So that wasn't unique for a New Yorker, but it could be unique for somebody in other parts of the country. And then after some further training in fighter aircraft, the P40 Warhawk, which was like the Flying Tigers with that tiger face on it, and the P47 called the thunderbolt, that was sent overseas to join the 332nd Fighter Group, called the Red Tails. Called the Red Tails because that's what they. The red painted tails there.
Beautiful airplane.
Yes, that's right, the P51 Mustang, and flew 43 missions over there and came back home, flew the P47, and was involved with a number of events that took place between then and 1950. And then I got discharged in 1950. I decided to go back and get my college education. So I went to New York University, got a degree in mechanical engineering, and at that time I decided move up the corporate route as far as my vocation was concerned, and then retired about 19, in late 1980. And after I retired, I decided to take up some phases of flying again. During the time I was going to school and working, I wasn't doing any flying, but I got an additional notation on my license as a commercial pilot in gliders. I just used that to go ahead and take up some local kids and take them up on the weekends and show them what it was like to fly, hoping that it might inspire them to go ahead and seek vocation in the aeronautics field. And I was flying. Let's see, I got my license at 81. I was flying from 81 until I was about 88. And then I decided, well, the solo flying was doing was enough there, so I still fly a little bit. And it was just, I guess, last year I was up in a dual seater P51. It was a modified, but they had two tandem seats in there and they had a dual set of controls. So I had chance to go up and do a few slow rolls and loops and all of that sort of thing. So I'm having a lot of fun in my old age. I'll be 95 on July 4th, so I'm getting there.
Well, the audience can't see this, but I would have pegged you at about 80, not 95, maybe even 80. I've seen people younger than 80 that look definitely worse than you do. My gosh, what an incredible history. I've the true pleasure now of interviewing now three World War II veterans and a Korean War veteran on this show. And it is just humbling to hear your stories, hear that you retired from two full careers in 1980 and all the amazing stuff that you've done since then. You left the military in 1950 as a lieutenant colonel.
No, I left as a captain. And I stayed in the reserve.
Reserves.
Okay.
And worked my way up in the reserve. Took two weeks training at one of the airfields per year and did some other things to earn points towards retirement and retired at age 60.
Nice. And are you still in the New York area?
No, no, I'm here in Bloomfield Hills, Michigan.
Michigan?
Yeah. My last job. My last job brought me to Michigan. I was with a international pipeline company engineer with them. And when retirement came along, I kind of liked Michigan here. And I said, I think that the pace that the New Yorkers keep is a little too much for me. I like more of a sedentary life. So here I am. I decided to retire here In Michigan, about 20 miles north of Detroit.
Wow. Well, thanks for that. My sister lives in Detroit and there's been some challenges in the world, the industry there in Detroit.
I sure have.
One of the things that. I mean, gosh, you said 43 missions.
Yes.
How was that compared to people who were around you in your squadron? Was that a lot? Was it a few. You know, I know that attrition was pretty rough there.
Yeah. In the 15th Air Force, the fighter groups there, the 50 missions was a standard. Then they looked at it from an actuarial standpoint. You know, how far can you feel as though the life expectancy would go, Number of missions you take for instance, the bombers were a lot more vulnerable. So theirs was 35 missions and they go home. So with the fighters, it was 50 missions. But because of the problems that we had with the desegregation and the only replacements that we would get would be from Tuskegee itself is that our commander asked us if we would stay on for 70 missions, which we took as his wish was our command. So that was it. So some of the guys actually got 70 missions in. But the war ended when I had my 43rd mission.
Got it.
So you did a lot of missions in Germany. I'm guessing they're probably a large focus.
All up in Central Europe there, Germany, Austria, and, you know, all around that area. A few in France, but mostly in Germany and Austria.
Your purpose was escorting, protecting the bombers?
Absolutely. That was our primary job, was bomber escort and to ward off enemy fighters that might come in to try to knock down the bombers down. That was the primary mission. Wow.
Gosh. So you were in there in the thick of it, and your survival actuarial tables were better, only really because you weren't flying a big old heavy pig, I guess it was harder to hit.
That's right.
Wow.
Any specific mission or event that you like to talk about or do you think would be most interesting?
Well, I guess the one that sometimes I'm often asked to talk about is the. I forget whether which it was. It was a 30some mission that I went on, but it was a bomber escort to Wells, Austria. That was near the end of the war there. And the fighter groups at that time were given permission if the bombers, they felt as though. Or the bombers felt as though they were in a safe zone and they could get home okay without the fighters there, that the fighters could stay, hang around and do what's known as hunt for targets of opportunity. Targets of opportunity being any type of interdiction as far as barge traffic is concerned, on the rivers or railroads or moving vehicles on the ground, and of course, enemy aircraft. Also. The mission that I was on that I'm thinking about was April 1, 1945, and we were released by the bombers. The bombers said, we're okay. You can go on your own now. So we decided to go on targets of opportunity and what we call a fighter sweep. And we ran into a. A horde of German fighters. They were focke wulf, 190s. And fighting ensued there. And three of our guys got shot down. One not so bad that he couldn't make it back to friendly territory in Yugoslavia. Another was killed outright when he was shot down. And then there was a third by the name of Walter Manning who bailed out. And this was over Linz, Austria. When he bailed out, he was picked up by a local mob and they took him to the local jailhouse where he was jailed. And the SS troops, the German troops came in and they were whipping up the crowd with the anti sentiments against the American birdmen. And they whipped the crowd up into a frenzy enough where three nights later the crowd broke into the jail and, and took Walter out and they beat him up pretty badly. But the worst thing is that they hung him from a lamppost. They lynched him. Oh, boy. Wow. Right? This was not that unique. I mean, it happened to a lot of our guys. And you can understand the byline was with the bombers and with the fighters. You know, if we just bomb this town, you know, and it looks like you're going to go down, get out of there and get as far away as possible that you can from the town because of the understandable sentiments, of course, at the time. The interesting thing about that mission I talk about is that a year ago on April 1, I was invited over to Austria by the Austrian government and.
They were contrite about their citizens having lynched one of the airmen, Walter Manning there. And they decided to pay a tribute to him. And not only that, but he wrecked a memorial, memorial to them. And they wanted to find someone who had been on that mission with them. And I was on that mission with them. So they invited me over and I had chance to see the ceremony, which was absolutely beautiful. And I have to commend the Austrians for what they did because I thought it was a brave mood, a brave move as far as, you know, morality of the whole thing was concerned. And they showed their contrition by doing this. So a very nice thing.
I'm sure that was a very touching, very moving experience.
Yes.
Had you been to Europe's between the war and then or Eastern Europe?
Yes, not eastern Europe, mostly western, you know, France and Italy and of course that's where I was stationed actually, in Italy and in southern Italy. And we flew on our missions from Italy up into Germany and that area there. The missions were pretty long. They were, oh, maybe anywhere up to six and a half hours. We did make one mission to Berlin, which was 1600 miles round trip escorting the bombers. And that was. Took us about six and a half hours. And we're going at the ground speed about the bombers there, which they're going along at ground speed or an airspeed and Ground speed of maybe 200 miles an hour, and we're flying along at maybe 250 or 270 miles an hour. So actually we have to crisscross back and forth so that our ground speed matches the ground speed of the bombers. The missions, they were cold because we were up at 35,000ft around that way.
Escorting the bombers and out of shelling range, I guess.
Right? Yes. In shelling range. Well, the bombers were really getting the big part of it. You know, the aircraft guns were tracking them at the altitude that they were at. We might be 1500ft above them. But every once in a while, one of those shells would get up around us also, you know, and it's kind of scary.
Of course.
Of course.
How many of your old squadron mates are around? Are you kind of the senior guy or.
Well, I'm not the senior, but I'm one of the 12 that's left. And when I say 12 that's left, that's. Of the combat pilots who were In World War II of the Tuskegee Airmen, there are 12 living today. Well, out of 351 that eventually that went overseas at other periods.
Well, I'll tell you, if you've picked 351 people of normal society from that era, it would probably be less than 12 of them around. You guys are tough old guys.
Obviously, everyone really appreciates the incredible efforts that you did. Do you all get together frequently?
Yes, they have the annual get together that they pick in different parts of the country. This year. I think it's going to be in Las Vegas. And then you see the shirt I have on. This is the Detroit chapter and they have chapters in almost every state. And that's when they get together for the annual convention. So this is the chapter stuff that I wear when I go to one of the chapter meetings. And that's it. Wow.
So we didn't mention really how to get in touch. There is a lot out there about the Tuskegee Airmen. But before we started recording, we were talking about the book that's really to firsthand account viewer. It's a biography for you, almost autobiography, but somebody else, an author, penned it.
It's a biography. That's right. Yeah.
Yeah.
And it's called Soaring to Glory A Tuskegee Airman's First Hand Account of World War II. And we've given some of those accounts. But I can't wait to dig into this book. I love the story of the Tuskegee Airmen. The bravery there. Not just against. Against the bullets you were going after, but the kind of the American sentiment at the time, it's pretty hard to believe for listeners in today's audience that you had to train on a segregated base. And we know the history is there, but just imagining that that was actually normal is pretty hard to imagine. But thank you for your service, sir. And I know that there's websites for Tuskegee Airmen. The book is definitely awesome. Any other thing that you think that the listeners should go check out if they're interested in the history?
Well, as you were saying and alluded to is that I think the book gives a lot of the vignettes that they might be very interested in. You know, they're light hearted parts. And then there are parts that goes into quite a bit of depth. But also the author, I'd like to say that Philip Hannelman did a very good job as far as tracing the history of how the Tuskegee Airmen developed in the first place and some of the trials and tribulations that they had to go through in order to get established. So it's a beautiful book from the standpoint of both those.
Items. Wonderful.
Well, the Tuskegee Airmen continue to inspire young individuals out there to be bold and to go against kind of set ways. I love the organization. I love the history of it. It's very easy to find out information about them. And again, I just love members that I have met. Very blessed to have you on our show. Lieutenant Colonel Harry Stewart, thank you so much for joining us and giving us a few minutes of your time.
It's been a pleasure.
I hope you have a wonderful summer out there in Michigan.
Thank you. And you do the same.
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