April 2022

Calculated Risk: The Extraordinary Life of Jimmy Doolittle – Aviation Pioneer and World War II Hero

Famous for leading the Doolittle Raid, America’s first strike against Japan in World War II, Jimmy Doolittle led a remarkable life as an American pilot. This firsthand account by his granddaughter, Jonna Doolittle Hoppes, reveals an extraordinary individual:

  • An aviation pioneer who was the first to fly across the United States in less than 24 hours and the first to fly “blind” (using only his plane’s instruments).
  • A barnstormer well known for aerobatics and a popular racing pilot who won every major air race at least once.
  • Recipient of both the Congressional Medal of Honor and Presidential Medal of Freedom.
  • A four-star general and commander of the 8th, 12th, and 15th Air Forces.
  • A scientist with a doctorate in aeronautical engineering from MIT.

Calculated Risk provides insights into the public and private world of Jimmy Doolittle and his family, and sheds light into the drives and motivations of one of America’s most influential and ambitious aviators.

This updated edition contains a new foreword written by Richard P. Hallion, a new afterword written by Clarence E. “Bud” Anderson, and a new introduction by author Jonna Doolittle Hoppes.

About the Author

Jonna Doolittle Hoppes

Jonna Doolittle Hoppes is the granddaughter of Jimmy Doolittle and the author of Just Doing My Job: Stories of Service from World War II (Santa Monica Press). She has taught classes at the United States Air Force base in Los Angeles and has written for such magazines as Smithsonian Air and Space, Air Force Magazine, and Air Power History. Hoppes is president of the Air Force Historical Foundation (founded by General Spaatz in 1953), and an advisor for the Flying Tiger Foundation. She has spoken at the Madingley American Cemetery in England, the ROC Air Force Academy in Taiwan, the Smithsonian Air and Space Museum, the Pritzker Military Library, the Pacific Aviation Museum at Ford Island in Hawaii, the Udvar-Hazy Center in Virginia, as well as at the Air Force Academy in both the United States and England. She has appeared in the television program Man, Moment, Machine, and in the documentary From Vengeance to Forgiveness: Jake DeShazer’s Extraordinary Journey. Hoppes lives in Huntington Beach, California.

Book Club Session

Session Notes:

Air Force Historical Foundation Book Club

Calculated Risk: The Extraordinary Life of Jimmy Doolittle by Jonna Doolittle Hoppes

18 April 2022
80 Groups in Attendance


Opening Remarks by Gen Mike Holmes, (USAF, Ret.): Chairman of the Board, Air Force Historical Foundation

Good evening, and thank you for joining us for the second edition of our book club. If you were here before, welcome back. If this is your first time, we are glad you are here.

Jimmy Doolittle III (Col, Ret.) Opening Remarks: Jonna’s book is outstanding and a wonderful insider’s view of the family. The real hero of Calculated Risk is our grandma, Josephine Doolittle. She was an absolute saint and put up with our grandfather’s high-risk aviation career. Being stalked by reporters, many military moves, two small children, and my grandfather’s endless international travels. He was a patriot, gentleman, scholar, and a warrior. He was the best mix of humility, integrity, humor, and technical brilliance. He was a gregarious and consummate team player, and a member of several aviation-oriented organizations. He was most importantly, a family man. “I could never be so lucky again,” is derived from his belief that he was able to successfully court his wife, Joe. 


Question and Answer Session

  1. Moderator: This book is an obvious labor of love; how important was it for you to capture your grandfather’s fabled story accurately? What process did you follow to you turn his letters to your grandmother into the chapters of his life?

I wrote the book as a direct result of the movie Pearl Harbor. They had him portrayed as a foul-mouthed, not-so-bright, Patton stereotype. Even though they corrected the portrayal, I wanted to put out there with the stories about him and who he really was.

I wanted to write it as a non-fiction narrative as I believe it is the most effective way to convey history. I was particularly lucky because the summer before my grandmother’s stroke, she was able to spend a few weeks with me where I urged her to write them down. That summer, she dictated the stories as I captured them in writing. It is important for people to know how humble and real they were as stories.

  1. Moderator: Was it important for you to capture the role your grandmother played in your grandfather’s life? And what do you see as her greatest attribute as the wife of Jimmy Doolittle?

Jonna: If the Egyptians are right, people come back to earth until their soul is pure light, my grandmother is not coming back. I think her best attribute was to be able to support my grandfather in everything that he did. I think she adored him, as he did her.  

Jimmy: She had a photographic memory, and she would see someone coming and whisper in my grandfather’s ear and who he was and where he was from. It made him look really smart. She may not have been technically smarter than our grandfather but was smarter than him in many ways.

  1. Moderator: I’m impressed by the way your grandfather set out to make himself into the man he wanted, and needed, to be…over and over. Pilot, engineer, businessman, combat leader.  Do you think that is still possible in the world we love in today?

I do think it’s possible, if people take the time to sit back and look at their goals, roll up their sleeves, they can do a lot of things. I think the political and social climate in today’s world can make it difficult, people being willing can do it.

  1. Moderator: How do we balance the idea of calculated risk with all the plane crashes he walked away from? Did his exceptional pilot skills give him additional confidence that he could walk away of thinks went sideways?

Jonna: I think part of it was he had an engineering background. He had a doctorate from MIT. He looked at all the possible outcomes and planned ahead. I think all good pilots do that.

Jimmy: Certainly, he did some wild things in his early days – if you’re trying to record set and do experimental flight tests there are a lot of unknowns. There are several unknown unknowns. You don’t know what dragon you’re about to tickle. They sometimes found things they didn’t know they were going to find. I don’t believe our grandpa ever took off in an airplane and maneuvered willy-nilly.  I think everything he did after his pre-mature days of flying, he did so carefully and methodically. No doubt he was a great stick and rudder man.
Jonna: He spent more time in the aircraft than many other pilots. He worked out options ahead.

  1. Bill Schulke: I am a volunteer at the National Museum of The U.S. Air Force. Is there any mention of the General’s time at Wright Field (now Wright-Patt AFB) that is memorable to you?

Jimmy: I think contact flying is what he was doing – which is what those guys in Alaska do when they know the canyons, riverbeds, and widowmaker trees, but you have to have an excellent memory. McCook Field was the army test field before Wright was built, and it was an interesting place back in the early 20s when aircraft had low wing loading and slow speeds. They had enough people run off, they painted on the roof of one of the buildings that “this field is small, use it all!”

  1. James Gardner: Question for Jonna and Jimmy. Can you share a favorite memory of a time you spent with your grandpa? I’d like to ask the question if possible.

Jonna: I can remember that there was just about anything I could ask my grandpa. I was staying with them one summer and I had a monumental problem. I asked him if I could talk to him. We sat in his office, he was on one side his desk and I sat in the chair on the other side. I started to pour my heart out and then held up his hands and said “hold on just a second” – he then took out both his hearing aids, turned them off, and set them down on the desk and then said “go ahead!” He made me laugh. He could make everyone laugh.  

Jimmy: He grew up in Alaska as an outdoor kid. They used to run impromptu marathons for their own amusement! I was privileged enough to spend a lot of time with him growing up. We hunted doves and quail together often, watching the sunrise. Some of the fellas he started hunting with were fighter aces – we would go to Baja, CA from Edwards AFB. We always had a good night before getting into the duck blind the next morning. Some of the best times were together in a blind with my grandpa. As a teenage boy he offered me one of the few pieces of advice he ever did: “make sure you’re a good citizen in the camp – go clean, haul the trash, etc. – and you’ll always get invited back.”

I got to save his life in Mexico. I heard a buzzing noise from a bush he was about to step across. I yelled at him “Grandpa, what’s that noise?”– and he said “what noise!?” I’m convinced he was completely deaf in that frequency from flying B-25s and other planes. The sound was a diamondback rattler trying to warn him off.


  1. Christina Olds: Question for Jonna and Jimmy. Were each of you aware of your grandfather’s fame? If so, what age did you become fully aware?

Jonna: You always knew he was well-known. People came up to him when we went out to dinner, or the press would show up. You could never get him to talk about himself, but other people. They had a wall of pictures in the hallway –  I would point to the pictures and he would tell me a story. But I did not appreciate the magnitude of his work until I was an adult. If you asked him, he would say the greatest contribution of his career was blind flight.

Jimmy: I knew pretty much from the age of reason that one of my ancestors was a pretty important guy. I don’t really know how to go into that. It turns out I spent my life flying, I did a bunch of RDT&E flight tests.
Christina: Did you get caught up in the anti-war protests and get feedback based on your grandfather’s role in WWII?

Jimmy: I flew about 200 missions out of Thailand – I can remember friends that gave me unending grief about the politics of my participation of what at the time was the noble experiment of the domino theory. One has since apologized in their older years.

Jonna: It was difficult because my dad was in Vietnam. It was a really difficult time.


  1. Bill Strandberg: In retirement your grandmother showed an interest in young Airmen. Did she always show an interest in the young folks working with Jimmy in his various positions? Was she always that kind and caring for them?

Jonna: She’s always had a special place in her heart for people.

Jimmy: She was an absolute wizard in creating enough to eat for people. My grandfather was infamous for bringing home stragglers.

Jonna: And she made beer!!


  1. Did Jimmy ever talk about the Raid? If so, what were his comments?  Did he ever share any fearful or terrifying times with the family? 

Jonna: The ones that standout the most is of Doc White – Doc asked if he could go along on the Raid, but Jimmy said that he couldn’t because of the additional weight. Non-crew members added too much. Instead, Doc White went and trained on the gun so he could go as crew. One time he did talk about himself was when he was dismayed that he could no longer able to write to the families of those who were in the Raid with him.  

Jimmy: He never talked about the Raid, flying combat, or flak. He would speak with a big grin on his face about the ‘good ol days’ at McCook Field of problem solving, technical problems, engineering problems – working with Sperry Gyroscope, Guggenheim Laboratories, and blind flight experiments.

He talked about Roscoe Turner and his lion – and how the lion would climb in his lap during turbulence. He got in the position where he had to answer many philosophical questions about ending the war as quickly as possible with as little loss of life as possible. The losses of the 8AF likely weighed on him terribly.


  1. Moderator: Your grandfather flew some of the greatest fighter aircraft in aviation history: test aircraft, racing aircraft, bombers, and fighters. Which was his favorite to fly?

Jonna: I’m not sure, but the only plane he ever bought was the Super Solution!

Jimmy: Let me discuss the one he was least fond of – Gee Bee R-1. It won him the 1932 Thompson Trophy. It was a horrifically difficult airplane. It had power, speed…but was all afterburner and no rudders. From a stability and control perspective, the Granville Brothers’ planes killed almost everyone that flew them. He was quoted as saying that this was an airplane he needed to fly with kid gloves – he didn’t get in tight on the pylons during the race. After this experience, he left racing because it had ‘outlived its usefulness’ for advancing aviation – too many test pilots had died. If I had to say one, the Spitfire was probably his favorite.


  1. Moderator: Teams are not built accidentally. If you are on a lot of good teams, that is not a coincidence. The book is full of examples of Jimmy being on good teams. Your grandfather was a hands-on leader, which showed in the way he led the training and then the raid on Tokyo, piloting the first plane off the deck. Do you think his greatest strength was this ability to connect with his men? Can you talk about his ability to build teams?

Jimmy: I think it was born in him, in his attitude. I think one of the reasons Russia is struggling is they do not have a strong NCO corps. From the Doolittle Commission – finding that we need grant more responsibility and authority to the Enlisted. This, like his wartime decisions, were innovative and not very popular, especially with those stuck in their old ways.

Jonna: He called it what it was – right was right and wrong was wrong. He lived it. He wasn’t afraid to say so in the face of anyone.


  1. Moderator: Why do you think he was reluctant to accept the Medal of Honor?

Jonna: He felt the Medal should be given to someone who directly risked their life. He felt it cheapened the Medal to be given to someone from the Raid. When they gave him the Medal of Honor, he accepted it on behalf of the Raiders – it belongs to all of them. He never felt he did anything on his own. He always felt it was the team of people that contributed to success – be it racing or the Raid. He truly valued the people on his team.

Jimmy: He wanted to know about the rest of his boys – and why he was the one in the staff car getting the Medal. He had a highly attuned sense of fairness. He gave his superiors an earful over it – but they told him to ‘shut up and color’ and that he was getting the Medal!


  1. Moderator: His decision to allow 8 AF fighters to leave the bombers and kill the Luftwaffe was probably his most momentous decision in the ETO. It paved the way for the Normandy invasion and the destruction of Germany.  How does that lonely decision (that went against conventional thinking) reflect his character?

Jonna: Two nights ago I had dinner with Bud Anderson (triple Ace from WWII). I asked him about this decision. When we released the fighters, they could chase the German fighters anywhere and take them out from the ground or air. The attrition was so high they could not replace their pilots soon enough. Bud would say it wasn’t this decision alone, but a plane known as the P-51 Mustang. I think my grandfather’s fingerprint was still on this though: without the 100 Octane fuel he urged Shell to develop and the military to adopt, it is likely the P-51 engines would not have performed without it.

Jimmy: I just finished a book called The Secret Horsepower Race and it talks about the challenges in developing fighter engines. They didn’t abandon the bombers – the fighters belonged in an offensive role – there is nothing worse you can do than to hobble them to a defensive role. If you want to win, your fighters need to be on the offense. With a survivable ratio of combatants, the found everything they could and shot the hell out of it. Near the end, Germans were putting pilots into combat with 25 hours of flight. Changing the mission of fighters to offense was one of the most pivotal things he did during the war.
Jonna: According to the German Ace Adolph Galland, that decision ended the Luftwaffe.


  1. Moderator: What words of wisdom do you think your grandfather would have for Airmen serving now, in 2022? 

Jonna: His philosophy on life was to leave things better than you found it. He believed in the Golden Rule and being the best person you can be. He used to say “Country, job, family” – without his country, he could not have his job; without his job, he could not support his family. I think that was his whole mission. Everyone has something that they can give, something they can contribute. He would say do it, and to the best of your ability. 

Jimmy: There was a wonderful TED briefing talking about the 1%. There is currently 0.5-1% of the nation that has been in the service. It is a very different nation right now and is less unified. It is a difficult time with a lot of polarity. Go back to the Golden Rule and trying to do the right things.

Closing Remarks
Jonna: Thank you everyone for coming – and for supporting the Air Force Historical Foundation. Especially Jimmy – I know you don’t speak in public often. You have wonderful stories and thank you for sharing them. 

Jimmy: I want to address the question about the Space Force. In 1961, I have a vivid memory of sitting on a sandhill not very far from the space launch facility at Vandenburg with my grandfather. The mission was Discovery 23, which they told me at the time was a scientific research satellite, not a reconnaissance satellite. Space Technology Laboratories spun off another – both were kingpins of the DoD attempts to get into the Space Race. He was up to his Adam’s apple in the space stuff in 1959-1960!
Gen Holmes: Thank you both for taking the time to join us, thank you everyone for coming out. Come join the Historical Foundation and see you next time!