The first few months of 1942 were grim ones for the United States of America. Following the attack on Pearl Harbor, the country found itself involved in a war that it was completely unprepared for, as shown by the string of humiliating defeats inflicted on it by the Japanese military following its success in Hawaii. Meanwhile, in Europe, the Nazis were in the ascendency all over the continent, and were sending U-boats to sink ships within sight of the American coastline. Casualties mounted while morale plummeted.
President Franklin Roosevelt knew that, given enough time, the mighty American industrial machine could be transformed into “the Arsenal of Democracy” that could outpace the Axis powers in terms of military might, and that the American people had the will to fight, but they needed to be shown that their enemy, particularly the Japanese, could be beaten. In other words, they needed a morale booster.
To get it, Roosevelt turned to a man that was already famous across the country for his daring feats behind the controls of an airplane. Jimmy Doolittle had spent the last two decades making a name for himself in the air, accomplishing things no pilot ever had before and advancing the science of aviation to make it safer and more efficient for pilots and passengers in the process. But now what he was being asked to do appeared to be a suicide mission: to lead a raid of Army bombers deep behind enemy lines, to strike at Japan itself.
To pull it off would not only require courage, but also precise planning, extensive training, and a good bit of luck too. Luckily, Jimmy Doolittle possessed all of these things, particularly luck: by 1942 he had survived so many air crashes that many people began to believe that the only reason he was still alive was because God was protecting him. Now he would call on that uncanny luck (or divine protection) once again in order to drive a needle straight through the heart of the Japanese Empire, and in the process, become one of the most famous men in America.
The Little Kid with Big Dreams
James Doolittle hadn’t had an easy time of things as a child. Born in 1896 in California, when he was 4 his family moved to the remote frontier town of Nome, on the northwestern coast of Alaska, part of a wave of some 25,000 who flooded the area following the discovery of gold in the area. Five years later, almost all of them were gone, unable to stand one of the toughest environments on Earth: situated only 100 miles south of the Arctic Circle, the average daily temperature in Nome only rises above freezing for 5 months out of the year. During the long winter months, the harbor completely ices over, making dog sled teams the only means of transportation.
One of the few families who stayed in Nome was the Doolittles. Young Jimmy knew he needed to be tough in order to survive, and developed a reputation as a brawler: would-be bullies discovered the little Doolittle boy packed quite a punch. He stayed in Alaska until 1908, when he moved back to the “Lower 48” with his mother, Rosa. His father Frank stayed behind, and for the rest of his life Jimmy would have a distant relationship with him, only seeing him on a handful of occasions.
In his new home in Los Angeles, Doolittle continued to get into schoolyard fights, until a boxing coach pulled him aside and offered to teach him how to fight “properly.” He was a talented amateur pugilist, winning the West Coast Amateur Championship when he was just 15 years old. History might have looked very different had he continued on in the sport, but instead, Jimmy fell in love with his classmate, Josephine Daniels, known to everyone as “Joe.” Joe was a very bright girl, and her family offered to pay for her to attend law school, which was practically unheard of for a woman in those days. Still, the condition for her attendance was to stop seeing Jimmy Doolittle, who her family believed would never amount to anything. Jimmy and Joe struck a fateful bargain: he would give up boxing, and she would give up law school. The high school sweethearts would enjoy a 70-year-long marriage together.
Jimmy attended UC Berkeley, studying at the College of Mines, but his real interest was in the fledgling aviation field. He had seen his first airplane in 1910, when he attended one of the first air shows in the United States at Dominguez Field. He became enamored with flying, and when the United States entered World War I in 1917, he jumped at the chance to become a pilot himself, joining the Army as a flying cadet.
Scientific Daredevil
Jimmy Doolittle soon proved to be a skilled pilot, skilled enough that he was appointed a flight instructor, training other Army pilots to fly. The assignment prevented him from being sent to Europe to fly in combat missions, much to his disappointment. When the war ended, most of the troops were mustered out of service, but Doolittle chose to remain in the Army Air Corps, knowing that it likely represented his only opportunity to keep flying.
During the 1920s, as American military spending was slashed, Air Corps leadership sought to keep aviation in the headlines by encouraging their pilots to perform various feats to draw the public’s attention. Jimmy Doolittle enthusiastically participated in a number of these events, and by the end of the decade, he was recognized not only as one of the Army’s best pilots, but also as one of the most famous men in America. His exploits were legendary: he became the first pilot to fly coast to coast across America in under 24 hours in 1922, won air races in all sorts of aircraft, beating out the best Europe and the US Navy had to offer, and successfully demonstrated the effectiveness of his airplane to the Chilean military on a sales tour in 1926 despite flying with two shattered ankles from a fall.
You might be forgiven for thinking that Doolittle, like so many of his contemporaries, was simply a reckless daredevil: a cowboy of the sky with a devil-may-care attitude towards the risks inherent to his profession. But that wasn’t so: Doolittle was highly intelligent, earning both Master’s and doctoral degrees in aeronautical engineering from the Massachusetts Institute of Technology (MIT), one of the few pilots of his era that also had detailed engineering knowledge. He sought to understand the aerodynamic forces at work on his airplane while it was in the sky, not only to get the most out of his machine but also to make sure he got back to the ground safely. Before attempting one of his famous “stunts,” like when he became the first pilot to successfully complete an “outside loop” maneuver in 1927, he not only practiced for weeks ahead of time but also went over his plane with a fine-toothed comb, making sure everything was in perfect working order.
Doolittle used his unique skillset to advance aviation knowledge and safety for the entire industry, both military and civilian. His most important contribution came in 1929, when he successfully performed the world’s first “blind” flight: taking off, flying around, and landing without being able to see outside the cockpit, relying only on the flight instruments he’d been working with engineers and scientists to develop. These instruments, which allow pilots to safely fly even at night or in poor weather conditions, made commercial aviation safe and reliable enough to be feasible, and passenger numbers steadily increased every year afterward from then on.
A Daring Plan
Doolittle left active Army service in 1930, taking a more lucrative job with the Shell Oil Company as manager of their Aviation Department. In this role, he gradually transitioned from being a daredevil and pioneer to being more of an advisor, one of the country’s most respected aviation minds. He wasn’t a young man anymore, he had a wife and two young sons at home to think about. He was also a firm believer in knowing your limits: he’d been lucky enough to walk away from more than 10 plane crashes without a scratch so far but figured his luck wouldn’t hold forever.
Doolittle watched with growing alarm the deteriorating political situation in the 1930s, fearing that war with Nazi Germany and Imperial Japan was inevitable and that both their air forces were far superior to America’s. He urged the Air Corps, renamed the Army Air Force in 1941, to spend more money on developing new planes, and to produce them in greater numbers. To that end, he was mustered back into military service as an advisor to Air Force chief General Henry Arnold in 1940, making recommendations on how automobile manufacturers could successfully retool their assembly lines to make aircraft in case of war.
In December 1941, war did come to America, as Japan crippled the Pacific Fleet at Pearl Harbor and then busied itself conquering as many American and Allied possessions in the Pacific as they could: Guam, Wake Island, the Philippines, Singapore, the Dutch East Indies, Burma, Malaya, and more. Defeat followed defeat on all fronts, causing American morale to plummet. President Roosevelt knew that his country needed time to fully mobilize for war, to build up the armed forces, and to take the fight to the Axis powers. In the meantime, what he needed was a morale booster, some small success to show that the Japanese, in particular, were not invincible, that they could be beaten.
The plan his advisors came up with was a retaliatory bombing raid on the Japanese home islands, particularly the capital, Tokyo. The destruction caused by the bombing itself was secondary to the effect it was hoped it would have, both on the Japanese public as well as the Americans. The problem was that the Allies did not have any airfields within striking distance of Japan. Instead, they would have to rely on one of the Navy’s aircraft carriers, and since none of the Navy’s planes had the required range, they would have to use Army bombers. This had never been done before; many people thought that it couldn’t be done. But if there was anyone in the US military who could attempt the impossible, it was Lieutenant Colonel James Doolittle, which is why General Arnold made him the commander of the operation.
The Doolittle Raid
The 16 aircrews selected by Doolittle to participate in the raid all volunteered for the mission without knowing anything about it except that it would be dangerous. Secrecy was essential: if the Japanese were forewarned about it, their defenses would be ready, and the mission would be a disaster. The plan was for the raiders to take off from the carrier USS Hornet as close to Japan as it could get without being spotted. The 16 B-25 Mitchell bombers would fly over Japan, bomb their assigned targets, and then continue west to China, where they would (hopefully) land at friendly airfields and rendezvous with Chinese forces fighting the Japanese.
The biggest immediate challenge was how to get the bombers, which were designed to take off from a land runway a mile long, to successfully do so on the pitching deck of an aircraft carrier less than a tenth of that distance. In order to accomplish it, many modifications to the B-25 needed to be made, including the replacement of some of the defensive machine guns with broomsticks painted black. The pilots, meanwhile, needed to learn how to lift the planes off the deck at a much slower speed than they were used to, going against everything they had been trained to do before.
On April 2, 1942, anyone traveling across the Golden Gate Bridge in San Francisco was privy to a strange sight: the Hornet sailing into the Pacific with 16 green-painted Army bombers strapped to her deck. Sixteen days later, the Hornet, along with its escort ships, were 650 nautical miles east of Japan when they were spotted by a Japanese patrol boat. USS Nashville quickly sank the enemy vessel, but the commander of the task force, Admiral Halsey, worried that the boat might have radioed a warning to the mainland: their cover was blown.
The task force was still 10 hours and 200 miles away from the raid’s intended launching point, making it highly unlikely that the bombers would have enough fuel to safely land in China. It seemed like the raid would be a suicide mission. Colonel Doolittle told his men that they could back out now if they wanted, no questions asked, but nobody took him up on it. The 45-year-old Doolittle strapped himself into the lead plane on the deck: he would take off first. He had told his men beforehand that he had no intention of being taken prisoner by the Japanese: if his plane was shot down over Japan, he intended to deliberately crash it into whatever military target he could find.
War Hero
All 16 bombers successfully took off from the Hornet and headed for Japan. Despite getting advance notice that they were coming, the Japanese were still caught by surprise when the bombers appeared over some of the country’s largest cities: Tokyo, Yokohama, Nagoya, Kobe, Osaka, and Yokosuka. They bombed military and industrial targets and then “bugged out,” with no planes being shot down. The planes now headed for China, except for one that instead landed in the Soviet Union, where the crew was interned because the USSR was not at war with Japan in 1942.
There seemed to be little chance of the remaining raiders even making it to the Chinese coastline, much less successfully landing, but then the same luck (or divine intervention) that had followed Doolittle his entire career came through again: a friendly tailwind buoyed the planes, giving them an extra 25 miles per hour of speed, just enough to get to Eastern China. All 15 planes then either crash-landed or their crews parachuted out: Doolittle himself landed in a dung-filled rice paddy near the city of Quzhou.
Surveying the wreckage of his plane, Doolittle believed the mission had been a failure. None of the planes had made it to their destination, many of his men were still missing, and the damage done to Japanese infrastructure had been minimal. He expected to be court-martialed when he returned to the US. He was thus caught totally off guard when he returned to find himself one of the country’s earliest war heroes. He was promoted two ranks, to Brigadier General, and the President gave him the country’s highest decoration for valor, the Medal of Honor. The Tokyo Raid, also called the “Doolittle Raid,” had the exact effect on morale that Roosevelt had been hoping for: American spirits were bolstered, feeling that the country was finally striking back at the Japanese after five months of being on the defensive.
Meanwhile, in Japan, the raid was a humiliation for the military high command. Government propaganda had been telling the Japanese public for years that their islands were divinely protected from foreign attack, so to have American ships and planes sneak right up to the Emperor’s doorstep represented a huge loss of face. Japanese soldiers took out their anger on the Chinese civilians in the area where the Raiders had landed, brutalizing and murdering tens of thousands of men, women, and children in a campaign of terror that lasted for months.
Today, the raid is considered by historians to represent a significant turning point in the Pacific Theater of World War II. Not only were the Japanese compelled to pull forces back to defend the home islands, but the raid convinced Admiral Yamamoto that the American aircraft carriers represented a serious threat to continued Japanese naval dominance in the Pacific, and set out to destroy them. This culminated in the decisive battle of Midway in June, in which four out of the six Japanese carriers whose planes had attacked Pearl Harbor were sunk by the US Navy.
The Old, Bold Pilot
Jimmy Doolittle would spend most of the rest of the war in the European Theater, steadily rising in rank and responsibility as he went along. This culminated in his being named commander of the “Mighty Eighth” Air Force in 1944, charged with overseeing the strategic bombing campaign against Germany. Doolittle is best known for changing a long standing policy requiring escort fighters to remain with the bombers at all times, instead instructing them to fan out ahead of the “heavies” to target Luftwaffe planes before they had a chance to attack them. The fact that the Luftwaffe was almost totally absent from the D-Day campaign and for the rest of the war thereafter is a testament to the success of the change in strategy.
Doolittle ended the war as a three-star general, and left active service in January 1946 (though he remained in the reserves until 1959). He continued to consult with the US government on several projects throughout the 1950s and ‘60s, including serving as the director of the NACA, the agency that preceded NASA. He had a very active retirement, traveling extensively, including an annual trip to a reunion of the surviving Tokyo Raiders. The highlight of the reunion was a solemn ceremony where those in attendance toasted those who had passed on using engraved silver goblets filled with cognac. When one of the Raiders passed on, his goblet was turned upside down. This reunion was held until 2013 with the last survivor of the group, Richard Cole, passing away in 2019.
Jimmy Doolittle was showered in awards and decorations both in the United States and in other countries, including being named Knight Commander of the Order of the Bath by King George VI and receiving the Presidential Medal of Freedom from President George HW Bush in 1989. He’s also been portrayed on several occasions on the silver screen, most notably by Spencer Tracy in 1944’s Thirty Seconds Over Tokyo, as well as more recently by Alec Baldwin in 2001’s Pearl Harbor and by Aaron Eckhart in 2019’s Midway.
The real-life Jimmy Doolittle passed away in 1993 at the ripe old age of 96. He was buried alongside his wife in America’s most hallowed ground, Arlington National Cemetery, with full military honors. The service was attended by both the Secretary of Defense and the Chief of Staff of the Air Force and included a military flyover of both contemporary as well as World War II-era planes.
Doolittle entitled his autobiography I Could Never Be So Lucky Again, and in many ways, good fortune was key to his success both in the air and on the ground. He happened to come of age right at the dawn of aviation, war broke out when he was a young man, allowing him to learn to fly, and of course he was lucky in that he survived so many close calls and outright crashes that could easily have killed him.
But luck can only take a man so far: Jimmy Doolittle was also one of the best pilots of his era, and with his detailed knowledge of engineering and aerodynamics, what seemed impossible to others seemed perfectly obtainable to him. Few other men in America were both smart enough, and “crazy” enough to attempt something like the Tokyo Raid in the first place, but to Jimmy Doolittle, the raid was never “crazy.” It was risky, sure, but like most of the other decisions he made about flying, it was a risk he took after carefully weighing the odds and deciding it was worth the attempt. Put more simply, Jimmy Doolittle was the master of the calculated risk, and that’s why he not only survived his long career in the air, it’s why he’s gone down in history as one of the world’s greatest aviators.
