General James Harold “Jimmy” Doolittle (1896-1993) was a pioneering pilot, aeronautical engineer, combat leader and military strategist whose career stretched from World War I to the height of the Cold War. He is most famous for leading a daring bombing raid over Tokyo in 1942, the first American attack on the Japanese mainland. Doolittle’s 16 planes dropped their bombs and then, lacking fuel to return to their carrier, flew on to crash-land in China and the Soviet Union.

Jimmy Doolittle: Early Years

James Harold “Jimmy” Doolittle was born in Alameda, California, but spent much of his childhood in western Alaska. His father, Frank, was a gold prospector and carpenter in Nome, where young Jimmy learned to fight bullies and pilot a dogsled. Eventually Rosa and Jimmy Doolittle returned to California, leaving Frank behind.

Did you know? To aid his record-breaking 1922 coast-to-coast flight, U.S. military strategist Jimmy Doolittle invented a funnel-and-tube-based "pilot dehydrator"—possibly the earliest airplane toilet.

Jimmy attended high school in Los Angeles, where he distinguished himself as a gymnast and boxer. He then began courses at the University of California at Berkeley’s School of Mines.

Jimmy Doolittle: First Flights

In 1917 Doolittle became a flying cadet in the U.S. Army Signal Corps. He was soon soloing and serving as a flight gunnery instructor. He later requested a transfer to the European theater, but the armistice dashed his dreams of combat.

Instead, Doolittle worked at the Army’s Kelly Field in San Antonio, Texas, before returning to Berkeley to complete his degree. In 1922 he became the first pilot to fly coast to coast in under 24 hours, making the journey from Florida to California with just one stop. The Army sent him to the Massachusetts Institute of Technology, where he earned master’s and doctoral degrees in aeronautical engineering.

He spent the rest of the decade working as a test pilot for military and civilian planes, setting air race records and helping to develop instruments that allowed pilots to fly in whiteout conditions. In 1930 he left the army for higher-paying work at the Shell Oil Company, where he pressed for the adoption of advanced aviation fuel.

Jimmy Doolittle: The Doolittle Raid

Returning to the army full-time in 1940, Doolittle continued his test pilot work until January of 1942, when he was summoned by General Henry H. “Hap” Arnold to lead a raid on the Japanese mainland. At the time Japan’s defensive perimeter in the Pacific was wide enough to make it invulnerable to conventional carrier-based attacks.

Sixteen Army B-25 bombers were rigged with doubled fuel capacity and loaded on the aircraft carrier USS Hornet. The original plan called for bombing five major cities, but last-minute detection of the Hornet forced the planes to launch a day early.

With Doolittle in the lead, the planes survived storms and anti-aircraft fire to drop four bombs each on Tokyo, striking industrial facilities and a light cruiser. Several bombs hit civilian areas, killing 50 and injuring 400.

The Doolittle Raiders, as the planes’ pilots became known, flew on toward China. They had planned to land in areas controlled by Chinese Nationalists, but all ran out of fuel and crashed. Most of the crews parachuted to the ground, where with local help they were able to reach the Nationalist lines. One crew landed in Vladivostok and was interned by the Soviets. Three died in the crashes, and eight were captured by the Japanese.

Jimmy Doolittle: Aftermath of the Raid

In America the raid was cause for celebration. The 45-year-old Doolittle, who had worried he would be court-martialed for missing his primary targets, was awarded the Congressional Medal of Honor and promoted two ranks to brigadier general.

The attack was a psychological blow for the Japanese, who moved four fighter groups from the war’s front lines to protect their cities. Following the raid, Japanese battalions killed 250,000 Chinese civilians in areas suspected of aiding the American airmen.

Jimmy Doolittle: War Strategy, Final Years

Doolittle was given a series of command roles in North Africa and Europe, eventually leading the powerful Eighth Air Force with its 42,000 combat aircraft. He modified U.S. bomber escort tactics, freeing fighters to pursue their German counterparts.

Doolittle’s last significant mark on U.S. policy came in a classified report on covert operations for Dwight Eisenhower in 1954, which stated that for Cold War espionage, “acceptable norms of human conduct do not apply.”

In 1959 Doolittle retired as a lieutenant general and returned to an executive position at Shell. In 1985 Ronald Reagan promoted Doolittle to a full four-star general. Doolittle died on September 27, 1993, at age 96.