Dick Cole had always dreamed of soaring into the clouds, but he never dreamed that one day he would fly into the history books alongside his boyhood idol.

As a youngster growing up outside Dayton, Ohio—hometown of the Wright Brothers—Cole pasted newspaper articles chronicling the exploits of pioneering aviators into his scrapbook and often made the 30-minute bike ride to McCook Field where he sat and watched daredevil pilots such as James H. “Jimmy” Doolittle, who in 1922 made the first cross-country flight in under 24 hours, train and test new aircraft at McCook Field.

Lt. Col. Richard Cole at Arlington National Cemetery, May 23, 2014. (Credit: Melina Mara/The Washington Post via Getty Images)

After graduating from high school, Cole took to the skies himself and was a member of the U.S. Army Air Forces when the Japanese attacked Pearl Harbor. Four months later, the 25-year-old was among the 80 airmen selected for the dangerous raid led by Doolittle to bomb the Japanese mainland. The fly boys had been trained to take off from airfields, but the B-25 bombers would have to take off from the deck of USS Hornet in what was the first-ever joint mission between the Army and Navy.

On the morning of April 18, 1942, the Navy flotilla encountered and sank an enemy patrol, which forced Doolittle to launch the raid hours earlier and from a greater distance than planned. Cole was awoken from his sleep with news that the mission was beginning immediately. Although the B-25s had never launched from an aircraft carrier in combat and the airmen didn’t know if they would have enough fuel to complete their mission, Cole did not panic with the hasty change in plans.

B-25 bombers on the deck of USS Hornet before the Doolittle Raid.

“I had my own confidence, but we all had Jimmy Doolittle,” Cole told the San Antonio Express-News. His confidence flowed into us and we would have followed him anywhere.”

With Cole serving as Doolittle’s co-pilot, Crew Number 1 made the unnaturally short takeoff and was the first of the 16 bombers in the air. To avoid detection, the Doolittle Raiders flew in single file for hundreds of miles just 200 feet above the water. Crew Number 1 bombed industrial and military targets in Tokyo, while other planes hit Yokohama, Kobe, Osaka and Nagoya. The resulting material damage was limited, but the psychological damage left behind by the Doolittle Raid was enormous. Shaken by the ability of the Americans to attack their mainland, the Japanese military responded with the Battle of Midway, which became a pivotal American victory in World War II.

Jimmy Doolittle and his crew in China after the raid.

After dropping their bombs, the Doolittle Raiders continued on to China where they hoped to land at airfields controlled by Nationalists fighting the Japanese. A violent thunderstorm and fuel gauges running close to empty, however, testified that the intended plan was not possible. “Our only course of action was to climb up to what we thought was a safe altitude and fly until we ran out of fuel and bailed out,” Cole said in an oral history interview posted on the National WWII Museum web site.

All but one of the 16 planes in the Doolittle Raid crashed-landed on or near the Chinese coast. (The other crew landed in the Soviet Union.)

As the storm raged, Cole jumped from the plane into a 9,000-foot abyss of darkness, broken by only the occasional lightning flash. Not knowing what danger lurked in the mountains below, the airman pulled the ripcord so hard that he gave himself a black eye. “My parachute drifted over a pine tree and left me hanging about 12 feet off the ground. I didn’t know that until the fog cleared away and the rain stopped the next morning,” Cole told the San Antonio Express-News. “And being a young kid that was pretty good at climbing trees, it was very easy for me to climb down and readjust my parachute into a backpack and start walking away.” While the Japanese captured two of the American crews, Cole successfully reunited with Doolittle at a nearby camp and was eventually rescued by an American aircraft.

Lt. Col. Richard Cole visits the grave site of Lt. Col. Jimmy Doolittle at Arlington National Cemetery on May 23, 2014. (Credit: Melina Mara/The Washington Post via Getty Images)

Sixty-one of Doolittle’s men survived the raid and World War II, and in December 1946 they reunited in Miami to celebrate the 50th birthday of their leader. “Early on Doolittle promised the survivors he would throw a party for them,” Cole told the National World War II Museum. “It gave us a chance to renew the camaraderie of the group, and it gave us a chance to honor the people that gave their lives on the mission and those who had left the group since.”

The men had such a good time that the reunion became an annual affair. In 1959 a new tradition began after the city of Tucson, Arizona, presented the Doolittle Raiders with 80 silver goblets, one for each participant. Each man’s name was etched twice on his goblet—one right side up, the other upside down. At each reunion, the raiders raised their goblets and toasted each other with a sip of 1896 Hennessy VS cognac, its vintage matching Doolittle’s birth year, before turning upside down the goblets of any men who had died since their last meeting.

The Doolittle Raider goblets on display in the Air Power Gallery at the National Museum of the U.S. Air Force. (Credit: U.S. Air Force photo)

Cole built a portable, velvet-lined display case that was used to transport the goblets each year to the reunion locations, which moved around the country. Since 2005, the goblets have been kept on permanent display at the National Museum of the United States Air Force at Wright-Patterson Air Force Base in Dayton, Ohio. (Prior to that, they had been kept at the Air Force Academy.)

Cole was not the youngest of the Doolittle Raiders, but the 101-year-old is now the lone survivor after the passing of Staff Sergeant David Thatcher last June. At a ceremony to commemorate the 75th anniversary of the Doolittle Raid at the National Museum of the United States Air Force, not far from where he watched Doolittle circles the skies as a boy, Cole lifted a goblet of cognac aloft and toasted his 79 comrades that were lost on the mission or had passed away since. With that, he turned over Thatcher’s goblet, leaving one silver cup still standing upright.