He served as the co-pilot to Lieutenant Colonel Jimmy Doolittle in the lead airplane of the raid by sixteen B-25 bombers, which for the first time took off from an aircraft carrier on a bombing mission.

[3][4] Cole enlisted as an aviation cadet in the United States Army Air Forces on November 22, 1940, at Lubbock, Texas.

Cole was co-pilot in the first bomber to depart the deck of the USS Hornet during the mission, and it was piloted by the leader of the raid, then-Lieutenant Colonel Jimmy Doolittle,[7] giving him, and the plane, the very least amount of runway available.

On April 18, 1942, Doolittle and his B-25's four crewmembers, took off from the Hornet, reached Tokyo, Japan, bombed their target,[8] then headed for their recovery airfield in China.

He and his crew linked up after the bailout and were helped through Japanese lines by Chinese guerrillas and American missionary John Birch.

On May 23, 2014, Cole was present in the White House when President of the United States Barack Obama signed a bill on awarding the Congressional Gold Medal to the Doolittle Raiders.

On April 15, 2015, President Obama presented the Congressional Gold Medal to Cole and three other surviving members of the raid, in a ceremony at the White House.

[19][20][4][21] A memorial service for Cole was held at Joint Base San Antonio on April 18, the 77th anniversary of the Doolittle Raid.

His family finally decided to have Cole buried along with his wife at Fort Sam Houston National Cemetery in San Antonio on September 7, 2021, his 106th birthday.