Cheshire was soft-spoken, very considerate, thoughtful, unconventional in his thinking, unorthodox, independent minded and no great respecter of authority. On one mission near the end of his tour with 35 Squadron he looked at the route map to the target and noted there would be a great deal of flak over the chosen flight path. Said Cheshire wryly "We took a different route." He was both the youngest group captain in the service and the most decorated. Historian Max Hastings wrote : "Cheshire was a legend in Bomber Command, a remarkable man with an almost mystical air about him, as if he somehow inhabited a different planet from those about him, but without affectation or pretension." Said Flight Sergeant Tom Gallantry, DFC, who served under Cheshire in 76 Squadron: "I felt at the time, and I have always felt, that it was an honour to be a member of his squadron. Everyone felt the same way about him. Air crew... ground crew. He was a terrific character."