Born in Kitchener on November 19th, 1928, Kesselring started golfing at an early age. Lloyd Tucker, then Pro at the Rockway Golf Course, assisted him, giving him playing privileges for picking chick weeds out of the greens. He caught on rapidly and won the Ontario Junior Championship in 1945, 1946 and 1948. He missed out in 1947, losing to Bob Fair by one stroke.
He won the Canadian Junior Championship in 1946 and 1947. He was on the Ontario Provincial team for the Willingdon trophy from 1949 to 1953. Kesselring turned professional in October 1953 and in 1960 applied for a return to amateur ranking. Six years later in 1966, his request was granted.
Included in his achievements are the Ontario Open in 1952 and 1953; Ontario Open as a Professional in 1956 and 1957; the Ontario Amateur Championship in 1949, 1951, 1952 and 1953. He was chosen Ontario's most outstanding athlete in 1952 by the Ontario Sportswriter and Broadcasters Association.