Keeling was born in Owen Sound, Ontario and began his hockey career in his hometown, learning the game at Victoria Public School under the tutelage of principal Henry Kelso, for whom Owen Sound\'s Kelso Beach was named. Several Victoria students, including Keeling, eventually ended up playing for the city\'s junior club, the Owen Sound Greys. He was a key member of the Greys when they captured their first Memorial Cup as Canadian junior hockey champions in 1924, scoring an incredible 37 goals and 46 points in only 15 playoff games.\n', '

Keeling\'s pro career began in 1926–27 with the London Panthers of the Canadian Professional Hockey League, although he was quickly elevated to the NHL\'s Toronto St. Patricks, with whom he had signed as a free agent on September 7, 1926. The St. Pats changed their name to the Maple Leafs later that season. Despite playing in only 30 of Toronto\'s 44 games, Keeling finished fourth in team scoring with 11 goals and 13 points, right behind fellow Owen Sound native Hap Day.\n', '

He repeated that showing in 1927–28, again placing right behind Day, but was traded to the New York Rangers on the eve of the 1928–29 season. He was traded to the New York Rangers on April 16, 1928 in exchange for Alex Gray. Keeling slumped to only six goals and nine points for the Rangers in 1928-29, although he did lead the league in playoff goals and points as the Rangers marched to the final against the Boston Bruins. Boston swept the best-of-three series for its first Stanley Cup win. Among the victorious Bruins was Cooney Weiland, who had starred with Keeling on the 1924 Greys.\n', '

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