Words that commonly described him as a player were "underrated," "consistent," and "reliable." Keeling was known as a big and strong player, although he was clean and rarely took penalties. He was a solid goal scorer, though not much of a set up man. His best season came in 1936–37 when, playing on a line with Phil Watson and Dillon, he led the Rangers with a career-high 22 goals, the third highest total in the league. In the playoffs he notched three goals and five points before bowing to the Detroit Red Wings.
Keeling was a member of the Rangers 1933 Stanley Cup championship team. In fact it was Keeling who assisted on Bill Cook's famous Stanley Cup winning goal in overtime.