McCleary attempted a comeback at the start of the 2000–01 season. Despite doubts he would be capable of returning, the Canadiens signed him to a one-year, US$300,000 contract. He appeared in exhibition games with the Canadians, but found he was unable to play a full shift without running short of breath. He was examined by his doctor, who noted that because his air passage was left 15% narrower than before his injury, it was too dangerous for him to continue playing. As a result, on September 20, 2000, McCleary announced his retirement, calling it the "toughest day" in his seven year career. The Canadiens kept him in the organization, naming him a WHL scout.