As early as , it was apparent that Cronin was nearing the end of his playing career. Red Sox farm director Billy Evans thought he had found Cronin's successor in Pee Wee Reese, the star shortstop for the Louisville Colonels of the Triple-A American Association. He was so impressed by Reese that he was able to talk Yawkey into buying the Colonels and making them the Red Sox' top farm club. However, when Yawkey and Evans asked Cronin to scout Reese, Cronin realized he was scouting his replacement. Believing that he was still had enough left to be a regular player, Cronin deliberately downplayed Reese's talent and suggested that the Red Sox trade him. Reese was eventually traded to the Brooklyn Dodgers, where he went on to a Hall of Fame career. As it turned out, Evans' and Yawkey's initial concerns about Cronin were valid. His last year as a full-time player was ; after that year, he never played more than 76 games per season.