As early as 1938, it was apparent to the Red Sox that Cronin's playing career was nearly over. Red Sox farm system 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 convince Yawkey to buy the Colonels and make them the Red Sox' top farm club. However, when Yawkey and Evans asked Cronin to scout Reese, Cronin realized he was scouting his potential replacement. Believing he still had enough left to be a regular player, Cronin deliberately downplayed Reese's talent and suggested the Red Sox trade him.
After the 1968 season, Cronin drew headlines when he fired AL umpires Al Salerno and Bill Valentine, ostensibly for poor performance; however, it later surfaced that the two officials were fired for attempting to organize an umpires' union.
What a bastard.