 Traded to the Chicago Cubs before the 1936 season he developed as a competent second baseman.Frey enjoyed his best years with the Cincinnati Reds, helping them to reach two consecutive World Series in 1939 and 1940, after hitting .291 with 11 home runs and 95 runs (1939) and leading the National League with 22 stolen bases (1940) while scoring 102 runs.Five days before the 1940 World Series against Detroit, Frey injured his foot when he dropped the iron lid of the dugout water cooler on it.