[1] In those years, he met and worked with Red Ruffing, helping him transition into a pitcher.
In 1928, the team seized first place after ten games, retaining that position for the rest of the year.
Although many teams were negatively affected by the 1929 Stock Market Crash in 1930, the Generals ended up having their best season, finishing 17 games over the Fairbury Jeffersons.
In 1932, he led the Waterloo Hawks of the Mississippi Valley League to a losing record.
He managed the Lincoln Links of the Nebraska State League for part of 1933 season before being replaced by Jack Hruska.
From 1941 to 1942, Bennett managed the Joplin Miners of the Western Association, another Yankees affiliate.