During the 1925 St. Louis Browns season, Bennett played in 93 games and had a career high six triples with a batting average of .279.

He played in the final of his 312 major league games on October 1, 1927, and finished his career with 13 triples, 13 stolen bases, a .276 batting average, and seven home runs.

[3] At one point during the 1927 season, he crashed into a wall while playing against Philadelphia at Shibe Park, which caused him to fall into a 36-hour coma and helped bring about the end of his major league career.

[2] Bennett became the subject of a feud between Browns owner Phil Ball and commissioner Kenesaw Mountain Landis.

Bennett claimed that his frequent moving in the farm system prevented him from getting a chance to play in the majors, to which Landis ordered Ball to put him on the major league roster or release him, with Ball.